TW201404792A - 包含中間聚異三聚氰酸酯之材料 - Google Patents
包含中間聚異三聚氰酸酯之材料 Download PDFInfo
- Publication number
- TW201404792A TW201404792A TW102121226A TW102121226A TW201404792A TW 201404792 A TW201404792 A TW 201404792A TW 102121226 A TW102121226 A TW 102121226A TW 102121226 A TW102121226 A TW 102121226A TW 201404792 A TW201404792 A TW 201404792A
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- TW
- Taiwan
- Prior art keywords
- polyisocyanate
- composition
- group
- compound
- polyisocyanurate
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 118
- 229920000582 polyisocyanurate Polymers 0.000 title claims abstract description 75
- 239000011495 polyisocyanurate Substances 0.000 title claims abstract description 71
- 239000000203 mixture Substances 0.000 claims abstract description 162
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 153
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 153
- 238000000034 method Methods 0.000 claims abstract description 54
- 239000003054 catalyst Substances 0.000 claims description 104
- 150000001875 compounds Chemical class 0.000 claims description 94
- -1 polyarylamines Polymers 0.000 claims description 40
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 36
- 229920005862 polyol Polymers 0.000 claims description 26
- 239000002023 wood Substances 0.000 claims description 25
- 239000003822 epoxy resin Substances 0.000 claims description 24
- 229920000647 polyepoxide Polymers 0.000 claims description 24
- 150000003077 polyols Chemical class 0.000 claims description 23
- 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 21
- 239000012948 isocyanate Substances 0.000 claims description 19
- 150000002513 isocyanates Chemical class 0.000 claims description 19
- 239000004593 Epoxy Substances 0.000 claims description 17
- 239000000835 fiber Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 239000011324 bead Substances 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 11
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 10
- 150000007942 carboxylates Chemical class 0.000 claims description 10
- 239000004927 clay Substances 0.000 claims description 10
- 229910052570 clay Inorganic materials 0.000 claims description 10
- 239000011521 glass Substances 0.000 claims description 10
- 229920000570 polyether Polymers 0.000 claims description 10
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 10
- 239000002699 waste material Substances 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 150000004703 alkoxides Chemical class 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000011111 cardboard Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000013638 trimer Substances 0.000 claims description 6
- 244000198134 Agave sisalana Species 0.000 claims description 5
- 244000025254 Cannabis sativa Species 0.000 claims description 5
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims description 5
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims description 5
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 235000009120 camo Nutrition 0.000 claims description 5
- 239000004917 carbon fiber Substances 0.000 claims description 5
- 239000004568 cement Substances 0.000 claims description 5
- 235000005607 chanvre indien Nutrition 0.000 claims description 5
- 239000007799 cork Substances 0.000 claims description 5
- 229920001971 elastomer Polymers 0.000 claims description 5
- 239000010881 fly ash Substances 0.000 claims description 5
- 239000005338 frosted glass Substances 0.000 claims description 5
- 239000003365 glass fiber Substances 0.000 claims description 5
- 239000011487 hemp Substances 0.000 claims description 5
- 229910052809 inorganic oxide Inorganic materials 0.000 claims description 5
- 239000012764 mineral filler Substances 0.000 claims description 5
- 239000011490 mineral wool Substances 0.000 claims description 5
- 239000002105 nanoparticle Substances 0.000 claims description 5
- 239000004745 nonwoven fabric Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 235000011056 potassium acetate Nutrition 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- 239000005060 rubber Substances 0.000 claims description 5
- 239000004576 sand Substances 0.000 claims description 5
- 150000005846 sugar alcohols Polymers 0.000 claims description 5
- 229920002994 synthetic fiber Polymers 0.000 claims description 5
- 239000012209 synthetic fiber Substances 0.000 claims description 5
- 229920001169 thermoplastic Polymers 0.000 claims description 5
- 229920001187 thermosetting polymer Polymers 0.000 claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims description 5
- 229910052902 vermiculite Inorganic materials 0.000 claims description 5
- 235000019354 vermiculite Nutrition 0.000 claims description 5
- 239000010455 vermiculite Substances 0.000 claims description 5
- 239000002759 woven fabric Substances 0.000 claims description 5
- 241000208202 Linaceae Species 0.000 claims description 4
- 235000004431 Linum usitatissimum Nutrition 0.000 claims description 4
- 238000010276 construction Methods 0.000 claims description 4
- 239000002923 metal particle Substances 0.000 claims description 4
- 239000002557 mineral fiber Substances 0.000 claims description 4
- 239000000123 paper Substances 0.000 claims description 4
- 239000011087 paperboard Substances 0.000 claims description 4
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 4
- PHZLMBHDXVLRIX-UHFFFAOYSA-M potassium lactate Chemical compound [K+].CC(O)C([O-])=O PHZLMBHDXVLRIX-UHFFFAOYSA-M 0.000 claims description 4
- 239000001521 potassium lactate Substances 0.000 claims description 4
- 235000011085 potassium lactate Nutrition 0.000 claims description 4
- 229960001304 potassium lactate Drugs 0.000 claims description 4
- SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 claims description 3
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 3
- 239000004300 potassium benzoate Substances 0.000 claims description 3
- 235000010235 potassium benzoate Nutrition 0.000 claims description 3
- 229940103091 potassium benzoate 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
- 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 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 2
- 239000004280 Sodium formate Substances 0.000 claims description 2
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 claims description 2
- 239000001632 sodium acetate Substances 0.000 claims description 2
- 235000017281 sodium acetate Nutrition 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 2
- 235000019254 sodium formate Nutrition 0.000 claims description 2
- 239000004411 aluminium Substances 0.000 claims 2
- BWLKKFSDKDJGDZ-UHFFFAOYSA-N [isocyanato(phenyl)methyl]benzene Chemical compound C=1C=CC=CC=1C(N=C=O)C1=CC=CC=C1 BWLKKFSDKDJGDZ-UHFFFAOYSA-N 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 239000008187 granular material Substances 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 15
- 239000000543 intermediate Substances 0.000 description 62
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000004202 carbamide Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 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 12
- 238000002360 preparation method Methods 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 238000005829 trimerization reaction Methods 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000003197 catalytic effect Effects 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000003857 carboxamides Chemical class 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 229920005906 polyester polyol Polymers 0.000 description 5
- 229910052700 potassium Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 4
- 229920003319 Araldite® Polymers 0.000 description 4
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
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- 235000013772 propylene glycol Nutrition 0.000 description 4
- 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
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- 229910052736 halogen Inorganic materials 0.000 description 3
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- 239000011541 reaction mixture Substances 0.000 description 3
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FRPHFZCDPYBUAU-UHFFFAOYSA-N Bromocresolgreen Chemical compound CC1=C(Br)C(O)=C(Br)C=C1C1(C=2C(=C(Br)C(O)=C(Br)C=2)C)C2=CC=CC=C2S(=O)(=O)O1 FRPHFZCDPYBUAU-UHFFFAOYSA-N 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
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 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
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000002585 base Substances 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
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
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- 238000000227 grinding Methods 0.000 description 2
- 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 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
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- 239000012535 impurity Substances 0.000 description 2
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 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
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000003918 potentiometric titration Methods 0.000 description 2
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- 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
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- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
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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
- C08G18/08—Processes
- C08G18/16—Catalysts
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Abstract
本發明揭示一種穩定部分固化之聚異三聚氰酸酯組合物，該組合物含有聚異三聚氰酸酯(包含中間聚異三聚氰酸酯之材料)且其可進一步固化。另外揭示一種製造包含中間(部分固化)聚異三聚氰酸酯之材料的方法及一種進一步固化該部分固化之聚異三聚氰酸酯組合物的方法。亦揭示由包含部分固化之中間聚異三聚氰酸酯之材料製成或可藉由該材料獲得之包含聚異三聚氰酸酯之材料及進一步固化包含部分固化之聚異三聚氰酸酯之組合物(中間材料)之方法。
Description
本發明係關於一種穩定部分固化之聚異氰酸酯組合物，其包含聚異三聚氰酸酯(稱為包含中間聚異三聚氰酸酯之材料)且可進一步固化。
本發明進而有關於一種製造包含中間(部分固化)聚異三聚氰酸酯之材料的方法及一種進一步固化該部分固化之聚異三聚氰酸酯組合物的方法，其中使用根據本發明之三聚觸媒組合物。
本發明進而有關於一種由該包含部分固化之中間聚異三聚氰酸酯之材料製成或可藉由該材料獲得之包含聚異三聚氰酸酯之材料，及有關於進一步固化該包含部分固化之聚異三聚氰酸酯之組合物(中間材料)之方法。
本發明進而有關於一種根據本發明之三聚觸媒組合物可由聚異氰酸酯組合物開始製得包含「穩定」且「部分固化」中間聚異三聚氰酸酯之材料之用途。
WO2010023060揭示一種可固化組合物及藉由將包含多元醇、酸酐及三聚觸媒之異氰酸酯反應性混合物與聚異氰酸酯組合來形成聚異三聚氰酸酯之方法。該三聚觸媒係選自鹼金屬羧酸鹽、第四銨羧酸鹽及其混合物，該羧酸鹽具有1-12個碳原子。
於US 3970600中已描述含醯胺及/或醯脲基之異氰尿酸酯-聚異氰酸酯之穩定溶液。其等防止在含異氰尿酸酯基之聚異氰酸酯中沉積出微細或粗結晶固形物。首先聚異氰酸酯與多元羧酸反應製得具有醯胺及/或(經取代)醯脲基之聚異氰酸酯。接著該聚異氰酸酯經三聚化而形成異氰尿酸酯-聚異氰酸酯，然後添加酸來終止該轉化。
於JP 2-110123中，脂族二異氰酸酯經三聚化以製備具有異氰尿酸酯結構之聚異氰酸酯，在已達到期望的轉化程度時使用觸媒及減活化劑(換言之，減活化劑用為終止劑來終止三聚反應)。該減活化劑具有結構式-CO-NH2或-SO-NH2且可為脲、甲脲、1,1-二甲基脲、胺基甲酸苯酯、胺基甲酸乙酯或胺基甲酸丁酯。隨後移除減活化之觸媒、過量的二異氰酸酯及溶劑(假若使用)。藉由使用該減活化劑，含聚異三聚氰酸酯結構之聚異氰酸酯顯示低程度變色。JP 2-110123尚未揭示包含可進一步固化之聚異三聚氰酸酯之材料。
EP0435060揭示一種液體澆鑄組合物，其藉由使聚異氰酸酯與包含至少兩個環氧基之有機化合物以相當於異氰酸酯基相對環氧基之當量比為約1.2：1至約500：1的量及作為觸媒之第三胺反應直到藉由添加包含至少一種烷基化磺酸烷酯之穩定組分達成具有異氰酸酯基之最大65%轉化率之中間產物而製得。因為該反應不會自動終止，故須要在達成異氰酸酯基之最大65%轉化時添加穩定劑以終止該反應，這使得該製程極難提前控制。可於隨後添加選自有機膦酸烷基化或酸性酯之第三及/或第四銨鹽之熱活化觸媒且/或添加三鹵化硼與第三胺之錯合物達成進一步反應。
US2004/0176562揭示一種製造異佛爾酮二異氰酸酯(IPDI)之穩定低氣味含單體聚異三聚氰酸酯之方法。該方法涉及在四元羥烷基銨化合物的存在下進行三聚反應接著於100-160℃下進行觸媒之熱減活化。
WO 2008/068198與US 2010/0022707揭示一種使用觸媒製備寡聚聚異氰酸酯之方法，其中在已達成期望的轉化率時使用減活化劑接著移去未轉化的聚異氰酸酯。該減活化劑可尤其選自脲及含脲化合物。
EP 585835揭示一種製備含異氰尿酸酯及胺基甲酸酯基聚異氰酸酯混合物之方法，其藉由在三聚觸媒存在下部分環化二異氰酸酯，當達成期望的轉化率時使三聚觸媒減活化，隨後使所得的含異氰尿酸酯基聚異氰酸酯與羥基化合物反應然後分離除去單體二異氰酸酯而製備。
有關於利用終止三聚反應的不同方法來部分三聚化聚異氰酸酯組合物之其他揭示案為：EP 447093、US 4284730、US 4537961、US 4697014、US 4743627、US 5124370、US 5221743及US 7553963。該等揭示案中無一者揭示本發明或指向其方向。
於US 7071353中揭示異氰酸酯與羧酸之反應產物。首先形成醯胺，該醯胺接著與其他異氰酸酯基反應形成醯基脲。
已在US 6127308中揭示熱活化PIR催化。
已在US 5817732中揭示作為阻斷劑之脲及醯胺。
US 4302351揭示含異氰尿酸酯及酸式氫之阻斷劑。
根據本發明之第一態樣，揭示一種包含穩定、中間且可進一步固化之聚異三聚氰酸酯之材料。
根據本發明之該包含可進一步固化之中間聚異三聚氰酸酯之材料包含游離異氰酸酯(NCO)基，具有5-30重量%之NCO值，更佳係15-25重量%之NCO值，且其中在室溫(約20℃)及環境壓力下保存至少幾小時，更佳最短5小時，最佳24小時以上時聚異三聚氰酸酯化合物之最終濃度相對其初始值(以NCO值之變化計算得)之改變量不超過10%。
根據本發明第一態樣之包含中間且可進一步固化之聚異三聚氰酸酯之材料的優點在於可添加添加劑至包含中間聚異三聚氰酸酯之材料，諸如填充材料、纖維等。因此，該包含可進一步固化之中間聚異三聚氰酸酯之材料可進一步包含添加劑及/或黏結至以下材料，諸如木片、木屑、木薄片、木板；切碎或層狀之紙及紙板；砂、蛭石、黏土、水泥及其他矽酸鹽；磨碎膠粉、磨碎熱塑性塑料、磨碎熱固性材料；任何材料(例如紙板、鋁、木及塑料)之蜂窩構造；金屬顆粒及金屬板；顆粒狀或層狀軟木；天然纖維，例如亞麻、大麻及劍麻纖維；合成纖維，例如聚醯胺、聚烯烴、聚芳醯胺、聚酯及碳纖維；礦物纖維，例如玻璃纖維及岩棉纖維；礦物填料，例如BaSO4及CaCO3；奈米顆粒，例如黏土、無機氧化物及碳；玻璃珠、磨砂玻璃、空心玻璃珠；發泡或可發泡珠粒；未經處理或經處理之廢棄物，例如碾磨、切碎、碾碎或研磨廢棄物且特定言之飛灰；編織及非編織織物；及兩種或更多種該等材料之組合。
根據本發明之包含可進一步固化之中間聚異三聚氰酸酯之材料的其他優點在於其係一種其中可刻意終止(中斷)聚異三聚氰酸酯之形成(PIR反應)以達成聚異氰酸酯至聚異三聚氰酸酯之所期望轉化程度及因此刻意不完全固化聚異氰酸酯材料之材料。當前最先進技術之包含聚異三聚氰酸酯之材料仍包含游離NCO基，其亦可進一步固化，但只有在極高溫度的時候(通常稱為「後固化」)，於本發明範疇內，進一步固化意指在約125℃之相對低溫度下。根據本發明之進一步固化始終係在低於250℃之溫度下達成。
根據本發明之第二態樣，揭示一種製造根據本發明第一態樣之包含穩定、中間且可進一步固化之聚異三聚氰酸酯之材料之方法。
製造包含穩定中間且可進一步固化之聚異三聚氰酸酯之材料之方法至少包括以下步驟：
-提供聚異氰酸酯組合物，及接著-將含具有結構式-CO-NH2之基團之化合物與該聚異氰酸酯組合物組合及混合，及隨後或同時地，-將三聚觸媒化合物與該聚異氰酸酯組合物組合及混合，其量係使得含具有結構式-CO-NH2之基團之化合物的當量數相對三聚觸媒當量數小於4且大於0.75，較佳在介於1與3之間之範圍內，更佳在介於1.2與2之間之範圍內，最佳在介於1至1.5之間之範圍內，且接著-容許該組合物反應，及接著-視情況使該組合物冷卻降溫。
根據一實施例，容許該組合物反應之該步驟導致升溫至低於90℃之高溫而後自然冷卻降至室溫。
根據一實施例，該聚異氰酸酯組合物進一步包括較佳包含具有較佳32-6000之平均分子量及較佳1-8之平均標稱官能度之聚酯及/或聚醚多元醇的一元醇或多元醇組合物。
根據一實施例，聚異氰酸酯組合物中之該等聚異氰酸酯化合物係選自甲苯二異氰酸酯、二苯基甲烷二異氰酸酯或包含二苯基甲烷二異氰酸酯之聚異氰酸酯組合物、或該等聚異氰酸酯之混合物。
根據一實施例，該三聚觸媒化合物係選自一或多種有機鹽，較佳地，該有機鹽係選自鹼金屬、鹼土金屬及/或第四銨有機鹽，更佳係選自羧酸鹽及/或烷醇鹽，諸如乙酸鉀、己酸鉀、乙基己酸鉀、辛酸鉀、乳酸鉀、乙醇鈉、甲酸鈉、甲酸鉀、乙酸鈉、苯甲酸鉀及其混合物。
根據一實施例，該三聚觸媒化合物係選自包含LiCl及環氧樹脂之組合物，其限制條件為LiCl當量數相對環氧當量數在1：2至1：80範圍內，更佳在1：2至1：40範圍內，且又更佳在1：4至1：30範圍內。
根據一實施例，形成包含穩定、中間且可進一步固化之聚異三
聚氰酸酯之材料之方法進一步包括以下步驟：在容許包含具有含結構式-CO-NH2基團之化合物之聚異氰酸酯組合物與三聚觸媒化合物以使得聚異氰酸酯組合物中之含-CO-NH2基化合物之當量數小於或等於環氧當量數的量反應之步驟之前或之後，(另)添加環氧樹脂至聚異氰酸酯組合物。
根據本發明之第三態樣，揭示一種進一步固化包含可進一步固化之中間聚異三聚氰酸酯之材料之方法以及在進一步固化後獲得的該包含聚異三聚氰酸酯之材料。
根據本發明之進一步固化包含中間聚異三聚氰酸酯之材料或利用根據本發明第二態樣之方法獲得的包含中間聚異三聚氰酸酯之材料之方法係在環氧樹脂存在下進行。可在部分固化聚異氰酸酯組合物之製程之前或之後添加該環氧樹脂。
進一步固化包含中間聚異三聚氰酸酯之材料之方法包括在至少90℃，較佳至少100℃，更佳至少120℃，最佳等於或至少125℃之高溫下加熱包含環氧樹脂之該包含中間聚異三聚氰酸酯之材料持續至少幾分鐘及至多2小時之步驟。
根據本發明第三態樣之一實施例，進一步固化包含中間聚異三聚氰酸酯之材料之方法進一步包括在至少90℃之高溫下加熱該組合物步驟之前另添加三聚觸媒至該包含中間聚異三聚氰酸酯之材料之步驟。
根據本發明第三態樣之一實施例，進一步固化包含中間聚異三聚氰酸酯之材料之方法進一步包括在至少90℃之高溫下加熱該組合物步驟之前添加及混合添加劑及/或一或多種待黏結材料至包含中間聚異三聚氰酸酯之材料之步驟，諸如木片、木屑、木薄片、木板；切碎或層狀之紙及紙板；砂、蛭石、黏土、水泥及其他矽酸鹽；磨碎膠粉、磨碎熱塑性塑料、磨碎熱固性材料；任何材料(例如紙板、鋁、
木及塑料)之蜂窩構造；金屬顆粒及金屬板；顆粒狀或層狀軟木；天然纖維，例如亞麻、大麻及劍麻纖維；合成纖維，例如聚醯胺、聚烯烴、聚芳醯胺、聚酯及碳纖維；礦物纖維，例如玻璃纖維及岩棉纖維；礦物填料，例如BaSO4及CaCO3；奈米顆粒，例如黏土、無機氧化物及碳；玻璃珠、磨砂玻璃、空心玻璃珠；發泡或可發泡珠粒；未經處理或經處理之廢棄物，例如碾磨、切碎、碾碎或研磨之廢棄物且特定言之係飛灰；編織及非編織織物；及兩種或更多種該等材料之組合。
根據本發明第三態樣之一實施例，進一步固化包含中間聚異三聚氰酸酯之材料之方法進一步包括另一後固化步驟。
亦揭示可依上述方法獲得之包含聚異三聚氰酸酯之材料。
獨立及附屬請求項陳述本發明之特定及較佳特徵。附屬請求項之特徵可適當與獨立或其他附屬請求項之特徵組合。
自詳細說明結合考量附隨的說明本發明原理之實例當可明瞭本發明之以上及其他特性、特徵及優點。
於本發明文中，以下術語具有以下含義：
1)異氰酸酯指數或NCO指數或指數：
存在於調配物中之NCO基相對於異氰酸酯反應性氫原子之比率，表示為百分比：
換言之，NCO指數表示實際上用於調配物中之異氰酸酯相對於理論上為與用於調配物中之一定量的異氰酸酯反應性氫反應所需的異氰酸酯量之百分比。
利用基於滴定之測定法測得如實例中指明的NCO值。異氰酸酯
與過量的二-正丁基胺反應形成脲。接著以標準硝酸滴定未反應的胺至溴甲酚綠指示劑顏色改變或至電位滴定終點。NCO或NCO值百分比定義為存在於產物中之NCO基的重量百分比。
此外，應瞭解用於本文中之異氰酸酯指數自製備材料之實際聚合法視角被認為係與異氰酸酯組分及異氰酸酯反應性組分有關。在計算異氰酸酯指數中不考量在預備步驟中製得改質聚異氰酸酯(包括該等異氰酸酯衍生物，於本技藝中稱為預聚物)所消耗的任何異氰酸酯基或在預備步驟中所消耗的任何活性氫(例如，與異氰酸酯反應生成改質多元醇或聚胺)。僅考量存在於實際聚合階段之游離異氰酸酯基及游離異氰酸酯反應性氫(包括水(假若使用)之其等氫)。
2)本文中為達計算異氰酸酯指數之目的所使用的詞語「異氰酸酯反應性氫原子」係指存在於反應性組合物中的羥基及胺基中之全部活性氫原子；此意指為達計算異氰酸酯指數之目的，於實際聚合製程中，一個羥基被認為是包含一個反應性氫，一個一級胺基被認為是包含一個反應性氫及一個水分子被認為是包含兩個活性氫。
3)反應系統：組分之組合，其中聚異氰酸酯係與異氰酸酯反應性組分分開保存於一或多個容器中。
4)本文中使用術語「平均標稱羥基官能度」(或簡寫為「官能度」)指示多元醇或多元醇組合物之數目平均官能度(每分子中羥基的數目)，假設該數目平均官能度為用於其製法中之一或多種引發劑之數目平均官能度(每分子中活性氫原子的數目)，然而，其實際上通常因一些末端不飽和而稍微較小。
5)詞語「平均」係指數目平均，除非另作指明。
6)「液體」意指依ASTM D445-11a於20℃下測得其具有小於10Pa.s之黏度。
7)根據本發明之(穩定)觸媒組合物為至少包含1)根據本發明之三
聚觸媒化合物及2)根據本發明之包含具有結構式-CO-NH2之羧醯胺基之組合物。在室溫(約20℃)及環境壓力下保存至少數月時該觸媒組合物中該等個別化合物之最終濃度相對其初始濃度之改變量不超過10%。於三聚觸媒為基於LiCl之觸媒之情況中，則該LiCl總是結合環氧樹脂使用(稱為「LiCl/環氧」觸媒)使得LiCl當量數相對於環氧當量數在1：2至1：80範圍內，更佳在1：2至1：40範圍內，且又更佳在1：4至1：30範圍內。
8)根據本發明之「包含(穩定)可進一步固化之中間聚異氰酸酯之組合物」或「包含中間聚異三聚氰酸酯之材料」為包含聚異三聚氰酸酯之材料，其能夠進一步固化且藉以特定量使根據本發明之(三聚)觸媒組合物、聚異氰酸酯組合物及視需要之環氧樹脂反應持續特定時段時間藉此達到高達80℃然肯定低於90℃之溫度從而獲得包含部分固化之聚異三聚氰酸酯之材料獲得，該包含部分固化之聚異三聚氰酸酯之材料仍包含游離異氰酸酯(NCO)基，具有5-30重量%之NCO值，更佳介於15及25%之間之NCO值，且其中在室溫(約20℃)及環境壓力下保存至少幾小時至幾天且甚至長達數週，較佳1小時，更佳最短5小時，最佳24小時以上時該等聚異三聚氰酸酯化合物之最終濃度相對其初始值(以NCO值之變化計算得)之改良量不超過10%。
9)根據本發明之「包含經進一步固化之聚異三聚氰酸酯之材料」為藉由將根據本發明之包含可進一步固化之中間聚異三聚氰酸酯之材料加熱至至少90℃，較佳至少100℃，更佳至少120℃，最佳至少125℃之溫度維持至少幾分鐘使得殘餘的游離異氰酸酯基反應形成包含聚異三聚氰酸酯之化合物而獲得之包含聚異三聚氰酸酯之材料。該包含經進一步固化之聚異三聚氰酸酯之材料相較於包含中間聚異三聚氰酸酯之材料具有提高的異氰酸酯轉化率及減少的或幾乎不存在殘留游離反應性異氰酸酯基。
10)本文所用之儲藏壽命係指化合物或包含於液體中之化合物之組合物(例如，根據本發明之三聚觸媒組合物)在環境條件(室溫及環境壓力)下儲存時之穩定性，且係經計算為化合物或組合物保持低到足可用於特定處理中之黏度且仍舊適用於其所欲用途之時段。
11)本文所用之適用期係指液體反應性組合物(例如，根據本發明之可固化組合物)在環境條件(室溫及環境壓力)下儲存時之穩定性且係經計算為該反應性組合物在與反應引發劑混合、且/或經歷反應引發條件(諸如，經歷高溫)之後仍舊適用於其所欲處理之時段。
12)本文所用之三聚觸媒係指能夠催化(促進)自聚異氰酸酯形成異氰尿酸酯基之觸媒。
13)選自包含具有結構式-CO-NH2之羧醯胺基之化合物之該等化合物在本發明中亦可稱為「抑制劑」。
14)包含至少一種根據本發明之三聚觸媒化合物結合至少一種選自包含具有結構式-CO-NH2之羧醯胺基之化合物之化合物之組合物於本文中係指「三聚觸媒組合物」或「觸媒組合物」。
圖1與2顯示形成包含部分固化之聚異三聚氰酸酯之材料的溫度曲線。
圖3與4顯示新製的部分固化聚異三聚氰酸酯組合物之FTIR光譜。
根據本發明之第一態樣，揭示一種包含穩定、中間且可進一步固化之聚異三聚氰酸酯之材料。
根據本發明之包含可進一步固化之中間聚異三聚氰酸酯之材料包含游離異氰酸酯(NCO)基，具有5-30重量%之NCO值、更佳15-25重量%之NCO值，且其中在室溫(約20℃)及環境壓力下保存至少幾小
時，更佳最短5小時，最佳24小時以上時，該等聚異三聚氰酸酯化合物之最終濃度相對其初始值之改變量不超過10%。包含可進一步固化之中間聚異三聚氰酸酯之材料較佳包括含具有結構式-CO-NH2之基團之化合物及三聚觸媒化合物。
根據本發明之第二態樣，揭示一種藉由使用三聚觸媒組合物製備根據本發明第一態樣之包含穩定、中間且可進一步固化之聚異三聚氰酸酯之材料的方法。
該三聚觸媒組合物為包含三聚觸媒結合包含具有結構式-CO-NH2之羧醯胺基之化合物之穩定組合物。該穩定三聚觸媒組合物在20℃及環境壓力下具有至少數月及更長之長儲藏壽命。
吾人已驚人地發現可以中斷(終止)聚異氰酸酯組合物中之聚異氰酸酯三聚觸媒的催化活性。為了達成該中斷，可使用適於由聚異氰酸酯結合當前最先進技術中可採行之包含具有結構式-CO-NH2之羧醯胺基之化合物開始形成包含聚異三聚氰酸酯之材料之任何三聚觸媒。該等觸媒之實例為金屬或第四銨羧酸鹽及烷醇鹽、第三胺衍生物、LiCl結合環氧(LiCl/環氧觸媒)等。
吾人已驚人地發現可以中斷及再活化聚異氰酸酯組合物中之聚異氰酸酯三聚觸媒之催化活性。該三聚觸媒較佳係選自有機鹽，較佳地，選自鹼金屬、鹼土金屬及/或第四銨有機鹽。更佳地，該有機鹽係選自羧酸鹽或烷醇鹽及其混合物，該羧酸根/烷醇根基團較佳具有1-12個碳原子、及其混合物。較佳之實例為羧酸鈉、羧酸鉀、烷醇鈉及烷醇鉀。或者，可藉由使用LiCl當量數相對於環氧當量數在1：2至1：80範圍內，更佳在1：2至1：40範圍內，且又更佳在1：4至1：30範圍內之LiCl/環氧觸媒中斷及再活化聚異氰酸酯組合物中之聚異氰酸酯三聚觸媒的催化活性。
聚異氰酸酯三聚觸媒催化活性之中斷及/或再活化係藉由添加三
聚觸媒結合選自包含具有結構式-CO-NH2之羧醯胺基之化合物之化合物至聚異氰酸酯組合物以致包含羧醯胺基之化合物相對於觸媒之比率對應於預定比率隨後使該聚異氰酸酯組合物經歷預定加熱步驟而實現。
添加根據本發明之觸媒組合物至聚異氰酸酯(組合物)且隨後容許該組合物視情況與至少一種環氧樹脂化合物反應而升溫至高溫(低於90℃)。取決於該組合物中不同組分間之比率及處理條件，將會達成大於或小於高溫(低於90℃)。該反應將會在特定點終止並冷卻降至室溫(自身自然地)以致獲得包含穩定部分固化之聚異氰酸酯之組合物或包含中間聚異三聚氰酸酯之材料。由於形成包含聚異三聚氰酸酯之材料係放熱故無需額外加熱即可達到約80℃之高溫。
三聚反應之此中斷形成部分固化之聚異氰酸酯材料或(換言之)包含中間聚異三聚氰酸酯之材料，當意欲在製造最終固化產品之前根據要求特定黏度之方法製造產品時，該等材料可能係特別理想。於所有該等方法中，期望單組分組合物作為起始物質，其具有特定黏度程度，且於環境條件下在給定時段內顯示未反應或小程度反應，以容許該等組合物以該等方法進行處理。
吾人已驚人地發現，藉由使用具有三聚觸媒相對於包含具有結構式-CO-NH2之羧醯胺基之化合物之特定比之三聚觸媒組合物，包含中間(部分固化)聚異三聚氰酸酯之材料之適用期可長達數日及更長，而不會不利地影響後來的部分固化之聚異氰酸酯組合物或中間聚異三聚氰酸酯材料之最終固化。
該觸媒組合物包含選自包含具有結構式-CO-NH2之羧醯胺基之化合物之化合物，此意指形成包含-CO-NH-CO-基之化合物及更特定言之包含具有結構式-CO-NH-CO-NH-之醯脲基之化合物，其為聚異氰酸酯化合物與包含具有結構式-CO-NH2之羧醯胺基之化合物於添加至
聚異氰酸酯組合物之後之反應產物。
為了容許中斷三聚反應，添加至聚異氰酸酯組合物之選自包含具有結構式-CO-NH2之化合物之化合物的當量數比添加至聚異氰酸酯組合物之三聚觸媒的當量數小四倍及比該三聚觸媒當量數高0.75倍。較佳地，選自包含具有結構式-CO-NH2之羧醯胺基之化合物之化合物的當量數相對於三聚觸媒當量數在介於1至3之間之範圍內，更佳在介於1.2及2之間之範圍內，以形成根據本發明之包含「穩定」中間聚異三聚氰酸酯之材料。最佳地，包含具有結構式-CO-NH2之羧醯胺基之化合物的當量數相對於三聚觸媒當量數在介於1與1.5之間之範圍內。包含具有結構式-CO-NH2之羧醯胺基之化合物的當量數相對於三聚觸媒當量數之比率可為1或接近1。
於所有情況中，該聚異氰酸酯組合物中之含-CO-NH-CO-基之化合物之最終濃度為致使-CO-NH-CO-基相對於異氰酸酯基數目之比率為至多1，較佳至多0.01，更佳至多0.0015之濃度。
根據本發明第一態樣之一較佳實施例，該三聚觸媒係選自有機鹽，較佳地，選自鹼金屬、鹼土金屬及/或第四銨有機鹽。更佳地，該有機鹽係選自羧酸鹽或烷醇鹽及其混合物，該羧酸根/烷醇根基團較佳具有1-12個碳原子、及其混合物。較佳之實例為羧酸鉀、羧酸鈉、烷醇鈉及烷醇鉀。具有環結構之羧酸鹽/烷醇鹽(諸如苯甲酸鈉及苯甲酸鉀)亦為適宜之三聚觸媒。最佳之實例為乙酸鉀、己酸鉀、乙基己酸鉀、辛酸鉀、乳酸鉀、N-羥丙基三甲基辛酸銨、N-羥丙基三甲基甲酸銨及其混合物。適宜之觸媒可商業購得；實例為購自Huntsman之觸媒LB或購自Air Products之Dabco K2097(包含乙酸鉀)、及Dabco K15(包含辛酸鉀)。或者，該三聚觸媒係選自LiCl/環氧觸媒，其限制條件為LiCl當量數相對環氧當量數在1：2至1：80範圍內，更佳在1：2至1：40範圍容，且又更佳在1：4至1：30範圍內。
包含羧醯胺之化合物較佳係選自如式NH2-CO-R6之化合物，其中R6為1)氫(-H)、2)-NR8R9、3)具有1-20個碳原子且視情況包含羥基、醚、鹵素及/或胺基之烴基、或4)-R10-CO-NH2，其中R8與R9彼此獨立地選自氫、羥基、鹵素及烴基，該等烴基具有1-10個碳原子且視情況包含羥基、醚、鹵素及/或胺基且其中R10為具有至多8個碳原子之二價烴基。亦可使用該等羧醯胺之混合物。較佳地，該等羧醯胺具有至多499之分子量。
該等羧醯胺中之烴基可為直鏈或分支鏈、飽和或不飽和及環狀或非環狀；其等可為脂族、芳族或芳脂族。
更佳之羧醯胺為其中R6為1)-NR8R9、2)具有1-10個碳原子且視情況包含1-3個羥基及/或醚基之烷基、3)苯基或4)甲苯基之彼等，其中R8與R9彼此獨立地選自氫、羥基、苯基、甲苯基及具有1-6個碳原子且視情況包含羥基及/或醚基之烷基。亦更佳為該等更佳化合物之混合物。
極適用的羧醯胺(NH2-CO-R6)之實例為以下者：
最佳使用碳醯二胺(脲)。應注意於計算羧醯胺當量數中，碳醯二胺(脲)被認為係含有2個羧醯胺基。
根據一實施例，添加及混合該三聚觸媒至選自包含具有結構式-CO-NH2之羧醯胺基之化合物之抑制劑化合物，以形成穩定三聚觸媒組合物。在進行三聚觸媒之混合之前，宜可先將三聚觸媒及/或包含羧醯胺基之化合物溶解於例如有機溶劑之溶劑中，例如醇，例如甲醇或乙醇。隨後，必要時可汽提移除溶劑。於環境條件或高溫(例如40-70℃)下進行預混合及混合且藉由一般攪拌完成。
一般而言，根據本發明之一或多種聚異氰酸酯化合物可選自脂族聚異氰酸酯且較佳選自芳族聚異氰酸酯。較佳之脂族聚異氰酸酯為六亞甲基二異氰酸酯、異佛爾酮二異氰酸酯、二環己基甲烷二異氰酸酯及環己烷二異氰酸酯而較佳之芳族聚異氰酸酯為甲苯二異氰酸酯、萘二異氰酸酯、四亞甲基二異氰酸酯、伸苯二異氰酸酯、聯甲苯胺二異氰酸酯，且特別係二苯基甲烷二異氰酸酯(MDI)及包含二苯基甲烷二異氰酸酯之聚異氰酸酯組合物(例如，所謂的聚合MDI、粗製
MDI、經脲酮亞胺改質的MDI及具有由MDI及包含MDI之聚異氰酸酯產生之游離異氰酸酯基之預聚物)及該等聚異氰酸酯之混合物。MDI及包含MDI之聚異氰酸酯組合物為最佳且尤其係選自以下之其等：1)包含至少35重量%，較佳至少60重量% 4,4'-二苯基甲烷二異氰酸酯(4,4'-MDI)之二苯基甲烷二異氰酸酯；2)聚異氰酸酯1)之經碳二亞胺及/或脲酮亞胺改質之變型，該變型具有20重量%或更大之NCO值；3)聚異氰酸酯1)及/或2)之經胺基甲酸酯改質之變型，該變型具有20重量%或更大之NCO值且為過量的聚異氰酸酯1)及/或2)及具有2-4之平均標稱羥基官能度及至多1000之平均分子量之多元醇之反應產物；4)包含含3個或更多個異氰酸酯基之同系物之二苯基甲烷二異氰酸酯；5)預聚物，其具有5-30重量%之NCO值且為聚異氰酸酯1)-4)中任何一或多者及具有2-4之平均標稱羥基官能度及大於1000至8000之平均分子量之多元醇之反應產物；及6)任何前述聚異氰酸酯之混合物。
聚異氰酸酯1)包含至少35重量%之4,4'-MDI。該等聚異氰酸酯為相關技藝熟知且包括純4,4'-MDI及4,4'-MDI、2,4'-MDI及2,2'-MDI之異構體混合物。應注意該異構體混合物中之2,2'-MDI的量係處於雜質水準且一般將不超過2重量%，其餘為4,4'-MDI及2,4'-MDI。諸如其等之聚異氰酸酯為相關技藝熟知且可商業購得；例如，SuprasecR MPR及1306來自Huntsman(Suprasec為Huntsman公司或其分公司已在一或多個(但非全部)國家註冊之商標)。
上述聚異氰酸酯1)之經碳二亞胺及/或脲酮亞胺改質之變型亦為相關技藝熟知且可商業購得；例如，SuprasecR 2020來自Huntsman。上述聚異氰酸酯1)之經胺基甲酸酯改質之變型亦為相關技藝熟知，參見：例如，G.Woods之The ICI Polyurethanes Book(1990年，第2版)之第32-35頁。
聚異氰酸酯4)亦廣為吾人所知且可商業購得。該等聚異氰酸酯通
常稱為粗製MDI或聚合MDI。實例為來自Huntsman之SuprasecR 2185、SuprasecR 5025及SuprasecR DNR。
預聚物(聚異氰酸酯5))亦廣為吾人所知且可商業購得。實例為SuprasecR 2054及SuprasecR 2061，其等均來自Huntsman。
亦可使用前述聚異氰酸酯之混合物，參見：例如，G.Woods之The ICI Polyurethanes Book(1990年，第2版)之第32-35頁。此種可商業購得的聚異氰酸酯之一實例為來自Huntsman之SuprasecR 2021。
添加根據本發明之具有-CO-NH2基之化合物後之聚異氰酸酯組合物之NCO值之範圍可為10至48重量%且較佳係20至33重量%。
根據一實施例，為了形成本發明之包含穩定中間聚異三聚氰酸酯之組合物，藉由添加選自包含具有結構式-CO-NH2之羧醯胺基之化合物之化合物至聚異氰酸酯組合物而在該聚異氰酸酯組合物之原位形成具有-CO-NH-CO-基之化合物。可在添加包含羧醯胺基之化合物同時或剛好在聚異氰酸酯組合物中添加包含羧醯胺基之化合物之後添加三聚觸媒。假若在添加包含羧醯胺基之化合物同時添加三聚觸媒，則包含具有結構式-CO-NH2之羧醯胺基之化合物的當量數相對於觸媒化合物當量數應小於4且大於0.75。較佳地，包含具有結構式-CO-NH2之羧醯胺基之化合物的當量數相對於觸媒化合物當量數在介於1及3之間之範圍內，更佳在介於1.2及2之間之範圍內。最佳地，包含具有結構式-CO-NH2之羧醯胺基之化合物的當量數相對觸媒化合物當量數在介於1至1.5之間之範圍內。包含具有結構式-CO-NH2之羧醯胺基之化合物的當量數相對於三聚觸媒當量數之比率可為1或接近1。
根據另一實施例，可先添加根據本發明之三聚觸媒組合物至一元醇/多元醇組合物。不論是觸媒化合物或選自包含具有結構式-CO-NH2之羧醯胺基之化合物之抑制劑化合物均可單獨或以組合方式添加至多元醇組合物。較佳地，該多元醇組合物包含具有32-6000之平均
分子量及1-8之平均標稱官能度之聚酯及/或聚醚多元醇。可接著將該多元醇組合物添加至聚異氰酸酯組合物且可導致形成根據本發明之包含穩定中間聚異三聚氰酸酯之組合物，其進一步包含聚異氰酸酯預聚物。於包含穩定中間聚異三聚氰酸酯之組合物中之該等預聚物具有殘留的游離NCO基且具有5-30重量%之NCO值，更佳介於15及25%之間之NCO值，且為一或多種聚異氰酸酯化合物與一或多種多元醇化合物之反應產物。
可在包括添加及混合上述穩定三聚觸媒組合物至聚異氰酸酯組合物且容許該組合物視情況與至少一種環氧樹脂化合物反應之製程之後獲得包含穩定中間聚異三聚氰酸酯之材料。該反應混合物將開始反應，隨後達到高溫(低於90℃)而後自然終止(冷卻降至室溫)。換言之，該反應混合物將達到高溫(低於90℃)但隨後因組合物中存在一定程度的抑制劑分子而終止進一步之反應(固化)。
根據本發明之包含穩定中間聚異三聚氰酸酯之材料可用於多種應用中。舉例而言，其特別適於製造用以製造具有高Tg之印刷電路板的半固化片，適於作為機罩下方之零件用於汽車應用。其亦可用於製造作為反應性中間物用以製造大型及輕重量複合零件之片狀成型複合材料(SMC)或塊狀成型複合材料(BMC)。可在特定及可控條件(諸如真空、氮氣或低溫(於冷凍機中))下儲存預先反應的聚異三聚氰酸酯組合物(根據本發明之包含中間且經進一步固化之聚異三聚氰酸酯之材料)、或由其製成之市售產品(諸如預浸材)，以延長其適用期。
視情況，可進一步添加選自一元醇及/或多元醇，較佳選自聚酯及/或聚醚多元醇之醇至包含穩定中間聚異三聚氰酸酯之材料。
根據本發明之第三態樣，揭示一種進一步固化包含中間聚異三聚氰酸酯之材料的方法。
根據本發明第一態樣之包含中間聚異三聚氰酸酯之材料係穩定
且可用於進一步固化。此種包含經進一步固化之聚異三聚氰酸酯之組合物係藉由至少添加環氧樹脂至包含中間聚異三聚氰酸酯之組合物(假若尚不存在)且加熱至高於90℃，較佳高於100℃，更佳高於120℃，最佳等於或高於125℃之高溫而獲得。包含中間聚異三聚氰酸酯之材料可呈液體、糊劑、或甚至固體形式等，其取決於容許包含中間聚異三聚氰酸酯之材料反應到何種程度(根據第一態樣)。
根據本發明之包含中間聚異三聚氰酸酯之材料應包含至少一種環氧樹脂以容許進一步固化及/或獲得完全固化之聚異三聚氰酸酯材料。較佳地，包含中間聚異三聚氰酸酯之材料中之具有-CO-NH-CO-基之化合物當量數係小於或等於存於及/或添加至該包含中間聚異三聚氰酸酯之組合物之環氧當量數。
根據一實施例，用於製造包含中間聚異三聚氰酸酯之材料之三聚觸媒可選自如本發明第一態樣之實施例中所述之任何當前最先進技術三聚觸媒。於在部分固化之聚異氰酸酯組合物或中間聚異三聚氰酸酯材料中中斷三聚反應之後，可在視情況進一步添加如本發明第一態樣之實施例中所述之選自鹼金屬、鹼土金屬、第四銨有機鹽觸媒及/或LiCl/環氧觸媒之三聚觸媒材料且隨後加熱該中間聚異三聚氰酸酯材料至高於90℃，較佳高於100℃，更佳高於120℃，最佳等於或高於125℃之溫度之後進一步固化該部分固化之聚異氰酸酯組合物。更佳地，該三聚觸媒係選自羧酸鹽或烷醇鹽及其混合物，該羧酸根/烷醇根基團較佳具有1-12個碳原子、及其混合物。
根據一實施例，用於製造包含中間聚異三聚氰酸酯之材料之三聚觸媒係選自有機鹽，較佳地，選自鹼金屬、鹼土金屬、第四銨有機鹽及/或LiCl/環氧觸媒。更佳地，如本發明第一態樣之實施例中所述，該有機鹽三聚觸媒係選自羧酸鹽或烷醇鹽及其混合物，該羧酸根/烷醇根基團較佳具有1-12個碳原子、及其混合物。較佳之實例為羧
酸鉀、羧酸鈉、烷醇鈉及烷醇鉀。於在部分固化之聚異氰酸酯組合物或中間聚異三聚氰酸酯材料中中斷三聚反應之後，可藉由加熱該中間聚異三聚氰酸酯材料至高於90℃，較佳高於100℃，更佳120℃，最佳等於或高於125℃之溫度再活化三聚觸媒之催化活性。包含中間聚異三聚氰酸酯之材料應包含至少一種環氧樹脂以容許進一步固化及/或獲得完全固化之聚異三聚氰酸酯材料。假若環氧樹脂已作為LiCl/環氧三聚觸媒之一部分存在，則存在於LiCl/環氧三聚觸媒中之環氧樹脂的量可能不足以進一步固化，於此情況中，必須另外添加環氧樹脂用於進一步固化。
在最終固化包含穩定中間聚異三聚氰酸酯之組合物之前，可將該包含穩定中間聚異三聚氰酸酯之組合物饋入模具中以賦予其特定形狀或饋入物件腔內以使該物件具有聚異三聚氰酸酯內部或饋至其表面上以使此表面具有聚異三聚氰酸酯覆蓋層，或可將其用於修補物件且特別係藉由施用其至此物件之內部及/或外部表面來修補管。
使用的環氧樹脂較佳係選自20℃時為液體之任何環氧樹脂。
環氧樹脂之實例為：
I)聚縮水甘油基及聚(β-甲基縮水甘油基)酯，其可藉由使分子中具有至少兩個羧基之化合物分別與表氯醇及β-甲基表氯醇反應獲得。在鹼存在下可方便地實現該反應。
脂族聚羧酸可用為分子中具有至少兩個羧基之化合物。該等聚羧酸之實例為草酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸及二聚或三聚亞麻油酸。
然而，亦可使用環脂族聚羧酸，諸如(例如)四氫鄰苯二甲酸、4-甲基四氫鄰苯二甲酸、六氫鄰苯二甲酸或4-甲基六氫鄰苯二甲酸。
此外，可使用芳族聚羧酸，諸如(例如)鄰苯二甲酸、間苯二甲酸或對苯二甲酸。
II)聚縮水甘油基或聚(β-甲基縮水甘油基)醚，其可藉由在鹼性條件或酸性觸媒的存在下隨後以鹼處理使具有至少兩個游離醇式羥基及/或酚系羥基之化合物與表氯醇或β-甲基表氯醇反應而獲得。
此類型縮水甘油醚係衍生自(例如)非環狀醇，例如乙二醇、二乙二醇或高碳數聚(氧伸乙基)二醇、丙烷-1,2-二醇或聚(氧伸丙基)二醇、丙烷-1,3-二醇、丁烷-1,4-二醇、聚(氧伸丁基)二醇、戊烷-1,5-二醇、己烷-1,6-二醇、己烷-2,4,6-三醇、甘油、1,1,1-三羥甲基丙烷、異戊四醇或山梨糖醇、及聚表氯醇。此類型之其他縮水甘油醚係衍生自環脂族醇，諸如1,4-環己烷二甲醇、雙(4-羥基環己基)甲烷或2,2-雙(4-羥基環己基)丙烷、或衍生自包含芳族基及/或其他官能基之醇(諸如N,N-雙(2-羥乙基)苯胺或p,p'-雙(2-羥乙基胺基)-二苯基甲烷)。
該等縮水甘油醚亦可基於單核苯酚，諸如(例如)對第三丁基苯酚、間苯二酚或氫醌，或基於多核苯酚，諸如(例如)雙(4-羥苯基)甲烷、4,4'-二羥基聯苯、雙(4-羥苯基)碸、1,1,2,2-肆(4-羥苯基)乙烷、2,2-雙(4-羥苯基)丙烷或2,2-雙(3,5-二溴-4-羥基苯基)丙烷。
適於製備縮水甘油醚之其他羥基化合物為酚醛樹脂，其可藉由醛(諸如甲醛、乙醛、氯醛或呋喃甲醛)與未經取代或經氯原子或C1-C9-烷基取代之苯酚或雙酚(諸如(例如)苯酚、4-氯苯酚、2-甲基苯酚或4-第三丁基苯酚)之縮合獲得。
III)聚(N-縮水甘油基)化合物，其可藉由表氯醇與含有至少兩個胺氫原子之胺之反應產物脫去氯化氫獲得。該等胺為(例如)苯胺、正丁胺、雙(4-胺基苯基)甲烷、間亞二甲苯基二胺或雙(4-甲基胺基苯基)甲烷。
該等聚(N-縮水甘油基)化合物亦包括異氰尿酸三縮水甘油酯、環伸烷基脲(諸如伸乙基脲或1,3-伸丙基脲)之N,N'-二縮水甘油衍生物、及乙內醯脲(諸如5,5-二甲基乙內醯脲)之二縮水甘油衍生物。
IV)聚(S-縮水甘油基)化合物，例如二-S-縮水甘油衍生物，其係衍生自二硫醇，諸如(例如)乙烷-1,2-二硫醇或雙(4-巰基甲基苯基)醚。
V)環脂族環氧樹脂，諸如(例如)雙(2,3-環氧環戊基)醚、2,3-環氧環戊基縮水甘油醚、1,2-雙(2,3-環氧環戊基氧基)乙烷或3,4-環氧環己基甲基-3',4'-環氧環己烷羧酸酯。
亦可使用其中1,2-環氧基鍵結不同雜原子或官能基之環氧樹脂；該等化合物包括(例如)4-胺基苯酚之N,N,O-三縮水甘油衍生物、水楊酸之縮水甘油醚-縮水甘油酯、N-縮水甘油基-N'-(2-縮水甘油氧基丙基)-5,5-二甲基乙內醯脲或2-縮水甘油氧基-1,3-雙(5,5-二甲基-1-縮水甘油基乙內醯脲-3-基)丙烷。
尤佳為彼等於I與II中提及者且最佳為彼等於II中提及者。
假若使用含有羥基或其他異氰酸酯反應性氫之環氧樹脂，則在計算指數或羥基當量數中不考量該等羥基及氫。
在形成包含穩定中間聚異三聚氰酸酯之材料之前或之後，可添加添加劑至該材料或其成分以致可藉由利用常用的製造方法製得(例如)複合材料。添加劑之實例為填料、纖維等。該等添加劑(當前最先進技術中亦稱為「欲黏結材料」)較佳於室溫下為固體材料。可使用材料之實例為：木片、木屑、木薄片、木板；切碎或層狀之紙及紙板；砂、蛭石、黏土、水泥及其他矽酸鹽；磨碎膠粉、磨碎熱塑性塑料、磨碎熱固性材料；任何材料(例如紙板、鋁、木及塑料)之蜂窩構造；金屬顆粒及金屬板；顆粒狀或層狀軟木；天然纖維，例如亞麻、大麻及劍麻纖維；合成纖維，例如聚醯胺、聚烯烴、聚芳醯胺、聚酯及碳纖維；礦物纖維，例如玻璃纖維及岩棉纖維；礦物填料，例如BaSO4及CaCO3；奈米顆粒，例如黏土、無機氧化物及碳；玻璃珠、磨砂玻璃、空心玻璃珠；發泡或可發泡珠粒；未經處理或經處理之廢
棄物，例如碾磨、切碎、碾碎或研磨廢棄物且特定言之係飛灰；編織及非編織織物；及兩種或更多種該等材料之組合。
其他添加劑實例為其他非異氰酸酯反應性溶劑、多元醇及一元醇、其他觸媒、發泡劑、表面活性劑、水淨化劑(例如原甲酸烷酯及特定言之係原甲酸三異丙酯)、抗微生物劑、阻燃劑、防煙劑、UV-穩定劑、著色劑、塑化劑、模具內部釋離劑、流變改質劑、潤濕劑、分散劑及填料。
視情況用於本發明中之一元醇及/或多元醇較佳具有1-8之平均標稱羥基官能度及32-8000之平均分子量。亦可使用一元醇及/或多元醇之混合物。
該等一元醇之實例為甲醇、乙醇、丙醇、丁醇、苯酚、環己醇及具有32-6000之平均分子量之一元烴醇，例如，脂族及聚醚一元醇。多元醇之實例為乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、三丙二醇、三羥甲丙烷、山梨糖醇、蔗糖、甘油、乙二醇、丙二醇、丁二醇、戊二醇、己二醇、相比該等化合物具有更多碳原子且具有至多8000之分子量之芳族及/或脂族多元醇、具有200-8000之平均分子量之聚酯多元醇、具有200-8000之平均分子量之聚醚聚酯多元醇及具有200-8000之平均分子量之聚醚多元醇。該等一元醇及多元醇可商業購得。適用的實例為Daltocel F555及Daltocel F442(其等均為購自Huntsman之聚醚三醇)、Voranol P400及Alcupol R1610(其等分別為購自DOW及Repsol之聚醚多元醇)、及Priplast 1838及3196(其等為購自Croda之高分子量聚酯多元醇)、及Capa 2043多元醇(其為購自Perstorp之平均MW為約400之直鏈聚酯二醇)、及K-flex polyols 188及A308(其等為購自King Industries之分別具有約500及430之MW之聚酯多元醇)、及芳族聚酯多元醇，例如，分別具有約2000及600之平均分子量之Stepanpol PH56及BC180、及Neodol 23E(其為購自Shell之脂族一元
醇)。
最佳為具有200-6000之平均分子量及1-8之平均標稱官能度之聚酯及聚醚多元醇。
可視需要使用之不含異氰酸酯反應性基團之溶劑較佳為20℃時為液體之有機溶劑。依ASTM D445-11a測得於20℃時具有3000 mPa.s或更小之黏度之溶劑視為液體溶劑。最佳為20℃時每升溶劑能夠溶解大於1 mg之含-CO-NH-CO-基之特定化合物之有機液體溶劑。
當然基於上述原則，熟習本技藝者可輕易判定有機液體是否適於作為本發明中的溶劑使用。適宜溶劑之實例為酯(諸如乙酸乙酯、乙酸丙酯、碳酸丙烯酯、酞酸酯)、酮(諸如丙酮、甲基乙基酮、甲基異丁基酮、環己酮)、脂族烴(諸如環己烷、庚烷)、氯代烴(諸如氯仿、二氯甲烷)、芳族溶劑(諸如苯、甲苯)、醚(諸如二甲醚、二乙醚、二噁烷、四氫呋喃)及其混合物。最佳選擇在環境壓力或真空下具有低沸點之溶劑(接著，其等可輕易地自可固化組合物汽提除去)。較佳地，其等溶劑應能夠溶解至少10 g羧醯胺/kg溶劑。溶劑的量可在寬範圍之間改變。藉由包含羧醯胺之化合物的期望類型及量及其於所選擇溶劑中之溶解度確定下限。藉由考慮方便性及成本來確定上限：越少越好。
以以下實例說明本發明。
使用的化學品：
Suprasec 2020聚異氰酸酯(來自Huntsman)：為經脲酮亞胺改質之聚異氰酸酯，在該等實例中表示為S2020
碳醯二胺(脲)99%+有機物(來自Acros)
Araldite DY-T(來自Huntsman)，為三羥甲丙烷之三縮水甘油醚，本文中表示為DY-T。
Alcupol R1610(來自Repsol)，為具有160 mg KOH/g之OH值之甘油聚氧伸丙基多元醇
Dabco K2097(來自Air Products)，為50重量%含於二乙二醇中之乙酸鉀溶液
Jeffcat TR-90(來自Huntsman)，為1,3,5-叁(3-(二甲胺基)丙基)-六氫-s-肼觸媒
Daltocel F526為聚乙烯三醇(來自Huntsman)，本文中稱為F526，其具有127 mg KOH/g之OH值
以30重量%含於水中之四甲基甲酸銨溶液(純度>99.99%)(來自Sigma Aldrich)，本專利中稱為TMA甲酸鹽
Araldite、Suprasec、Jeffamine、Jeffcat及Daltocel為Huntsman公司或其分公司之商標且已在一或多個(但非全部)國家註冊。
在以下實例中均未觀察到雙縮脲形成。
實例1至9闡述根據本發明之穩定三聚觸媒組合物之製法，其包含具有結構式-CONH2之羧醯胺基團及三聚觸媒。實例10至18闡述根據本發明之包含穩定部分固化之聚異氰酸酯之組合物之製法。實例19至27闡述根據本發明之包含最終固化之聚異三聚氰酸酯之組合物之製法。
首先將製備實例1至5之觸媒組合物時所需的必需量的脲碳醯二胺添加至必需量的Daltocel F526，且讓其溶解於預先加熱至100℃之該多元醇中，同時攪拌。反應進行約一小時之後，獲得含脲碳醯二胺之Daltocel F526透明流動及均勻溶液。
接著，於室溫下將必需量的前面所製得溶液與必需量的Alcupol R1610及Dabco K2097觸媒混合約15分鐘，以製備述於表1中之穩定三聚觸媒組合物。
依照與實例1至5相同的程序，但改用30重量%含於水中之四甲基甲酸銨溶液作為三聚觸媒替代Dabco K2097，製備穩定三聚觸媒組合物6與7。
Daltocel F526、脲碳醯二胺、Alcupol R1610及四甲基甲酸銨之反應量概述於表1中。
依照與實例1至5相同之程序，但改用Jeffcat TR-90作為三聚觸媒替代Dabco K2097，製備穩定三聚觸媒組合物8與9。
Daltocel F526、脲碳醯二胺、Alcupol R1610及Jeffcat TR-90之反應量概述於表1中。
以漸增方式(每分鐘約1 g)將14 pbw之表1穩定三聚觸媒組合物添加至含於適宜體積之容器中於室溫下維持攪拌之85 pbw Suprasec 2020，以形成根據本發明之包含部分固化之聚異三聚氰酸酯之組合物。
隨著反應的進行，反應混合物之溫度漸增至摻合物溫度，無需任何額外的外部熱源，然後一旦預反應步驟完成本身再次降溫。使所得的部分固化之聚異三聚氰酸酯組合物冷卻降至室溫，且於使用之前，於氮氣氛圍下儲存於封閉容器中。
製備包含部分固化之聚異三聚氰酸酯之材料之一些實例之溫度曲線提供於圖1與2中。
於所有該等實例中，藉由利用ATR裝置之紅外光譜法(FTIR)證實聚異三聚氰酸酯基之存在給予約1410 cm-1及1705 cm-1之特徵吸光度。該FTIR光譜之少數實例提供於圖3與4中。
最後，一旦冷卻降至室溫(於製得後約1小時30分鐘時)，即刻依照針對於NCO滴定之Huntsman內部程序PU/IV-1，包括使異氰酸酯與過量的正二丁胺反應形成脲，來滴定上述部分固化之聚異三聚氰酸酯組合物之NCO值。接著利用標準硝酸滴定未反應的胺至溴甲酚綠指示劑顏色改變或電位滴定終點。NCO或NCO值之百分比定義為存在於產物中的NCO基之重量百分比。
於24小時後依照相同程序再檢驗NCO值，以評估該等摻合物之穩定性：於室溫下24小時後改變小於10%。
使用的成分(其含量單位為重量份)、新製及製得一天後的組合物之-NCO值、及每分子觸媒中具有-CONH2之羧醯胺分子之當量比提供於表2中。
將給定量的Araldite DY-T環氧樹脂添加至前面所製得的維持於室溫或再次短時間加熱至40至50℃以使其更具流動性之包含聚異三聚氰酸酯之材料，然後混合幾分鐘，以獲得可進一步固化之聚異三聚氰酸酯組合物。
於實例28中，再次製得與實例18相同的包含部分固化之聚異三聚氰酸酯之材料。於冷卻降至室溫之後，添加5 pbw之以6重量% Dabco K2097之Alcupol R1610、及10 pbw之Araldite DY-T，及混合幾分鐘。
容許30 g實例19至28之如此獲得的樹脂組合物於150℃下在4 mm深敞開模具中固化2小時，以製得本發明之包含完全固化之聚異三聚氰酸酯之材料。
藉由於TA Q800設備上之示差機械熱分析(DMTA)以3℃/min之加熱速率及1 Hz之頻率(依照ASTM 4065測得)測定所得材料之玻璃化轉
變溫度(Tg)。Tg定義為利用TA通用分析軟體獲得的儲存模數(E')曲線之第一拐點。
使用的成分、包含經固化之聚異三聚氰酸酯之材料之Tg、及每具有-CONH2基之分子中環氧基之當量比提供於表3中。
Claims (14)
- 一種製造包含穩定、中間且可進一步固化之聚異三聚氰酸酯之材料的方法，該材料含有游離異氰酸酯(NCO)基，具有5-30重量%之NCO值，更佳係15-25重量%之NCO值，及其中當在室溫(約20℃)及環境壓力下保存至少數小時，更佳最短5小時，最佳24小時以上時，聚異三聚氰酸酯化合物之最終濃度相對其初始值之改變量不超過10%(以NCO值之變化計算)，該方法至少包括以下步驟：提供聚異氰酸酯組合物，及接著將包含具有結構式-CO-NH2之基團之化合物與該聚異氰酸酯組合物組合及混合，及隨後或同時地，將三聚觸媒化合物與該聚異氰酸酯組合物組合及混合，其組合量係使得包含具有結構式-CO-NH2之基團之化合物之當量數相對於三聚觸媒當量數小於4且大於0.75，較佳在介於1與3之間之範圍內，更佳在介於1與2之間之範圍內，最佳在介於1至1.5之間之範圍內，及接著容許該組合物反應，及接著視情況使該組合物冷卻降溫。
- 如請求項1之方法，其中容許該組合物反應之該步驟導致升溫至低於90℃之高溫而後自然冷卻降至室溫。
- 如請求項1至2中任一項之方法，其中該聚異氰酸酯組合物進一步包括較佳包含具有較佳32-6000之平均分子量及較佳1-8之平均標稱官能度之聚酯及/或聚醚多元醇的一元醇或多元醇組合物。
- 如請求項1至2中任一項之方法，其中該聚異氰酸酯組合物中之該等聚異氰酸酯化合物係選自甲苯二異氰酸酯、二苯基甲烷二 異氰酸酯或包含二苯基甲烷二異氰酸酯之聚異氰酸酯組合物、或該等聚異氰酸酯之混合物。
- 如請求項1至2中任一項之方法，其中該三聚觸媒化合物係選自一或多種有機鹽，該有機鹽較佳選自鹼金屬、鹼土金屬及/或四級銨有機鹽，更佳選自羧酸鹽及/或烷醇鹽，諸如乙酸鉀、己酸鉀、乙基己酸鉀、辛酸鉀、乳酸鉀、乙醇鈉、甲酸鈉、甲酸鉀、乙酸鈉、苯甲酸鉀及其混合物。
- 如請求項1至2中任一項之方法，其中該三聚觸媒化合物係選自包含LiCl及環氧樹脂之組合物，其限制條件為LiCl當量數相對於環氧當量數係在範圍1：2至1：80內，更佳在範圍1：2至1：40內，及最佳在1：4至1：30內。
- 如請求項1至2中任一項之方法，其進一步包括以下步驟：在容許包含具有含結構式-CO-NH2基團之化合物之聚異氰酸酯組合物與三聚觸媒化合物以使得聚異氰酸酯組合物中之含-CO-NH2基之化合物之當量數小於或等於環氧當量數的量反應之步驟之前或之後，(另)添加環氧樹脂至該聚異氰酸酯組合物。
- 一種依照如請求項1至7中任一項之方法獲得之包含穩定、中間且可進一步固化之聚異三聚氰酸酯之材料。
- 如請求項8之包含可進一步固化之中間聚異三聚氰酸酯之材料，其進一步包含添加劑及/或待黏結材料，諸如木片、木屑、木薄片、木板；切碎或層狀之紙及紙板；砂、蛭石、黏土、水泥及其他矽酸鹽；磨碎膠粉、磨碎熱塑性塑料、磨碎熱固性材料；任何材料(例如紙板、鋁、木及塑料)之蜂窩構造；金屬顆粒及金屬板；顆粒狀或層狀軟木；天然纖維，例如亞麻、大麻及劍麻纖維；合成纖維，例如聚醯胺、聚烯烴、聚芳醯胺、聚酯及碳纖維；礦物纖維，例如玻璃纖維及岩棉纖維；礦物填料，例如 BaSO4及CaCO3；奈米顆粒，例如黏土、無機氧化物及碳；玻璃珠、磨砂玻璃、空心玻璃珠；發泡或可發泡珠粒；未經處理或經處理之廢棄物，例如碾磨、切碎、碾碎或研磨廢棄物且特定言之係飛灰；編織及非編織織物；及兩種或更多種該等材料之組合。
- 一種進一步固化如請求項8至9及利用如請求項1至7中任一項之方法獲得之包含中間聚異三聚氰酸酯之材料的方法，其中該組合物包含環氧樹脂，該方法包括以下步驟：於至少90℃，較佳至少100℃，更佳至少120℃，最佳等於或至少125℃之高溫下加熱該包含中間聚異三聚氰酸酯之材料持續至少數分鐘至2小時。
- 如請求項10之方法，該方法進一步包括在至少90℃之高溫下加熱該組合物之該步驟之前之以下步驟：另添加較佳選自如請求項7至8中任一項之觸媒化合物中之一或多者之三聚觸媒至該包含中間聚異三聚氰酸酯之材料。
- 如請求項10至11中任一項之方法，該方法進一步包括在至少90℃之高溫下加熱該組合物之該步驟之前的以下步驟：在將三聚觸媒化合物與該聚異氰酸酯組合物組合及混合之該步驟之前，添加及混合添加劑及/或一或多種待黏結材料至該包含中間聚異三聚氰酸酯之材料，諸如木片、木屑、木薄片、木板；切碎或層狀之紙及紙板；砂、蛭石、黏土、水泥及其他矽酸鹽；磨碎膠粉、磨碎熱塑性塑料、磨碎熱固性材料；任何材料(例如紙板、鋁、木及塑料)之蜂窩構造；金屬顆粒及金屬板；顆粒狀或層狀軟木；天然纖維，例如亞麻、大麻及劍麻纖維；合成纖維，例如聚醯胺、聚烯烴、聚芳醯胺、聚酯及碳纖維；礦物纖維，例如玻璃纖維及岩棉纖維；礦物填料，例如BaSO4及CaCO3；奈米顆粒，例如黏土、無機氧化物及碳；玻璃珠、磨砂玻璃、空心 玻璃珠；發泡或可發泡珠粒；未經處理或經處理之廢棄物，例如碾磨、切碎、碾碎或研磨廢棄物且特定言之係飛灰；編織及非編織織物；及兩種或更多種該等材料之組合。
- 如請求項10至11中任一項之方法，其進一步包括後固化步驟。
- 一種可依照如請求項10至13中任一項之方法獲得之包含聚異三聚氰酸酯之材料。
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2938666A1 (en) * | 2014-02-04 | 2015-08-13 | Atlas Roofing Corporation | Thermally stable rigid foams and methods of making same |
| DE102015105053A1 (de) * | 2015-04-01 | 2016-10-06 | Airbus Operations Gmbh | Verfahren zum Verarbeiten eines Bauteils, Bauteil, Bauteileinheit und beschichtetes Bauteil |
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| CA2989365C (en) * | 2015-06-18 | 2023-06-27 | Huntsman International Llc | In-situ formation of polyurethane catalysts |
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| EP3381962A1 (de) * | 2017-03-29 | 2018-10-03 | Covestro Deutschland AG | Erzeugung von polyisocyanuratschichten durch getrennte auftragung von isocyanatkomponenten und katalysatoren |
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| US11702499B2 (en) | 2018-12-11 | 2023-07-18 | Trimer Technologies Llc | Polyisocyanurate based polymers and fiber reinforced composites |
| 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 |
| MX2022004946A (es) * | 2019-10-22 | 2022-07-13 | Trimer Tech Llc | Fabricacion de materiales compuestos reforzados con fibra con una resina de isocianato. |
| US11453739B2 (en) * | 2020-06-16 | 2022-09-27 | Covestro Llc | Use of thermally decomposable acid as inhibitor for preparing polyisocyanurate composites |
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Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1212546B (de) * | 1962-06-05 | 1966-03-17 | Bayer Ag | Verfahren zur Polymerisation von aromatischen Polyisocyanaten |
| US3489696A (en) * | 1966-10-06 | 1970-01-13 | Mobay Chemical Corp | Process of preparing polyimides from isocyanates and polycarboxylic acids |
| GB1192859A (en) * | 1967-12-28 | 1970-05-20 | Takeda Chemical Industries Ltd | A Stabilised Isocyanate Composition |
| DE2403858A1 (de) | 1974-01-28 | 1975-08-21 | Basf Ag | Stabile, fluessige amid- und/oder acylharnstoffgruppenhaltige isocyanurat-polyisocyanatloesungen |
| JPS5214692A (en) * | 1975-07-25 | 1977-02-03 | Mitsui Toatsu Chem Inc | Process for preparing an organic isocyanate polymer |
| DE2712931A1 (de) | 1977-03-24 | 1978-09-28 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen |
| JPS53118498A (en) * | 1977-03-25 | 1978-10-16 | Mitsui Toatsu Chem Inc | One-can polyurethane composition |
| US4284730A (en) | 1980-02-07 | 1981-08-18 | Basf Wyandotte Corporation | Liquid carbodiimide- and uretonimine-isocyanurate-containing polyisocyanate compositions and microcellular foams made therefrom |
| JPS58145721A (ja) * | 1982-02-24 | 1983-08-30 | Hitachi Ltd | 樹脂組成物の硬化方法 |
| FR2522667A1 (fr) | 1982-03-04 | 1983-09-09 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
| FR2579205B1 (fr) | 1985-03-25 | 1987-05-15 | Rhone Poulenc Spec Chim | Procede de preparation de polyisocyanates polyisocyanurates par cyclotrimerisation catalytique de polyisocyanates |
| DE3627078A1 (de) * | 1986-08-09 | 1988-02-18 | Bayer Ag | Verfahren zur herstellung von formkoerpern auf polyurethan- und/oder polyharnstoff-basis und die nach diesem verfahren erhaltenen formkoerper |
| US4743627A (en) | 1987-09-14 | 1988-05-10 | Basf Corporation | Liquid isocyanurate-modified polymethylene bis(phenylisocyanate) compositions containing a high two-ring methylene bis(phenylisocyanate) content |
| JPH02110123A (ja) | 1988-10-19 | 1990-04-23 | Asahi Chem Ind Co Ltd | ポリイソシアナートの製法 |
| DE3942890A1 (de) * | 1989-12-23 | 1991-06-27 | Bayer Ag | Verfahren zur herstellung von kunststoff-formteilen |
| AU645290B2 (en) | 1990-03-07 | 1994-01-13 | Huntsman Ici Chemicals Llc | Polyisocyanate composition |
| DE4026474A1 (de) | 1990-08-22 | 1992-02-27 | Bayer Ag | Neue isocyanuratgruppen aufweisende polyisocyanatmischungen, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethanschaumstoffen |
| US5223551A (en) * | 1991-12-26 | 1993-06-29 | Uop | Urea-modified isocyanurates and method of making rigid foams thereof |
| US5221743A (en) | 1992-03-02 | 1993-06-22 | Olin Corporation | Process for producing isocyanurates by cyclotrimerizing isocyanates using polymer-bound catalysts |
| DE4229183A1 (de) | 1992-09-02 | 1994-03-03 | Basf Ag | Verfahren zur Herstellung von niedrigviskosen Isocyanurat- und Urethangruppen enthaltenden Polyisocyanatmischungen |
| US5817732A (en) | 1993-02-12 | 1998-10-06 | Asahi Kasei Kogyo Kabushiki Kaisha | Blocked polyisocyanate and coating composition |
| US5955609A (en) | 1997-12-31 | 1999-09-21 | Bayer Corporation | Trimer catalyst system for aliphatic and aromatic isocyanates |
| DE10110437A1 (de) | 2001-03-05 | 2002-09-19 | Bayer Ag | Verfahren zur Herstellung von Polyisocyanaten durch Umsetzung von Carbonsäuren mit Isocyanaten, die nach diesem Verfahren hergestellten Produkte und deren Verwendung in Polyurethankunststoffen |
| DE10309432A1 (de) | 2003-03-05 | 2004-09-16 | Degussa Ag | Verfahren zur Herstellung von geruchsarmen und lagerstabilen monomerhaltigen Polyisocyanuraten auf Basis von Isophorondiisocyanat |
| US7553963B2 (en) | 2003-10-29 | 2009-06-30 | Bayer Materialscience Llc | Liquid partially trimerized and allophanized polyisocyanates based on toluene diisocyanate and diphenylmethane diisocyanate |
| DE602006018974D1 (de) * | 2005-10-13 | 2011-01-27 | Huntsman Int Llc | Verfahren zur herstellung eines polyisocyanuratpolyurethanmaterials |
| EP1940899B1 (en) * | 2005-10-13 | 2009-08-05 | Huntsman International Llc | Process for preparing polyisocyanurate polyurethane material |
| CN101466517B (zh) * | 2006-06-14 | 2012-02-22 | 亨茨曼国际有限公司 | 复合面板 |
| WO2008068198A1 (de) | 2006-12-04 | 2008-06-12 | Basf Se | Verfahren zur herstellung von polyisocyanaten |
| HUE041930T2 (hu) | 2007-03-27 | 2019-06-28 | Basf Se | Eljárás diizocianátok színtelen izocianurátjainak elõállítására |
| EP2342252B1 (en) | 2008-08-28 | 2017-04-26 | Huntsman International LLC | Mixture obtained by reacting polyol and anhydride and it's use in polyisocyanates for making polyisocyanurates |
| CN102405244B (zh) * | 2009-04-21 | 2016-10-05 | 亨茨曼国际有限公司 | 多异氰酸酯组合物 |
| BR112013016686B1 (pt) * | 2011-01-31 | 2020-07-07 | Huntsman International Llc | composição de resina epóxi, processo para a preparação de uma composição, composição curável, material de poliisocianurato-poliuretano, processo para fabricar um material de poliisocianurato- poliuretano, e, uso de um composto |
| EP2644270A1 (en) * | 2012-03-29 | 2013-10-02 | Huntsman International Llc | Polyisocyanate trimerization catalyst composition |
-
2012
- 2012-07-17 EP EP12176644.8A patent/EP2687551A1/en not_active Ceased
-
2013
- 2013-06-14 TW TW102121226A patent/TW201404792A/zh unknown
- 2013-06-18 EP EP13730231.1A patent/EP2875059B1/en active Active
- 2013-06-18 WO PCT/EP2013/062597 patent/WO2014012728A1/en not_active Ceased
- 2013-06-18 PL PL13730231T patent/PL2875059T3/pl unknown
- 2013-06-18 JP JP2015522010A patent/JP2015528039A/ja active Pending
- 2013-06-18 IN IN31DEN2015 patent/IN2015DN00031A/en unknown
- 2013-06-18 US US14/413,459 patent/US9631043B2/en active Active
- 2013-06-18 CA CA2878797A patent/CA2878797C/en active Active
- 2013-06-18 MX MX2015000620A patent/MX369050B/es active IP Right Grant
- 2013-06-18 KR KR1020157000881A patent/KR102005824B1/ko not_active Expired - Fee Related
- 2013-06-18 RU RU2015105176A patent/RU2628086C2/ru active
- 2013-06-18 CN CN201380038054.0A patent/CN104640892B/zh active Active
- 2013-06-18 BR BR112015001029-6A patent/BR112015001029B1/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP2875059B1 (en) | 2021-01-06 |
| CA2878797A1 (en) | 2014-01-23 |
| US20150158967A1 (en) | 2015-06-11 |
| PL2875059T3 (pl) | 2021-08-23 |
| CA2878797C (en) | 2017-07-04 |
| WO2014012728A1 (en) | 2014-01-23 |
| IN2015DN00031A (zh) | 2015-05-22 |
| MX369050B (es) | 2019-10-28 |
| MX2015000620A (es) | 2015-04-14 |
| EP2687551A1 (en) | 2014-01-22 |
| US9631043B2 (en) | 2017-04-25 |
| BR112015001029B1 (pt) | 2021-03-02 |
| CN104640892B (zh) | 2017-07-25 |
| JP2015528039A (ja) | 2015-09-24 |
| BR112015001029A2 (pt) | 2017-06-27 |
| RU2015105176A (ru) | 2016-09-10 |
| KR102005824B1 (ko) | 2019-08-01 |
| KR20150036063A (ko) | 2015-04-07 |
| EP2875059A1 (en) | 2015-05-27 |
| RU2628086C2 (ru) | 2017-08-14 |
| CN104640892A (zh) | 2015-05-20 |
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