CN104163906B - 一种用于异氰酸酯三聚，异氰酸酯与环氧成环反应的催化剂及其应用 - Google Patents
一种用于异氰酸酯三聚，异氰酸酯与环氧成环反应的催化剂及其应用 Download PDFInfo
- Publication number
- CN104163906B CN104163906B CN201410082417.7A CN201410082417A CN104163906B CN 104163906 B CN104163906 B CN 104163906B CN 201410082417 A CN201410082417 A CN 201410082417A CN 104163906 B CN104163906 B CN 104163906B
- Authority
- CN
- China
- Prior art keywords
- catalyst
- chromium
- epoxy
- reaction
- isocyanate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 56
- 239000012948 isocyanate Substances 0.000 title claims abstract description 48
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 42
- 239000004593 Epoxy Substances 0.000 title claims abstract description 26
- 238000005829 trimerization reaction Methods 0.000 title claims abstract description 9
- 238000010719 annulation reaction Methods 0.000 title 1
- 239000011651 chromium Substances 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 239000003426 co-catalyst Substances 0.000 claims abstract description 10
- 229920000642 polymer Polymers 0.000 claims abstract description 10
- 150000007530 organic bases Chemical class 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 230000035484 reaction time Effects 0.000 claims abstract description 4
- -1 aralkyl carboxylate Chemical class 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical class CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 8
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000000376 reactant Substances 0.000 claims description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 238000006555 catalytic reaction Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- CNIGXAJYMNFRCZ-UHFFFAOYSA-K butanoate;chromium(3+) Chemical compound [Cr+3].CCCC([O-])=O.CCCC([O-])=O.CCCC([O-])=O CNIGXAJYMNFRCZ-UHFFFAOYSA-K 0.000 claims description 3
- PYXSPTLIBJZHQW-UHFFFAOYSA-K chromium(3+);propanoate Chemical compound [Cr+3].CCC([O-])=O.CCC([O-])=O.CCC([O-])=O PYXSPTLIBJZHQW-UHFFFAOYSA-K 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- IVKVYYVDZLZGGY-UHFFFAOYSA-K chromium(3+);octadecanoate Chemical compound [Cr+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O IVKVYYVDZLZGGY-UHFFFAOYSA-K 0.000 claims description 2
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical class O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 claims 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 150000002118 epoxides Chemical class 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims 1
- FQHYQCXMFZHLAE-UHFFFAOYSA-N 25405-85-0 Chemical compound CC1(C)C2(OC(=O)C=3C=CC=CC=3)C1C1C=C(CO)CC(C(C(C)=C3)=O)(O)C3C1(O)C(C)C2OC(=O)C1=CC=CC=C1 FQHYQCXMFZHLAE-UHFFFAOYSA-N 0.000 claims 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 1
- DXRFZHILMCWCNG-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-2-amine Chemical compound C1=CC=NC2=NC(N(C)C)=CC=C21 DXRFZHILMCWCNG-UHFFFAOYSA-N 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- ZWVDDNPNPYXFKA-KVVVOXFISA-N chromium;(z)-octadec-9-enoic acid Chemical compound [Cr].CCCCCCCC\C=C/CCCCCCCC(O)=O ZWVDDNPNPYXFKA-KVVVOXFISA-N 0.000 claims 1
- UKNOHKMMYBIXMI-UHFFFAOYSA-N chromium;decanoic acid Chemical compound [Cr].CCCCCCCCCC(O)=O UKNOHKMMYBIXMI-UHFFFAOYSA-N 0.000 claims 1
- XZFHHYUTHSXZQQ-UHFFFAOYSA-N chromium;pentanoic acid Chemical compound [Cr].CCCCC(O)=O XZFHHYUTHSXZQQ-UHFFFAOYSA-N 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002916 oxazoles Chemical class 0.000 claims 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- QVTVDJWJGGEOGX-UHFFFAOYSA-N urea;cyanide Chemical compound N#[C-].NC(N)=O QVTVDJWJGGEOGX-UHFFFAOYSA-N 0.000 claims 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 abstract description 18
- 125000003700 epoxy group Chemical group 0.000 abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- 238000010521 absorption reaction Methods 0.000 description 14
- 230000003197 catalytic effect Effects 0.000 description 13
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 10
- 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 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 5
- RPBPCPJJHKASGQ-UHFFFAOYSA-K chromium(3+);octanoate Chemical compound [Cr+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O RPBPCPJJHKASGQ-UHFFFAOYSA-K 0.000 description 5
- 238000010907 mechanical stirring Methods 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- DWGGKKBVZVJZDK-UHFFFAOYSA-N C(C1=CC=CC=C1)C(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Br Chemical compound C(C1=CC=CC=C1)C(C=CC=C1)=C1P(C1=CC=CC=C1)C1=CC=CC=C1.Br DWGGKKBVZVJZDK-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-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
- 239000007788 liquid Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- WTAGBGKFGMJZNM-UHFFFAOYSA-N n,n-diethyl-3-phenylpropan-1-amine;hydrochloride Chemical compound Cl.CCN(CC)CCCC1=CC=CC=C1 WTAGBGKFGMJZNM-UHFFFAOYSA-N 0.000 description 3
- 238000007142 ring opening reaction Methods 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
- 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
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WYYQVWLEPYFFLP-UHFFFAOYSA-K chromium(3+);triacetate Chemical compound [Cr+3].CC([O-])=O.CC([O-])=O.CC([O-])=O WYYQVWLEPYFFLP-UHFFFAOYSA-K 0.000 description 2
- OXMLCJOPQGRRKV-UHFFFAOYSA-K chromium(3+);tribenzoate Chemical compound [Cr+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 OXMLCJOPQGRRKV-UHFFFAOYSA-K 0.000 description 2
- NPCUWXDZFXSRLT-UHFFFAOYSA-N chromium;2-ethylhexanoic acid Chemical compound [Cr].CCCCC(CC)C(O)=O NPCUWXDZFXSRLT-UHFFFAOYSA-N 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 229920000582 polyisocyanurate Polymers 0.000 description 2
- 239000011495 polyisocyanurate Substances 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 229920006389 polyphenyl polymer Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 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
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- MQXNNWDXHFBFEB-UHFFFAOYSA-N 2,2-bis(2-hydroxyphenyl)propane Chemical compound C=1C=CC=C(O)C=1C(C)(C)C1=CC=CC=C1O MQXNNWDXHFBFEB-UHFFFAOYSA-N 0.000 description 1
- KCAMLFCTSSYIFW-UHFFFAOYSA-N 2,4,6-tris(dimethylamino)phenol Chemical compound CN(C)C1=CC(N(C)C)=C(O)C(N(C)C)=C1 KCAMLFCTSSYIFW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- SSIZLKDLDKIHEV-UHFFFAOYSA-N 2,6-dibromophenol Chemical compound OC1=C(Br)C=CC=C1Br SSIZLKDLDKIHEV-UHFFFAOYSA-N 0.000 description 1
- QFZKVFCEJRXRBD-UHFFFAOYSA-N 2-ethyl-4-[(2-ethyl-5-methyl-1h-imidazol-4-yl)methyl]-5-methyl-1h-imidazole Chemical compound N1C(CC)=NC(CC2=C(NC(CC)=N2)C)=C1C QFZKVFCEJRXRBD-UHFFFAOYSA-N 0.000 description 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- GEMWDXVZXZBXDG-UHFFFAOYSA-N 3-(cycloocten-1-yl)-1,4,5,6,7,8-hexahydrodiazocine Chemical compound C1CCCCCC(C=2CCCCCNN=2)=C1 GEMWDXVZXZBXDG-UHFFFAOYSA-N 0.000 description 1
- YSWBFLWKAIRHEI-UHFFFAOYSA-N 4,5-dimethyl-1h-imidazole Chemical compound CC=1N=CNC=1C YSWBFLWKAIRHEI-UHFFFAOYSA-N 0.000 description 1
- NELFWLUXURRZAY-UHFFFAOYSA-N 4-ethyl-2,5-dimethyl-1h-imidazole Chemical compound CCC=1N=C(C)NC=1C NELFWLUXURRZAY-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 1
- NLEQBGSJXDFIEZ-UHFFFAOYSA-N CONC1=CC=CC=C1.N=C=O.N=C=O Chemical compound CONC1=CC=CC=C1.N=C=O.N=C=O NLEQBGSJXDFIEZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OMRDSWJXRLDPBB-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1 OMRDSWJXRLDPBB-UHFFFAOYSA-N 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241001652963 Speranza Species 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- JYNMIXFGWAQWLU-UHFFFAOYSA-N [I-].CCC1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [I-].CCC1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 JYNMIXFGWAQWLU-UHFFFAOYSA-N 0.000 description 1
- DUVKXNKIYKAUPK-UHFFFAOYSA-N acetic acid;triphenylphosphane Chemical compound CC(O)=O.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 DUVKXNKIYKAUPK-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- KWQLUUQBTAXYCB-UHFFFAOYSA-K antimony(3+);triiodide Chemical compound I[Sb](I)I KWQLUUQBTAXYCB-UHFFFAOYSA-K 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940046374 chromium picolinate Drugs 0.000 description 1
- YMZYRUGVHTYUBH-GNOQXXQHSA-K chromium(3+) (Z)-octadec-9-enoate Chemical compound [Cr+3].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O YMZYRUGVHTYUBH-GNOQXXQHSA-K 0.000 description 1
- AITAOEOXKILIIK-UHFFFAOYSA-K chromium(3+) hexanoate Chemical compound [Cr+3].CCCCCC([O-])=O.CCCCCC([O-])=O.CCCCCC([O-])=O AITAOEOXKILIIK-UHFFFAOYSA-K 0.000 description 1
- WFOOTRPLCMPWIP-UHFFFAOYSA-K chromium(3+) pentanoate Chemical compound [Cr+3].CCCCC([O-])=O.CCCCC([O-])=O.CCCCC([O-])=O WFOOTRPLCMPWIP-UHFFFAOYSA-K 0.000 description 1
- LJAOOBNHPFKCDR-UHFFFAOYSA-K chromium(3+) trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Cl-].[Cr+3] LJAOOBNHPFKCDR-UHFFFAOYSA-K 0.000 description 1
- OPFVVBAXBSHTKD-UHFFFAOYSA-K chromium(3+);decanoate Chemical compound [Cr+3].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O OPFVVBAXBSHTKD-UHFFFAOYSA-K 0.000 description 1
- GJYSUGXFENSLOO-UHFFFAOYSA-N chromium;pyridine-2-carboxylic acid Chemical compound [Cr].OC(=O)C1=CC=CC=N1.OC(=O)C1=CC=CC=N1.OC(=O)C1=CC=CC=N1 GJYSUGXFENSLOO-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- DLAHAXOYRFRPFQ-UHFFFAOYSA-N dodecyl benzoate Chemical compound CCCCCCCCCCCCOC(=O)C1=CC=CC=C1 DLAHAXOYRFRPFQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 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 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- GTCDARUMAMVCRO-UHFFFAOYSA-M tetraethylazanium;acetate Chemical compound CC([O-])=O.CC[N+](CC)(CC)CC GTCDARUMAMVCRO-UHFFFAOYSA-M 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- WHAFDJWJDDPMDO-UHFFFAOYSA-N trimethyl(phenyl)phosphanium Chemical compound C[P+](C)(C)C1=CC=CC=C1 WHAFDJWJDDPMDO-UHFFFAOYSA-N 0.000 description 1
- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229940102001 zinc bromide Drugs 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/794—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aromatic isocyanates or isothiocyanates
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0237—Amines
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0244—Nitrogen containing compounds with nitrogen contained as ring member in aromatic compounds or moieties, e.g. pyridine
-
- 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
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
-
- 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
- B01J31/04—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing carboxylic acids or their salts
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
- C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/222—Catalysts containing metal compounds metal compounds not provided for in groups C08G18/225 - C08G18/26
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
-
- 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
- C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
-
- 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
- C08G2115/00—Oligomerisation
- C08G2115/02—Oligomerisation to isocyanurate groups
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)
- Materials Engineering (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
本发明涉及一种可催化异氰酸酯三聚反应形成异氰脲酸酯，异氰酸酯与环氧反应形成恶唑烷酮的催化剂。该催化剂以取代或未取代的、直链或支链的、烷基的、芳基或者芳烷基的C3‑C60羧酸铬（Cr+3）为主催化剂，以有机碱为助催化剂，通过改变主催化剂和助催化剂的比例及用量、原料摩尔比、反应温度以及反应时间等，合成得到含异氰脲酸酯环/恶唑烷酮环的端环氧基或端异氰酸酯基的齐聚物、低聚物及高聚物等结构性能可控的材料，其中异氰脲酸酯/恶唑烷酮的质量比为0:100~100:0可调。
Description
技术领域
本发明涉及一种羧酸铬(Cr+3)催化剂，在有机碱的协助下，可催化异氰酸酯的三聚反应，合成得到异氰脲酸酯；也可催化异氰酸酯与环氧反应，形成恶唑烷酮。通过该反应可将异氰脲酸酯/恶唑烷酮结构引入到聚合物材料中，应用于如涂料、胶黏剂、密封胶和复合材料树脂基体，提高材料的强度、耐热性、与填料的粘结性以及介电性能等。
背景技术
本发明主要针对在一定温度下，羧酸铬(Cr+3)催化异氰酸酯的三聚反应生成异氰脲酸酯环(Isocyanate,IS)和异氰酸酯与环氧开环反应生成恶唑烷酮环(Oxazolidone,OX)。Kordomenos等研究表明，聚异氰脲酸酯(PIS)的热分解温度为380～420℃，聚恶唑烷酮(POX)的热分解温度为330～360℃，增加材料中这两种刚性环的含量可提高材料的热性能。其中，IS在催化剂作用下可低温合成得到，而OX的合成条件则比较苛刻，只有在130℃以上的高温以及合适的催化剂存在下才会发生。因此，寻找可低温催化OX生成的催化剂具有重要的现实意义。
1958年，Speranza等首次发现环氧化合物和异氰酸酯在季铵盐为催化剂条件下可生成OX后，人们先后发现了可用于催化恶唑烷酮环生成的合适催化剂。这些催化剂包括(1)亲核胺和铵盐；其中，亲核胺包括烷基胺类，如三乙胺、三甲胺、苄基二甲胺(BDMA)、2,4,6-三(二甲氨基)苯酚(DMP-30，US4766158)；含氮杂环类催化剂，如，1,8-二氮杂二环[5,4,0]十一碳-7-烯(DBU，US 2013016865)；咪唑及其衍生物，如2-苯基咪唑，2-甲基咪唑，2-乙基-4-甲基咪唑和4,4’-亚甲基-双(2-乙基-5-甲基咪唑)(US 5112932)；其它杂环如二氮杂双环辛稀、六亚甲基四胺、吗啉、哌啶、4-N,N二甲氨基吡啶(DMAP)；季铵盐类，如氯化三乙铵，氯化四乙铵，乙酸四乙铵，溴化四乙铵，氯化苄基三乙胺；(2)膦(US 3702839)，如三苯基膦、三甲基苯基磷、三乙基磷、乙酸三苯基膦、碘化三苯基膦、碘化乙基三苯基膦和溴化苄基三苯基膦；(3)Lewis酸/碱络合物，如AlCl3/HMPA3、AlCl3/OP(C6H4OCH3)3；(4)金属有机化合物，公开或已使用的有溴化锌(Sandler,J.Polymer Science A-1,5,1481,1967)；K.Gulbins发现氯化锂可催化芳香族异氰酸酯和环氧开环生成恶唑烷酮环(Chem.Ber.93,1875,1960)；R.R.Dileone发现正丁基锂具有催化恶唑烷酮环生成的活性(J.Polymer Science,Part A-1,Vol.8,p.609,1907)；J.E.Herweh和W.J.Kauffmand则报道了溴化锂的催化性能(Tetrahedron Leters,No.12,p,809,1971)；US 3817938公开了元素周期表中ⅡA、ⅢA族元素的烷氧基-或者苯氧基化合物催化剂；US 4066628公开的二烷基锌、羧酸锌、有机锌螯合化合物、三烷基铝；US 005238016公开的新型催化剂卤化锌；US 4658007公开了原位生成的有机碘化锑+5催化剂可催化恶唑烷酮环的生成。在最新的研究中，S.Tanimori等发现了新型催化剂[Pd(η3-C3H5)Cl]2可催化恶唑烷酮环的生成，但其反应物不是异氰酸酯与环氧之间的反应(Tetrahedron Leters,Vol.41,p.6785,2000)；F.Marjorie等研究了新型三氟甲磺酸镱(Yb(OTf)3)催化异氰酸酯和环氧的反应(Thermochimica Acta,Vol.543,p.188,2012)。这些催化剂催化异氰酸酯和环氧反应生成IS和OX时，通常需要较高的温度或者较长的时间，而关于Cr+3作为催化剂催化IS/OX的生成未见文献报道，本发明涉及的Cr+3催化剂是一种制备异氰脲酸酯和恶唑烷酮的高效催化剂。
值得注意的是，Cr+3类化合物应与有毒性的Cr+6化合物区分开来，因为前者在民业、工业上应用广泛，如在药店和保健食品商店出售的吡啶羧酸铬，是一种维他命添加剂；Cr+3在石油工业上有大量的应用也是基于其环境友好性。
专利US 6359147揭示了羧酸铬Cr+3催化剂催化开环的相关反应，如氮杂环丙烷，氧杂环丁烷，环氧乙烷分别与羧酸，酸酐，酰亚胺，内酯和碳酸酯的反应；以及含羟基化合物与酸酐，内酯，和碳酸酯的反应，环硫乙烷与酸酐的反应。但是，未提到该催化剂催化异氰酸酯三聚以及异氰酸酯与环氧的反应。
发明内容
本发明涉及使用三价铬催化剂(Cr+3)，优选羧酸铬，在有机碱助催化剂协同作用下，催化异氰酸酯三聚形成异氰脲酸酯，催化异氰酸酯与环氧形成恶唑烷酮的反应。通过控制催化剂浓度、助催化剂的量、反应温度、反应时间以及原料配比，得到含异氰脲酸酯/恶唑烷酮的端环氧低聚物，含异氰脲酸酯/恶唑烷酮的端异氰酸酯低聚物，以及含异氰脲酸酯/恶唑烷酮的高聚物等结构性能可控的聚合物材料，其中异氰脲酸酯/恶唑烷酮的质量比为0：100～100：0。
所述的Cr+3羧酸盐，主要为C3-C60，直链的或支链，芳基，烷基或者芳烷基的羧酸盐。其中，芳基是指含6～20个C的芳香烃，优选含单芳基的6～16个C取代基，如苯基；或者含两个或多个共轭环，如萘基；或者被单键相连的两个或多个芳基，如联苯；其中，芳基可以分别含少量支化或者支链烷基，含3～13个C的环烷基，氟基，氯基，溴基，三聚甲烷基，氰基，或者二氟甲氧基等取代基。其中优选己酸铬，戊酸铬，2-乙基己酸铬，油酸铬，硬脂酸铬，甲苯苯甲酸铬，甲酚铬，苯甲酸铬，烷基苯甲酸铬，烷氧基苯甲酸铬，环烷酸铬，烷氧基铬，醋酸铬，丁酸铬，丙酸铬，辛酸铬和癸酸铬。其中更优选，C3-C10，直链或支链，烷基，芳基或芳烷基的羧酸盐，如醋酸铬，丁酸铬，丙酸铬，苯甲酸铬，辛酸铬或癸酸铬。优选辛酸铬，支链或直链的C8，或者为两者的混合物，如2-乙基己酸铬或正辛酸铬。
所述的辛酸铬可以为其纯的化合物或者其在溶剂或稀释剂中的溶液，如邻苯二甲酸酯类或高沸点石油馏分。其中，Cr+3的浓度可以为0.5％至其在化合物中的浓度，如辛酸铬的10.8％，其中优选4％～8％。在反应体系中，以质量百分比计，Cr+3催化剂的浓度为0.01％～5％，其中优选0.02％～1％。
所述的助催化剂为有机碱类助催化剂，包括N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺(DMAC)、吡啶、4-甲基咪唑、2-甲基咪唑、4-乙基二甲基咪唑、二甲氨基吡啶(DMAP)、DBU、NEt3等有机碱，其中优选DMF、DMAC、吡啶、4-甲基咪唑、DMAP、DBU。在催化体系中，以质量百分比计，助催化剂的用量为Cr+3催化剂的0.01～20倍，其中优选0.5～10倍。
所述的异氰酸酯为分子结构中包含一个或多个异氰酸酯根(-NCO)且通常用于制备氨基甲酸酯的一类化合物，包括芳香族异氰酸酯、脂肪族或脂环族异氰酸酯及其衍生物的一种或几种的混合物。芳香族异氰酸酯，如2,4-甲苯二异氰酸酯(2,4-TDI)，2,6-甲苯二异氰酸酯(2,6-TDI)，4,4’-二苯基甲烷二异氰酸酯(MDI)，连甲氧基苯胺二异氰酸酯，甲苯胺二异氰酸酯，间苯二甲基异氰酸酯，1,5-萘二异氰酸酯(NDI)，对苯二异氰酸酯(PPDI)，1,4-二乙基苯-β,β'-二异氰酸酯；脂肪族异氰酸酯，如HDI(六亚甲基二异氰酸酯)，IPDI(异佛尔酮二异氰酸酯)，4,4’-亚甲基二(环己烷二异氰酸酯)等；异氰酸酯的衍生物包括聚合的和改性的异氰酸酯，可以是双官能度或高官能度异氰酸酯。
所述的异氰酸酯可以为上述异氰酸酯的改性产物，如含少量(<15％)2,4’-异构体的二苯基甲烷二异氰酸酯；二苯基甲烷二异氰酸酯或者含少量2,4’-异构体的二苯基甲烷二异氰酸酯混合物在催化剂作用下生成的聚合异氰酸酯。除此之外，聚合异氰酸酯还可包含亚甲基相连的多苯基多异氰酸酯与二苯基甲烷二异氰酸酯的混合物。多苯基多异氰酸酯的结构式如下图所示：
其中：n为0～10的整数。
所述的异氰酸酯，其中优选2,4-甲苯二异氰酸酯及其异构体，或者二者的混合物；4,4’-二苯基甲烷二异氰酸酯及其异构体，或者二者的混合物。
所述的异氰脲酸酯为含异氰酸根化合物三聚反应而成，其典型反应方程式及结构如下图所示：
其中，R表示芳基，脂肪族，脂环族，芳烷烃二价基团，n为数均聚合度，为1～4。
所述的环氧为结构中含一个或多个如下结构环氧基团的化合物，
其中，R是包括饱和的或不饱和烷烃，芳香族，或者脂环族、卤代基团，n为1～5的整数。优选环氧丙烷、环氧氯丙烷、2,2-二(2-羟苯基)丙烷缩水甘油醚(双酚A型)，2,2-二(3,5-二溴-4-羟苯基)丙烷缩水甘油醚(通常为四溴双酚A)，或者多种环氧的混合物；更优选环氧氯丙烷，双酚A型环氧树脂。
所述的恶唑烷酮环为含环氧基化合物与含异氰酸根化合物聚合而成，其典型反应方程式及结构如下图所示：
其中，m,n分别为异氰酸根和环氧基的摩尔数，当m：n>2时，得到含IS/OX的端异氰酸酯低聚物；当m：n<0.5时，得到含IS/OX的端环氧低聚物；当0.5<m：n<2时，得到含IS/OX的高聚物。其中，IS/OX的质量比为0：100～100：0。
其中，催化反应时所需的温度为50～200℃，优选50～150℃；催化反应时所需的时间为0～72h，优选2～24h。
附图说明
图1是实例2中含IS/OX的端环氧低聚物的红外谱图；图2是实例3中含IS/OX的端环氧产物的红外谱图；图3是实例4中含IS/OX的端异氰酸酯基低聚物的红外谱图；图4是实例5中含IS/OX的高聚物的红外谱图。
具体实施方式
下面采用实例进一步说明本发明，并非对本发明的限制。
通过傅立叶变换红外(FT-IR)谱图证明IS，OX的生成及其相对强度，其中1705cm-1、1750cm-1处为IS环、OX环上羰基(C＝O)的特征振动吸收峰，1600cm-1为芳香族化合物苯环特征振动吸收峰，2800～3100cm-1为甲基亚甲基特征振动吸收峰，可做参比峰计算其他特征振动吸收峰相对强度的变化，异氰酸酯基(N＝C＝O)的特征吸收峰在2242～2274cm-1处；环氧基上醚键(C-O-C)的特征吸收峰在890～939cm-1处。
下面是对实例中用到的仪器及试剂说明：
Nicolet 5700型红外光谱仪，溴化钾压片，扫描32次，扫描范围400-4000cm-1，分辨率4cm-1。
双酚A型环氧树脂E54，环氧当量187g/eq，工业品，无锡树脂厂；
环氧氯丙烷，分析纯，上海凌峰化学试剂有限公司；
MDI-50(二苯基甲烷二异氰酸酯)，Mn＝250g/mol，工业品，亨斯曼聚氨酯(上海)有限公司；
Cr+3催化剂HYCATTM 3000S，试剂级，Dimension Technology Chemical Systems,Inc.；
DMF，分析纯，上海凌峰化学试剂有限公司；
二甲氨基吡啶(DMAP)，试剂级，上海凌峰化学试剂有限公司；
吡啶，分析纯，上海凌峰化学试剂有限公司；
4-甲基咪唑，分析纯，上海凌峰化学试剂有限公司；
DBU，分析纯，美国空气化工公司；
以上试剂均经脱水干燥处理。
实例1：含IS/OX的端环氧低聚物的合成
在通氮气、带机械搅拌和温度计的100ml烧瓶中，加入56.1g(3eq.)E54和12.5g(1eq.)MDI-50，油浴加热至50℃，搅拌均匀后加入0.2％的催化剂HYCATTM3000S和1％的DMF。继续将油浴升温，直到反应体系维持在100℃，每隔1h取样测FTIR，直到2242～2274cm-1处NCO特征峰消失。5h后得到含IS/OX的端环氧基低聚物，IS/OX相对强度为58.3:41.7。
实例2：含IS/OX的端环氧低聚物的合成
在通氮气、带机械搅拌和温度计的250ml烧瓶中，加入46.75g(2.5eq.)E54和12.5g(1eq.)MDI-50，油浴加热体系至50℃，搅拌均匀。0.1％的催化剂HYCATTM 3000S溶解于50gDMF，将催化剂溶液加入反应体系。继续将油浴升温，直到反应体系维持在115℃，每隔1h取样测FTIR，直到2242～2274cm-1处NCO特征峰消失，如附图1所示。3h后得到含IS/OX的端环氧低聚物，室温下为浅黄色粘稠液体，IS/OX相对强度45.6：54.4。
实例3：含IS/OX的端环氧低聚物的合成
在通氮气、带机械搅拌和温度计的250ml烧瓶中，加入46.75g(2.5eq.)E54和12.5g(1eq.)MDI-50，油浴加热体系至50℃，搅拌均匀。0.1％的催化剂HYCATTM 3000S溶解于50gDMF，将催化剂溶液加入反应体系。继续将油浴升温，直到反应体系维持在130℃，每隔1h取样测FTIR，直到2242～2274cm-1处NCO特征峰消失，如附图2所示。2h后得到含IS/OX的端环氧根预聚体，室温下为浅黄色粘稠液体，IS/OX相对强度41.1:58.9。
实例4：含IS/OX的端异氰酸酯基低聚物的合成
在通氮气、带机械搅拌和温度计的250ml烧瓶中，加入18.7g(1eq.)E54和31.2g(2.5eq.)MDI-50，油浴加热体系至50℃，搅拌均匀。0.1％的催化剂HYCATTM 3000S溶解于50gDMF，将催化剂溶液加入反应体系。继续将油浴升温，直到反应体系维持在120℃，每隔1h取样测FTIR，直到890～939cm-1处环氧基上醚键(C-O-C)的特征吸收峰消失。4h后得到含IS/OX的端异氰酸酯基低聚物，室温下为浅黄色粘稠液体，IS/OX相对强度67.8:32.2，如附图3所示。
实例5：含IS/OX高聚物的合成
在通氮气、带机械搅拌和温度计的250ml烧瓶中，加入18.7g(1eq.)E54和12.5g(1eq.)MDI-50，油浴加热体系至50℃，搅拌均匀后，加入0.1％溶解于2g的DMF，继续将油浴升温，直到反应体系维持在100℃，每隔1h取样测FTIR，观测体系粘度变化，当粘度增至10000cp左右时，将反应物移至四氟板上浇片固化，跟踪2242～2274cm-1处NCO特征峰变化，直到特征振动峰消失。24h后得到含IS/OX的高聚物，室温下为棕色固体，IS/OX相对强度为48.5:51.5，如附图4所示。
实例6-8：助催化剂(DMF)对MDI-100/环氧氯丙烷反应的催化效应
在通氮气、磁力搅拌的100ml单口烧瓶中，加入20.4g(2.2eq.)环氧氯丙烷和25g(1eq.)MDI-100，加入催化剂，催化剂种类及用量见表1所示。油浴加热反应物料至60℃，搅拌均匀后保持2h，然后将油浴升温至80℃维持2h，最后升温至100℃维持13h，每隔1h取样测FTIR，观测体系粘度状态变化。FTIR谱图中取2920cm-1处甲基亚甲基特征振动吸收峰的峰高作内标参比，计算其它特征振动峰的相对强度，2270cm-1处为NCO的特征振动峰，结果如表1所示。
表1不同催化体系对MDI-100/环氧氯丙烷反应的催化效应
a hycat3000s催化剂用量为反应物总量的0.1％，DMF为0.5％；
b OX,IS特征振动吸收峰分别位于1755cm-1，1710cm-1处；
实例9-14：助催化剂(DMF)对其它异氰酸酯与环氧氯丙烷反应的催化效应
在通氮气、磁力搅拌的100ml单口烧瓶中，加入20.4g(2.2eq.)环氧氯丙烷和相应的异氰酸酯，以及催化剂，催化剂和异氰酸酯种类及用量见表2所示。油浴加热物料体系至60℃，搅拌均匀后保持2h，然后将油浴升温至80℃维持2h，最后升温至100℃维持13h，每隔1h取样测FTIR，观测体系粘度状态变化。在FTIR谱图中取2800cm-1～3100cm-1处甲基亚甲基特征振动吸收峰作内标参比，计算其它特征振动峰相对强度，结果如表2、3、4所示。
表2助催化DMF对TDI与环氧氯丙烷反应的催化效应
ahycat3000s催化剂用量为反应物总量的0.1％，DMF为1％；
bOX,IS特征振动吸收峰分别位于1755cm-1，1710cm-1处；
表3助催化DMF对HDI与环氧氯丙烷反应的催化效应
a hycat3000s催化剂用量为反应物总量的0.1％，DMF为1％；
b OX,IS特征振动峰分别位于1722cm-1，1689cm-1处，参比峰为2940cm-1处振动峰
表4助催化DMF对IPDI与环氧氯丙烷反应的催化效应
a hycat3000s催化剂用量为反应物总量的0.1％，DMF为1％；
b OX,IS特征振动吸收峰分别位于1765cm-1,1690cm-1处,参比峰为2956cm-1处振动峰；
实例15-16:不同助催化剂催化异氰酸酯自聚反应
在通氮气、磁力搅拌的100ml单口烧瓶中，加入15g异氰酸酯，有机碱种类及用量见表2所示。油浴加热物料至70℃，搅拌均匀后保持1h，观察现象；随后，将适量的hycat3000s加入反应体系，观测体系粘度状态变化，并取样测FT-IR。FTIR谱图中取1600cm-1处苯环特征振动吸收峰的峰高作内标参比，计算其它特征振动峰的相对强度，结果如表5,6所示。
表5不同助催化对MDI-100自聚反应的催化效应
a.hycat3000s为原料的0.1％，有机碱的用量为0.6％；
b.IS特征振动吸收峰分别位于1700cm-1；
表6不同催化体系对HDI自聚反应的催化效应
a.有机碱的用量为3％。
Claims (9)
1.一种Cr3+的羧酸盐催化剂在有机碱助催化剂的作用下，催化异氰酸酯三聚形成异氰脲酸酯，催化异氰酸酯与环氧化合物反应生成噁唑烷酮的反应的用途，其中，Cr3+的浓度为0.5％至其在化合物中的浓度，催化剂用量为反应物的0.01～5wt％，反应温度为50～200℃，反应时间大于0且小于等于72h。
2.根据权利要求1所述的Cr3+的羧酸盐催化剂的用途，其特征为C3-C60、直链的或支链的、芳基的、烷基的或者芳烷基的羧酸盐。
3.根据权利要求1所述的Cr3+的羧酸盐催化剂的用途，包括如下化合物的一种或几种的混合物，己酸铬，戊酸铬，2-乙基己酸铬，油酸铬，硬脂酸铬，甲苯苯甲酸铬，苯甲酸铬，烷基苯甲酸铬，烷氧基苯甲酸铬，环烷酸铬，醋酸铬，丁酸铬，丙酸铬，辛酸铬和癸酸铬。
4.根据权利要求1所述的Cr3+的羧酸盐催化剂的用途，其中助催化剂包括如下化合物中的一种或几种的混合物，N,N-二甲基甲酰胺(DMF)、N,N-二甲基乙酰胺(DMAC)、吡啶、4-甲基咪唑、2-甲基咪唑、4-乙基二甲基咪唑、二甲氨基吡啶(DMAP)、DBU、NEt3。
5.根据权利要求1所述的Cr3+的羧酸盐催化剂的用途，其中助催化剂的用量为Cr3+羧酸盐催化剂的0.01～20倍，以质量计。
6.根据权利要求1所述的Cr3+的羧酸盐催化剂的用途，其特征在于通过控制催化剂浓度、反应温度、反应时间以及原料配比，得到含异氰脲酸酯/噁唑烷酮的端环氧基低聚物，含异氰脲酸酯/噁唑烷酮的端异氰酸酯基低聚物，以及含异氰脲酸酯/噁唑烷酮的高聚物的结构性能可控的材料，结构中的异氰脲酸酯/噁唑烷酮的质量比为0：100～100：0(wt/wt)。
7.根据权利要求6所述的Cr3+的羧酸盐催化剂的用途，其中异氰酸酯为分子结构中包含一个或多个异氰酸酯根(-NCO)且通常用于制备氨基甲酸酯的一类化合物，包括芳香族异氰酸酯、脂肪族或脂环族异氰酸酯及其衍生物的一种或几种的混合物。
8.根据权利要求6所述的Cr3+的羧酸盐催化剂的用途，其中环氧化合物为结构中含一个或多个如下环氧结构的化合物，
其中，R是包括饱和的烷烃或不饱和烷烃，芳香族、脂环族、卤代基团，n为1～5的整数。
9.根据权利要求6所述的Cr3+的羧酸盐催化剂的用途，其中异氰脲酸酯为含异氰酸酯基化合物三聚反应而成，其典型反应方程式及结构如下图所示：
其中，R表示芳基、脂肪族、脂环族、芳烷烃二价基团，n为数均聚合度，为1～4，
所述的噁唑烷酮为含环氧基化合物与含异氰酸酯基化合物开环聚合而成；当异氰酸酯基与环氧基的摩尔数之比大于2时，得到含异氰脲酸酯/噁唑烷酮的端异氰酸酯基低聚物；当异氰酸酯基与环氧基的摩尔数之比小于0.5时，得到含异氰脲酸酯/噁唑烷酮的端环氧基低聚物；当异氰酸酯基与环氧基的摩尔数之比小于2且大于0.5时，得到含异氰脲酸酯/噁唑烷酮的高聚物。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410082417.7A CN104163906B (zh) | 2014-03-07 | 2014-03-07 | 一种用于异氰酸酯三聚，异氰酸酯与环氧成环反应的催化剂及其应用 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410082417.7A CN104163906B (zh) | 2014-03-07 | 2014-03-07 | 一种用于异氰酸酯三聚，异氰酸酯与环氧成环反应的催化剂及其应用 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104163906A CN104163906A (zh) | 2014-11-26 |
| CN104163906B true CN104163906B (zh) | 2018-01-05 |
Family
ID=51907901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410082417.7A Expired - Fee Related CN104163906B (zh) | 2014-03-07 | 2014-03-07 | 一种用于异氰酸酯三聚，异氰酸酯与环氧成环反应的催化剂及其应用 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104163906B (zh) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2018531894A (ja) * | 2015-08-17 | 2018-11-01 | コベストロ、ドイチュラント、アクチエンゲゼルシャフトＣｏｖｅｓｔｒｏ Ｄｅｕｔｓｃｈｌａｎｄ Ａｇ | 環状アンモニウム塩を触媒として使用してイソシアネートを変性する方法 |
| EP3596147B1 (de) * | 2017-03-17 | 2021-12-08 | Basf Se | Verfahren zur herstellung von oxazolidinongruppen aufweisenden verbindungen |
| CN113512386A (zh) * | 2021-03-16 | 2021-10-19 | 山东光实能源有限公司 | 一种用于太阳能发电路面的环氧树脂基复合粘结材料 |
| CN113200932B (zh) * | 2021-05-07 | 2023-03-24 | 南京工业大学 | 一种恶唑烷酮的合成方法 |
| CN113637388A (zh) * | 2021-08-20 | 2021-11-12 | 国网福建省电力有限公司电力科学研究院 | 一种异氰酸酯基环氧树脂防锈底漆 |
| CN116606623B (zh) * | 2023-07-18 | 2023-09-08 | 广东星印包装材料有限公司 | 聚氨酯胶黏剂的制备方法、聚氨酯胶黏剂及其在耐高温蒸煮包装膜生产中的应用 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013089962A1 (en) * | 2011-12-12 | 2013-06-20 | Chevron Phillips Chemical Company Lp | Preparation of an olefin oligomerization catalyst |
| CN1946657B (zh) * | 2004-02-20 | 2013-09-18 | 切夫里昂菲利普化学有限责任公司 | 制备烯烃低聚合催化剂的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998056500A1 (en) * | 1997-06-13 | 1998-12-17 | Dimension Technology Chemical Systems, Inc. | Use of chromium (iii) carboxylates as a catalyst |
| CN1238345C (zh) * | 2004-02-26 | 2006-01-25 | 湖南大学 | 三(甲基)丙烯酸环氧酯基异氰尿酸酯及其合成方法 |
| CN101254474B (zh) * | 2008-03-19 | 2010-06-02 | 安徽师范大学 | 用于异氰酸酯三聚的催化剂及其制备、使用方法 |
| CN102604384B (zh) * | 2012-02-29 | 2013-06-19 | 苏州巨峰电气绝缘系统股份有限公司 | 一种耐冷媒的高低压电机通用无溶剂浸渍树脂及其制备方法 |
-
2014
- 2014-03-07 CN CN201410082417.7A patent/CN104163906B/zh not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1946657B (zh) * | 2004-02-20 | 2013-09-18 | 切夫里昂菲利普化学有限责任公司 | 制备烯烃低聚合催化剂的方法 |
| WO2013089962A1 (en) * | 2011-12-12 | 2013-06-20 | Chevron Phillips Chemical Company Lp | Preparation of an olefin oligomerization catalyst |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104163906A (zh) | 2014-11-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104163906B (zh) | 一种用于异氰酸酯三聚，异氰酸酯与环氧成环反应的催化剂及其应用 | |
| KR102327859B1 (ko) | 촉매로서 스피로시클릭 암모늄 염을 사용하는 이소시아네이트 개질 방법 | |
| JP6581272B2 (ja) | ポリイソシアネート硬化物、及びポリイソシアネート硬化物の製造方法 | |
| US20140378648A1 (en) | Method for preparing a compound comprising at least one beta-hydroxy-urethane unit and/or at least one upsilon-hydroxy-urethane unit | |
| KR101200197B1 (ko) | 카르보디이미드 개질된 유기 이소시아네이트의 개선된 제조방법 | |
| Hu et al. | Synthesis and structure investigation of hexamethylene diisocyanate (HDI)-based polyisocyanates | |
| CA2854689C (en) | Curable polyisocyanate composition comprising an epoxy resin | |
| CN107922563A (zh) | 使用环状铵盐作为催化剂改性异氰酸酯的方法 | |
| CN103987750A (zh) | 制备多异氰酸酯的方法及其应用 | |
| KR20190118580A (ko) | 촉매로서 스피로고리형 암모늄 염에 의해 적어도 펜타메틸렌 디이소시아네이트를 개질하는 방법 | |
| Guo et al. | Catalysts for isocyanate cyclotrimerization | |
| BR112015014403B1 (pt) | 2-oxo-1,3-dioxolano-4-carboxamida e processo para a preparação de um 2-oxo-1, 3- dioxolano-4-carboxamida | |
| CN105980393A (zh) | 使用具有n-p-n序列的催化剂进行异氰酸酯改性的方法 | |
| JP2022536666A (ja) | エポキシ基末端ポリオキサゾリジノンを製造する方法 | |
| CN105408383A (zh) | 用于制备多异氰酸酯的方法和所述多异氰酸酯的用途 | |
| JP5597352B2 (ja) | ウレトジオンポリイソシアネートの製造 | |
| EP3194461B1 (en) | A curable organic polymer comprising at least one acylurea unit, its preparation and use | |
| JP6174687B2 (ja) | 新規なカルボジイミド含有組成物、その合成方法、及びその使用 | |
| US20160046756A1 (en) | Process for preparing polyisocyanates and catalyst kit therefor | |
| Wu et al. | Fast cyclotrimerization of a wide range of isocyanates to isocyanurates over acid/base conjugates under bulk conditions | |
| EP3700956B1 (en) | Catalysts for making oxazolidinone materials | |
| CN1832975A (zh) | 用于异氰酸酯选择性二聚的新颖催化剂 | |
| WO2020166646A1 (ja) | ポリイソシアヌレート原料組成物、及びポリイソシアヌレートの製造方法 | |
| Hu et al. | Catalytic selectivity and process optimization of the trimerization of toluene diisocyanate | |
| PL230456B1 (pl) | Sposób otrzymywania bezizocyjanianowych polihydroksyuretanów oraz bezizocyjanianowych polihydroksyuretano-epoksydów |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180105 Termination date: 20200307 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |