JP2015512989A - ポリイソシアネート三量化触媒組成物 - Google Patents
ポリイソシアネート三量化触媒組成物 Download PDFInfo
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- JP2015512989A JP2015512989A JP2015502188A JP2015502188A JP2015512989A JP 2015512989 A JP2015512989 A JP 2015512989A JP 2015502188 A JP2015502188 A JP 2015502188A JP 2015502188 A JP2015502188 A JP 2015502188A JP 2015512989 A JP2015512989 A JP 2015512989A
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- Prior art keywords
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- composition
- compound
- polyisocyanate
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- 239000000203 mixture Substances 0.000 title claims abstract description 329
- 239000005056 polyisocyanate Substances 0.000 title claims abstract description 200
- 229920001228 polyisocyanate Polymers 0.000 title claims abstract description 200
- 239000003054 catalyst Substances 0.000 title claims abstract description 130
- 238000005829 trimerization reaction Methods 0.000 title claims abstract description 86
- 150000001875 compounds Chemical class 0.000 claims abstract description 195
- 229920005862 polyol Polymers 0.000 claims abstract description 60
- 150000003077 polyols Chemical class 0.000 claims abstract description 56
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 claims abstract description 30
- -1 alkali metal salt Chemical class 0.000 claims abstract description 29
- 229920000582 polyisocyanurate Polymers 0.000 claims abstract description 29
- 239000011495 polyisocyanurate Substances 0.000 claims abstract description 29
- 239000000463 material Substances 0.000 claims abstract description 27
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 21
- 239000003822 epoxy resin Substances 0.000 claims abstract description 20
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 35
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 31
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000012948 isocyanate Substances 0.000 claims description 28
- 150000002513 isocyanates Chemical class 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000007795 chemical reaction product Substances 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 21
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 21
- 125000001033 ether group Chemical group 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 17
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 229920005906 polyester polyol Polymers 0.000 claims description 16
- 229920000570 polyether Polymers 0.000 claims description 16
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000007942 carboxylates Chemical group 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 235000011056 potassium acetate Nutrition 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 5
- 150000004703 alkoxides Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 4
- 239000004300 potassium benzoate Substances 0.000 claims description 4
- 235000010235 potassium benzoate Nutrition 0.000 claims description 4
- 229940103091 potassium benzoate Drugs 0.000 claims description 4
- 239000001747 Potassium fumarate Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 claims description 3
- SHPKCSFVQGSAJU-SEPHDYHBSA-L potassium fumarate Chemical compound [K+].[K+].[O-]C(=O)\C=C\C([O-])=O SHPKCSFVQGSAJU-SEPHDYHBSA-L 0.000 claims description 3
- 235000019295 potassium fumarate Nutrition 0.000 claims description 3
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 3
- 239000001521 potassium lactate Substances 0.000 claims description 3
- 235000011085 potassium lactate Nutrition 0.000 claims description 3
- 229960001304 potassium lactate Drugs 0.000 claims description 3
- BLGUIMKBRCQORR-UHFFFAOYSA-M potassium;hexanoate Chemical compound [K+].CCCCCC([O-])=O BLGUIMKBRCQORR-UHFFFAOYSA-M 0.000 claims description 3
- RLEFZEWKMQQZOA-UHFFFAOYSA-M potassium;octanoate Chemical compound [K+].CCCCCCCC([O-])=O RLEFZEWKMQQZOA-UHFFFAOYSA-M 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000001744 Sodium fumarate Substances 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- MSJMDZAOKORVFC-SEPHDYHBSA-L disodium fumarate Chemical compound [Na+].[Na+].[O-]C(=O)\C=C\C([O-])=O MSJMDZAOKORVFC-SEPHDYHBSA-L 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 229940005573 sodium fumarate Drugs 0.000 claims description 2
- 235000019294 sodium fumarate Nutrition 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 235000011054 acetic acid Nutrition 0.000 claims 1
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
- PGYPOBZJRVSMDS-UHFFFAOYSA-N loperamide hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C=1C=CC=CC=1)(C(=O)N(C)C)CCN(CC1)CCC1(O)C1=CC=C(Cl)C=C1 PGYPOBZJRVSMDS-UHFFFAOYSA-N 0.000 description 24
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
- 150000003857 carboxamides Chemical class 0.000 description 20
- 239000002904 solvent Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 235000013877 carbamide Nutrition 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 150000007945 N-acyl ureas Chemical group 0.000 description 11
- 239000004202 carbamide Substances 0.000 description 11
- 230000008569 process Effects 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000004814 polyurethane Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 229920003319 Araldite® Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000002015 acyclic group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- 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 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
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- 238000010791 quenching Methods 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229960004249 sodium acetate Drugs 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PAUHLEIGHAUFAK-UHFFFAOYSA-N 1-isocyanato-1-[(1-isocyanatocyclohexyl)methyl]cyclohexane Chemical compound C1CCCCC1(N=C=O)CC1(N=C=O)CCCCC1 PAUHLEIGHAUFAK-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- DAXRGSDCXVUHEW-UHFFFAOYSA-N 2-(benzhydrylamino)ethanol Chemical compound C=1C=CC=CC=1C(NCCO)C1=CC=CC=C1 DAXRGSDCXVUHEW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4829—Polyethers containing at least three hydroxy 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
- C08G18/09—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
-
- 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
-
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| EP12162154.4A EP2644270A1 (en) | 2012-03-29 | 2012-03-29 | Polyisocyanate trimerization catalyst composition |
| EP12162154.4 | 2012-03-29 | ||
| PCT/EP2013/055014 WO2013143841A1 (en) | 2012-03-29 | 2013-03-12 | Polyisocyanate trimerization catalyst composition |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015528039A (ja) * | 2012-07-17 | 2015-09-24 | ハンツマン・インターナショナル・エルエルシー | 中間体ポリイソシアヌレート含有材料 |
| JP2016521770A (ja) * | 2013-05-24 | 2016-07-25 | ハンツマン・インターナショナル・エルエルシー | 硬化性ポリイソシアネート組成物の製造に適したアルデヒド含有化合物 |
| JP2022513473A (ja) * | 2018-12-11 | 2022-02-08 | トリマー テクノロジーズ エルエルシー | ポリイソシアヌレート系ポリマー及び繊維強化複合材料 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11292868B2 (en) | 2013-11-29 | 2022-04-05 | Basf Se | Polyurethane system with long pot life and rapid hardening |
| WO2016188774A1 (en) | 2015-05-27 | 2016-12-01 | Basf Se | Use of a composition for stabilizing a geological formation in oil fields, gas fields, water pumping fields, mining or tunnel constructions |
| BR112017025340B1 (pt) | 2015-05-28 | 2021-12-28 | Basf Se | Processo para a preparação de compostos de poliuretano-poliisocianurato, composto de poliuretano-poliisocianurato e uso de um composto de poliuretano-poliisocianurato |
| CN107683297B (zh) * | 2015-05-29 | 2020-09-08 | 巴斯夫欧洲公司 | 用于纤维复合材料的具有较长开放时间的聚氨酯-聚异氰脲酸酯树脂 |
| CN108368284B (zh) * | 2015-12-18 | 2021-07-13 | Sika技术股份公司 | 用于低温固化的可热膨胀泡沫 |
| EP3458491A1 (en) * | 2016-05-18 | 2019-03-27 | Basf Se | Process for preparing polyisocyanurate rigid foams |
| DK3515958T3 (da) * | 2016-09-20 | 2020-09-14 | Covestro Deutschland Ag | Anisotrope kompositmaterialer baseret på polyisocyanater |
| EP3381962A1 (de) * | 2017-03-29 | 2018-10-03 | Covestro Deutschland AG | Erzeugung von polyisocyanuratschichten durch getrennte auftragung von isocyanatkomponenten und katalysatoren |
| CN108730753B (zh) * | 2017-04-14 | 2020-07-07 | 江苏先诺新材料科技有限公司 | 一种聚酰亚胺纤维复合材料气瓶及其制备方法和应用 |
| EP3864063B1 (en) | 2018-10-09 | 2023-11-29 | Basf Se | A process for preparing a prepreg binder composition, a prepreg and use thereof |
| WO2020165135A1 (en) | 2019-02-11 | 2020-08-20 | Basf Se | Acrylic copolymer capsule designed to open up at < 90°c for controlled release of in-situ forming pu/pir catalyst |
| KR20220049564A (ko) | 2019-08-19 | 2022-04-21 | 바스프 에스이 | 기계적 성질이 우수한 폴리우레탄-폴리이소시아누레이트 화합물 |
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| JPH0395213A (ja) * | 1989-05-11 | 1991-04-19 | Teijin Ltd | 複合系硬化性液状樹脂組成物 |
| US5288899A (en) * | 1993-06-30 | 1994-02-22 | Miles Inc. | Liquification of diphenylmethane diisocyanate by partially reacting the isocyanate groups with blocking agents |
| JPH06199987A (ja) * | 1992-11-13 | 1994-07-19 | Nippon Polyurethane Ind Co Ltd | ポリイソシアネート硬化剤、並びにこれを用いたポリウレタン塗料組成物およびポリウレタン接着剤組成物 |
| US6127308A (en) * | 1997-12-31 | 2000-10-03 | Bayer Corporation | Trimer catalyst system for aliphatic and aromatic isocyanates |
| JP2006283025A (ja) * | 2005-03-31 | 2006-10-19 | Bayer Material Science Llc | 低表面エネルギーポリイソシアネート、その製造方法およびそれを含む一または二成分被覆組成物 |
| WO2008060454A2 (en) * | 2006-11-14 | 2008-05-22 | Bayer Materialscience Llc | Amide/urea-modified liquid diphenylmethane diisocyanates |
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| DE1230778B (de) | 1965-05-24 | 1966-12-22 | Bayer Ag | Verfahren zur Herstellung von acylierten Harnstoffpolyisocyanaten |
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- 2013-03-12 WO PCT/EP2013/055014 patent/WO2013143841A1/en not_active Ceased
- 2013-03-12 CN CN201380016760.5A patent/CN104394985A/zh active Pending
- 2013-03-12 CN CN201811358609.0A patent/CN109553739A/zh active Pending
- 2013-03-12 RU RU2014143488A patent/RU2628084C2/ru active
- 2013-03-12 MX MX2014011587A patent/MX370889B/es active IP Right Grant
- 2013-03-12 EP EP13708493.5A patent/EP2830761B1/en active Active
- 2013-03-12 CA CA2866990A patent/CA2866990C/en active Active
- 2013-03-12 KR KR1020147029847A patent/KR20140143411A/ko not_active Ceased
- 2013-03-12 US US14/382,020 patent/US20150031527A1/en not_active Abandoned
- 2013-03-12 IN IN7402DEN2014 patent/IN2014DN07402A/en unknown
- 2013-03-12 BR BR112014023105-2A patent/BR112014023105B1/pt not_active IP Right Cessation
- 2013-03-22 TW TW102110385A patent/TWI491446B/zh not_active IP Right Cessation
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015528039A (ja) * | 2012-07-17 | 2015-09-24 | ハンツマン・インターナショナル・エルエルシー | 中間体ポリイソシアヌレート含有材料 |
| JP2016521770A (ja) * | 2013-05-24 | 2016-07-25 | ハンツマン・インターナショナル・エルエルシー | 硬化性ポリイソシアネート組成物の製造に適したアルデヒド含有化合物 |
| JP2022513473A (ja) * | 2018-12-11 | 2022-02-08 | トリマー テクノロジーズ エルエルシー | ポリイソシアヌレート系ポリマー及び繊維強化複合材料 |
| JP7671986B2 (ja) | 2018-12-11 | 2025-05-07 | トリマー テクノロジーズ エルエルシー | ポリイソシアヌレート系ポリマー及び繊維強化複合材料 |
Also Published As
| Publication number | Publication date |
|---|---|
| RU2014143488A (ru) | 2016-05-20 |
| TW201343252A (zh) | 2013-11-01 |
| US20220134322A1 (en) | 2022-05-05 |
| CN109553739A (zh) | 2019-04-02 |
| RU2628084C2 (ru) | 2017-08-14 |
| US20150031527A1 (en) | 2015-01-29 |
| WO2013143841A1 (en) | 2013-10-03 |
| CN104394985A (zh) | 2015-03-04 |
| CA2866990C (en) | 2016-06-07 |
| EP2644270A1 (en) | 2013-10-02 |
| KR20140143411A (ko) | 2014-12-16 |
| EP2830761A1 (en) | 2015-02-04 |
| EP2830761B1 (en) | 2020-08-12 |
| MX2014011587A (es) | 2014-11-21 |
| CA2866990A1 (en) | 2013-10-03 |
| IN2014DN07402A (enExample) | 2015-04-24 |
| BR112014023105B1 (pt) | 2021-02-09 |
| TWI491446B (zh) | 2015-07-11 |
| MX370889B (es) | 2020-01-09 |
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