JP6846430B2 - 鉱酸によってイソシアネートに基づくキセロゲルおよびエアロゲルを作製するための方法 - Google Patents
鉱酸によってイソシアネートに基づくキセロゲルおよびエアロゲルを作製するための方法 Download PDFInfo
- Publication number
- JP6846430B2 JP6846430B2 JP2018538932A JP2018538932A JP6846430B2 JP 6846430 B2 JP6846430 B2 JP 6846430B2 JP 2018538932 A JP2018538932 A JP 2018538932A JP 2018538932 A JP2018538932 A JP 2018538932A JP 6846430 B2 JP6846430 B2 JP 6846430B2
- Authority
- JP
- Japan
- Prior art keywords
- composition
- solvent
- gel
- mixture
- porous material
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims description 70
- 239000002253 acid Substances 0.000 title claims description 38
- 229910052500 inorganic mineral Inorganic materials 0.000 title claims description 30
- 239000011707 mineral Substances 0.000 title claims description 30
- 150000007513 acids Chemical class 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims description 130
- 239000011148 porous material Substances 0.000 claims description 118
- 239000002904 solvent Substances 0.000 claims description 98
- 239000012948 isocyanate Substances 0.000 claims description 48
- 150000002513 isocyanates Chemical class 0.000 claims description 42
- 238000001035 drying Methods 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 22
- 239000007788 liquid Substances 0.000 claims description 21
- -1 alicyclic halogenated hydrocarbon Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000011651 chromium Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 229910052785 arsenic Inorganic materials 0.000 claims description 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052804 chromium Inorganic materials 0.000 claims description 4
- 150000001983 dialkylethers Chemical class 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000011630 iodine Substances 0.000 claims description 4
- 150000004715 keto acids Chemical class 0.000 claims description 4
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 239000011574 phosphorus Substances 0.000 claims description 4
- 229910052711 selenium Inorganic materials 0.000 claims description 4
- 239000011669 selenium Substances 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052713 technetium Inorganic materials 0.000 claims description 4
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical compound [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052714 tellurium Inorganic materials 0.000 claims description 4
- PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052720 vanadium Inorganic materials 0.000 claims description 4
- 150000004292 cyclic ethers Chemical class 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 150000005677 organic carbonates Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 239000012774 insulation material Substances 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 57
- 239000000499 gel Substances 0.000 description 56
- 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 42
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
- 238000001879 gelation Methods 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 16
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 16
- 239000000243 solution Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000463 material Substances 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 235000011089 carbon dioxide Nutrition 0.000 description 8
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 8
- 229920002396 Polyurea Polymers 0.000 description 7
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 7
- 239000011810 insulating material Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 7
- 238000003980 solgel method Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 3
- 239000008240 homogeneous mixture Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 3
- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 3
- 239000007791 liquid phase Substances 0.000 description 3
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920001184 polypeptide Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 3
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-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
- KEFJLCGVTHRGAH-UHFFFAOYSA-N 2-acetyl-5-methylfuran Chemical compound CC(=O)C1=CC=C(C)O1 KEFJLCGVTHRGAH-UHFFFAOYSA-N 0.000 description 2
- RMGHERXMTMUMMV-UHFFFAOYSA-N 2-methoxypropane Chemical compound COC(C)C RMGHERXMTMUMMV-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-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
- 238000001321 HNCO Methods 0.000 description 2
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- 229910004283 SiO 4 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 description 2
- RBQRWNWVPQDTJJ-UHFFFAOYSA-N methacryloyloxyethyl isocyanate Chemical compound CC(=C)C(=O)OCCN=C=O RBQRWNWVPQDTJJ-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- ZZXUZKXVROWEIF-UHFFFAOYSA-N 1,2-butylene carbonate Chemical compound CCC1COC(=O)O1 ZZXUZKXVROWEIF-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
- 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
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-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
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- RTJGBIGSNVJSDM-UHFFFAOYSA-N 1-(2-isocyanatopropan-2-yl)-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C(C)(C)N=C=O)=C1 RTJGBIGSNVJSDM-UHFFFAOYSA-N 0.000 description 1
- LTIKIBFTASQKMM-UHFFFAOYSA-N 1-[bis(4-isocyanatophenyl)methyl]-4-isocyanatobenzene Chemical compound C1=CC(N=C=O)=CC=C1C(C=1C=CC(=CC=1)N=C=O)C1=CC=C(N=C=O)C=C1 LTIKIBFTASQKMM-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
- 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
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 1
- XOOBTEUBXZXNKK-UHFFFAOYSA-N 2-methoxy-4-methylpentane Chemical compound COC(C)CC(C)C XOOBTEUBXZXNKK-UHFFFAOYSA-N 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
- PSBKJPTZCVYXSD-UHFFFAOYSA-N 5-methylheptan-3-one Chemical compound CCC(C)CC(=O)CC PSBKJPTZCVYXSD-UHFFFAOYSA-N 0.000 description 1
- BOPCAWBPVSVBMM-UHFFFAOYSA-N 6-methylcyclohex-3-ene-1-carbaldehyde Chemical compound CC1CC=CCC1C=O BOPCAWBPVSVBMM-UHFFFAOYSA-N 0.000 description 1
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-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
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-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
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 239000006096 absorbing agent Substances 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
- 230000003044 adaptive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 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
- 239000003139 biocide Substances 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method 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
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-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
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-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
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010191 image analysis Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 239000002923 metal particle Substances 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FXADMRZICBQPQY-UHFFFAOYSA-N orthotelluric acid Chemical compound O[Te](O)(O)(O)(O)O FXADMRZICBQPQY-UHFFFAOYSA-N 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
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 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
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229920013730 reactive polymer Polymers 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- MCAHWIHFGHIESP-UHFFFAOYSA-N selenous acid Chemical compound O[Se](O)=O MCAHWIHFGHIESP-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
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000000352 supercritical drying Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 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
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 239000011240 wet gel Substances 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
- C08G18/08—Processes
- C08G18/14—Manufacture of cellular products
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/20—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state
- B01J35/23—Catalysts, in general, characterised by their form or physical properties characterised by their non-solid state in a colloidal state
-
- 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
- C08G18/08—Processes
- C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
- C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
- C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
- C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/703—Isocyanates or isothiocyanates transformed in a latent form by physical means
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/24—Acids; Salts thereof
-
- 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)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Dispersion Chemistry (AREA)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Description
a) 混合物(I)を用意する工程であって、混合物(I)は、
(i) 組成物(A)であって、
成分(ai)としての少なくとも1種の多官能性イソシアネートと、
少なくとも1種の鉱酸(aa)と
を少なくとも含む、組成物(A)
および
(ii) 溶媒(B)
を含む、工程、
b) 組成物(A)中の成分を反応させ、有機ゲルを得る工程ならびに
c) 得られたゲルを乾燥させる工程
を少なくとも含む、方法によって解決される。
− 0〜2wt%の範囲の量のアミン、
− 0〜20wt%の範囲の量のアルコールおよび
− 0〜1wt%の範囲の量の水
を含む、上記に開示の多孔性材料を製造するための方法を対象とする。
i) トリレンジイソシアネート(TDI)、特に2,4−TDIもしくは2,6−TDIまたは2,4−および2,6−TDIの混合物を主体とした多官能性イソシアネート、
ii) ジフェニルメタンジイソシアネート(MDI)、特に2,2’−MDIもしくは2,4’−MDIもしくは4,4’−MDI、もしくは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オリゴメリックMDI、もしくは上述したジフェニルメタンジイソシアネートの2種もしくは3種の混合物、もしくはMDIの作製において得られた粗製MDI、または少なくとも1種のMDIのオリゴマーと上述した低分子量MDI誘導体の少なくとも1種との混合物を主体とした多官能性イソシアネート、
iii) トリス(4−イソシアナトフェニル)メタン(TIPM)、
iv) 実施形態i)による少なくとも1種の芳香族イソシアネートと、実施形態ii)による少なくとも1種の芳香族イソシアネートとの混合物
である。
組成物(A)は、成分(ac)としての少なくとも1種の触媒をさらに含み得る。使用される成分(ac)の量は、好ましくは少なくとも0.1質量%、特に少なくとも0.2質量%、特に好ましくは少なくとも0.3質量%、特に少なくとも0.5質量%である。使用される成分(ac)の量は、いずれの場合においても組成物(A)の総質量に対して、好ましくは最大で20質量%、特に最大で18質量%、特に好ましくは最大で16質量%、特に最大で14質量%である。
本発明によれば、反応は、溶媒(B)の存在下で起きる。
本発明の方法は、
(a) 上記に記載した組成物(A)および溶媒(B)を含む混合物を用意する工程、
(b) 溶媒(B)の存在下で組成物(A)中の成分を反応させて、ゲルを形成する工程ならびに
(c) 工程(b)において得られたゲルを乾燥させる工程
を少なくとも含む。
本発明によれば、組成物(A)および溶媒(B)を含む混合物が、工程(a)において用意される。
本発明によれば、工程(b)において、組成物(A)の成分の反応が、溶媒(B)の存在下で起きて、ゲルを形成する。反応を実施するためには、最初に、工程(a)において用意される成分の均一な混合物を作製しなければならない。工程(a)において用意される成分の用意は、従来の方法によって実施することができる。ここで、好ましくは、撹拌器具または別の混合器具が、良好で迅速な混合を達成するために使用される。均一な混合物を作製するために必要な時間は、混合不良を回避するために、ゲル化反応によりゲルの少なくとも部分的な形成が起きる時間より短くすべきである。他の混合条件は一般に重要ではなく、例えば、混合は、0〜100℃および0.1〜10bar(絶対圧)において実施することができ、特に、例えば室温および大気圧において実施することができる。均一な混合物が作成された後には、混合装置のスイッチを切ることが好ましい。
本発明によれば、工程(b)において得られたゲルは、工程(c)において乾燥される。
本発明は、本発明の方法によって得ることができる多孔性材料をさらに提供する。エアロゲルは、本発明の目的のための多孔性材料として好ましく、すなわち、本発明によって得ることができる多孔性材料は、好ましくは、エアロゲルである。
a) 混合物(I)を用意する工程であって、混合物(I)は、
(i) 組成物(A)であって、
成分(ai)としての少なくとも1種の多官能性イソシアネートと、
少なくとも1種の鉱酸(aa)と
を少なくとも含む、組成物(A)
および
(ii) 溶媒(B)
を含む、工程
b) 組成物(A)中の成分を反応させ、有機ゲルを得る工程ならびに
c) 得られたゲルを乾燥させる工程
を少なくとも含む、方法。
− 0〜2wt%の範囲の量のアミン、
− 0〜20wt%の範囲の量のアルコールおよび
− 0〜1wt%の範囲の量の水
を含む、実施形態1による方法。
Desmodur RE(登録商標):M105−ISO11909に従った9.3±0.2%のNCO含量、およそ3の官能性およびDIN53015に従った20℃において3mPa.sの粘度を有する、酢酸エチル中の約27%トリフェニルメタン−4,4’,4”−トリイソシアネート(TIPM)の溶液。
2.1 物理的特性決定
バルク密度(ρb)を、試料の質量および物理的寸法から計算した。Micromeritics AccuPyc II1340機器を使用して、ヘリウムピクノメトリーによって、骨格密度(ρs)を測定した。
細孔サイズが1.7〜300nmの範囲である場合のBET表面積および細孔サイズ分布を、Micromeritics ASAP2020という表面積および多孔度の分析装置を使用して、77KにおけるN2収着ポロシメトリーによって測定した。Micromeritics Tristar II3020バージョン3.02を使用して、0℃において、760torr(0.03の相対圧力)に至るまでのCO2収着によって、ミクロ細孔分析を実施した。
3.1 多孔性材料BPUA−xを作製するための好ましい手順
一般的な手順において、H3BO3(0.61g、0.01mol)を無水DMF中に溶解させ、溶液を13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に加えた。得られたゾルを室温においてN2中で15分撹拌し、(Wheaton 4mLポリプロピレン製Omni−Vials 内径1.04cm、Fisher部品番号225402)に注ぎ込み、次いで、この型を密封し、ゲル化のために放置した。ゾル中のモノマー(TIPM+H3BO3)の合計質量パーセント濃度は、溶媒(DMF)の量の変更によって変更したが、試料の名称では、添え字−xによって表されている。BPUA−xのゲル化を室温で実施した。すべての処方およびゲル化時間を、表1に要約する。ゲルを室温において型の中で12時間エージングし、型から取り出し、DMF(2倍)およびアセトン(4倍、毎回の洗浄でゲルの体積の4倍を使用する)によって洗浄し、液体CO2が超臨界流体(SCF)として抜き出されるオートクレーブ内で乾燥させた。
一般的な手順において、13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)、H2O(0.54g、0.03mol)および無水DMFの溶液の質量に対して0.3%w/wのEt3Nを加えた。得られたゾルを室温においてN2中で10分撹拌し、型(Wheaton 4mLポリプロピレン製Omni−Vials 内径1.04cm、Fisher部品番号225402)に注ぎ込み、この型を密封し、ゲル化のために室温で放置した。ゾル中のモノマー(TIPM+H2O)の合計質量パーセント濃度は、溶媒(DMF)の量の変更によって変更したが、試料の名称では、添え字−yによって表されている。すべての処方およびゲル化時間を、表に要約する。ゲルを室温において型の中で12時間エージングした。続いて、ゲルを型から取り出し、DMF(2倍)、アセトン(4倍、毎回の洗浄でゲルの体積の4倍を使用する)によって洗浄し、液体CO2がSCFとして抜き出されるオートクレーブ内で乾燥させた。
超臨界流体(SCF)CO2による湿潤ゲルの乾燥を、オートクレーブ(SPIDRY Jumbo Supercritical Point Dryer、SPI Supplies,Inc.West Chester、PAまたはSpeedSFEシステム、Applied Separations、Allentown、PA)内で実施した。試料をオートクレーブに装入し、すべての試料が沈み込むまでアセトンを加えた。加圧容器を閉じ、液体CO2がすべてのアセトンを置きかえ、これらのアセトンが排出されるまで液体CO2を室温で導入した。すべてのアセトンが試料の細孔から抜き出されるまで、液体CO2をさらに数回容器に導入した。この時点でCO2が出現し始め、ドライアイスを形成した。続いて、オートクレーブの温度を40℃に上昇させ、SCFCO2を気体として逃がした。
4.1 一般手順
リン酸(純粋)をAcros Organicsから購入し、リン酸(98%)をAlfa Aesarから購入し、テルル酸(99%以上)、亜セレン酸(98%)、過ヨウ素酸(99%以上)および金酸をSigma−Aldrichから購入した。すべてのゾルは、モノマー(TIPM+鉱酸)の質量パーセントが16%の一定に保持されるように配合した。すべての処方およびゲル化時間を、表S.9に要約する。材料特性決定データを、表S.10に示す。具体的には、下記のとおりである。
H3PO4(0.98g、0.010mol)を無水DMSO(13.1mL、14.5g)中に溶解させ、溶液をドライアイス/アセトン浴(−78℃)中で冷却した。この溶液を解凍したら、冷たい(−78℃の)13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に加え、混合物を激しく撹拌した。
H3PO3(1.23g、0.015mol)を無水DMSO(14.3mL、15.8g)中に溶解させ、溶液をドライアイス/アセトン浴(−78℃)中で冷却した。この溶液を解凍したら、冷たい(−78℃の)13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に加え、混合物を激しく撹拌した。
H2SeO3(1.93g、0.015mol)を無水DMF(20.5mL、19.4g)中に溶解させ、溶液をドライアイス/アセトン浴(−78℃)中で冷却した。冷たい溶液を、冷たい(−78℃の)13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に加え、混合物を激しく撹拌した。
Te(OH)6(1.14g、0.005mol)を無水DMF(16.1mL、15.3g)中に溶解させ、溶液を13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に室温で加え、混合物を激しく撹拌した。
H5IO6(1.36g、0.006mol)を無水DMF(17.3mL、16.4g)中に溶解させ、溶液を13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に室温で加え、混合物を激しく撹拌した。
H3AuO3(2.48g、0.01mol)を無水DMF(112.5mL、106.9g)中に溶解させ、溶液を13.6gのDesmodur RE(3.67g、0.01molのTIPMを含有する)に室温で加え、混合物を激しく撹拌した。
Claims (7)
- 多孔性材料を製造するための方法であって、
a) 混合物(I)を用意する工程であって、混合物(I)は、
(i) 組成物(A)であって、
成分(ai)としての少なくとも1種の多官能性イソシアネートと、
少なくとも1種の鉱酸(aa)と
を少なくとも含む、組成物(A)
および
(ii) 溶媒(B)
を含む、工程、
b) 組成物(A)中の成分を反応させ、有機ゲルを得る工程ならびに
c) 得られたゲルを乾燥させる工程
を少なくとも含み、
鉱酸(aa)が、硫黄、ホウ素、窒素、リン、ケイ素、塩素、臭素、ヨウ素またはフッ素、クロム、バナジウム、マンガン、レニウム、テクネチウム、ヒ素、セレンまたはテルルを含む無機オキソ酸からなる群より選択され、
前記組成物(A)が、40〜99mol%の範囲の量の成分(ai)を含み、且つ
前記溶媒(B)が、ケトン、アルデヒド、アルキルアルカノエート、アセタール、ジアルキルエーテル、環状エーテル、アミド、スルホキシド、脂肪族又は脂環式ハロゲン化炭化水素、ハロゲン化芳香族化合物、有機カーボネート及びフッ素含有エーテル、並びにこれら溶媒の2種以上の混合物より選択される、
方法。 - 組成物(A)が、
− 0〜2wt%の範囲の量のアミン、
− 0〜20wt%の範囲の量のアルコールおよび
− 0〜1wt%の範囲の量の水
(但し、0を除く)
を含む、請求項1に記載の方法。 - 多官能性イソシアネートが、芳香族、脂肪族、脂環式および芳香脂肪族イソシアネートからなる群より選択される、請求項1または2に記載の方法。
- 組成物(A)が、60〜1mol%の範囲の量の鉱酸(aa)を含む、請求項1から3のいずれか一項に記載の方法。
- 工程c)による乾燥が、ゲルに含まれる液体の臨界温度および臨界圧力より低い温度および圧力において、ゲルに含まれる液体を気体状態に変換することによって実施される、請求項1から4のいずれか一項に記載の方法。
- 断熱材料としてまたは真空絶縁パネルのために、請求項1から5のいずれか一項に記載の方法によって得られるもしくは得ることができる多孔性材料を使用する方法。
- 触媒として、請求項1から5のいずれか一項に記載の方法によって得られるもしくは得ることができる多孔性材料を使用する方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562242324P | 2015-10-16 | 2015-10-16 | |
EP15190183.2 | 2015-10-16 | ||
US62/242,324 | 2015-10-16 | ||
EP15190183 | 2015-10-16 | ||
PCT/EP2016/074308 WO2017064044A1 (en) | 2015-10-16 | 2016-10-11 | Process for producing isocyanate-based xerogels and aerogels with mineral acids |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2018532035A JP2018532035A (ja) | 2018-11-01 |
JP6846430B2 true JP6846430B2 (ja) | 2021-03-24 |
Family
ID=54539814
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018538932A Active JP6846430B2 (ja) | 2015-10-16 | 2016-10-11 | 鉱酸によってイソシアネートに基づくキセロゲルおよびエアロゲルを作製するための方法 |
Country Status (6)
Country | Link |
---|---|
US (1) | US10759893B2 (ja) |
EP (1) | EP3362497B1 (ja) |
JP (1) | JP6846430B2 (ja) |
KR (1) | KR20180069864A (ja) |
CN (1) | CN108350142B (ja) |
WO (1) | WO2017064044A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN115895414B (zh) * | 2022-12-01 | 2023-08-04 | 华阳新材料科技集团有限公司 | 一种单组份聚脲防腐隔热涂料的制备方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5478867A (en) | 1993-07-07 | 1995-12-26 | The Dow Chemical Company | Microporous isocyanate-based polymer compositions and method of preparation |
JP2000001560A (ja) * | 1998-06-12 | 2000-01-07 | Sanyo Chem Ind Ltd | 無機有機複合発泡体及びその製造法 |
AU5862099A (en) | 1998-10-22 | 2000-05-15 | Huntsman Ici Chemicals Llc | Insulated bodies |
US20090280329A1 (en) * | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US20090283480A1 (en) * | 2006-06-20 | 2009-11-19 | Basf Se | Porous material with a nonoporous coating |
DE502008003187D1 (de) | 2007-08-28 | 2011-05-26 | Basf Se | Xerogele auf basis von polyharnstoff |
JP2012520386A (ja) * | 2009-03-16 | 2012-09-06 | ビーエーエスエフ ソシエタス・ヨーロピア | キセロゲル複合材料の製造方法 |
PL2510026T3 (pl) | 2009-12-11 | 2014-07-31 | Basf Se | Ulepszone porowate materiały na bazie amin aromatycznych |
EP2399945A1 (de) | 2010-06-28 | 2011-12-28 | Basf Se | Verfahren zur Herstellung von Porösen materialien auf basis von Polyharnstoff |
US10301445B2 (en) | 2010-08-20 | 2019-05-28 | Aerogel Technologies, Llc | Three-dimensional porous polyurea networks and methods of manufacture |
EP2635616B1 (de) | 2010-11-04 | 2017-08-02 | Basf Se | Verfahren zur herstellung von aerogelen oder xerogelen |
US9188384B2 (en) * | 2011-03-31 | 2015-11-17 | Basf Se | Dynamically evacuable devices comprising organic aerogels or xerogels |
CN102432907B (zh) * | 2011-08-17 | 2013-01-23 | 浙江恒泰源聚氨酯有限公司 | 抗低温耐寒聚氨酯双组分鞋底原料的制备方法 |
CN103319719B (zh) * | 2012-03-19 | 2015-07-22 | 香港纺织及成衣研发中心有限公司 | 一种智能应力响应型硅硼聚合物微凝胶的制备方法 |
-
2016
- 2016-10-11 KR KR1020187013579A patent/KR20180069864A/ko not_active Application Discontinuation
- 2016-10-11 EP EP16779113.6A patent/EP3362497B1/en active Active
- 2016-10-11 US US15/767,710 patent/US10759893B2/en active Active
- 2016-10-11 JP JP2018538932A patent/JP6846430B2/ja active Active
- 2016-10-11 CN CN201680059334.3A patent/CN108350142B/zh active Active
- 2016-10-11 WO PCT/EP2016/074308 patent/WO2017064044A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
CN108350142B (zh) | 2021-07-23 |
JP2018532035A (ja) | 2018-11-01 |
WO2017064044A1 (en) | 2017-04-20 |
KR20180069864A (ko) | 2018-06-25 |
US10759893B2 (en) | 2020-09-01 |
CN108350142A (zh) | 2018-07-31 |
EP3362497A1 (en) | 2018-08-22 |
US20180305491A1 (en) | 2018-10-25 |
EP3362497B1 (en) | 2019-09-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP5937606B2 (ja) | エアロゲル又はキセロゲルの製造方法 | |
JP5770202B2 (ja) | 芳香族アミン系の多孔質材料の改善品 | |
JP5882314B2 (ja) | 多孔質ポリウレア系材料の製造方法 | |
US8741976B2 (en) | Process for producing aerogels or xerogels | |
CA3004784C (en) | (super)hydrophobic isocyanate based porous materials | |
US8785512B2 (en) | Porous gels based on aromatic and cycloaliphatic amines | |
CN108137781B (zh) | 具有降低的密度的基于异氰酸酯的有机干凝胶 | |
KR20160136414A (ko) | 다공질 재료의 제조 방법 | |
JP2022023135A (ja) | 多孔質材料の製造方法 | |
KR20160057461A (ko) | 이소시아네이트계 유기 에어로겔의 제조 방법 | |
JP6846430B2 (ja) | 鉱酸によってイソシアネートに基づくキセロゲルおよびエアロゲルを作製するための方法 | |
CN107810218B (zh) | 功能化的基于异氰酸酯的多孔材料 | |
JP6955813B2 (ja) | 多孔性材料を作製するための方法 | |
JP2020526651A (ja) | 優れた可逆的吸水の多孔質物質 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A529 | Written submission of copy of amendment under article 34 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A529 Effective date: 20180605 |
|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20191011 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20200915 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20201006 |
|
A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20210105 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20210115 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20210202 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20210301 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6846430 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |