CN110498906A - 快速固化型环氧体系 - Google Patents
快速固化型环氧体系 Download PDFInfo
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- CN110498906A CN110498906A CN201910409499.4A CN201910409499A CN110498906A CN 110498906 A CN110498906 A CN 110498906A CN 201910409499 A CN201910409499 A CN 201910409499A CN 110498906 A CN110498906 A CN 110498906A
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- 239000004593 Epoxy Substances 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 49
- -1 cyclic amine Chemical class 0.000 claims abstract description 46
- 125000000962 organic group Chemical group 0.000 claims abstract description 34
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 27
- 239000003822 epoxy resin Substances 0.000 claims abstract description 25
- 150000003839 salts Chemical class 0.000 claims abstract description 18
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 16
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 14
- 239000007848 Bronsted acid Substances 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 61
- 150000001412 amines Chemical class 0.000 claims description 39
- 239000002585 base Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 15
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 11
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 claims description 11
- 229920000768 polyamine Polymers 0.000 claims description 9
- 150000002500 ions Chemical class 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 7
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 239000012752 auxiliary agent Substances 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
- 125000003700 epoxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 229910021645 metal ion Inorganic materials 0.000 claims description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 5
- 150000003053 piperidines Chemical class 0.000 claims description 5
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 claims description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 3
- 230000001070 adhesive effect Effects 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 2
- JJMGBQYNPQTPPB-UHFFFAOYSA-N 2-piperidin-3-ylethanamine Chemical class NCCC1CCCNC1 JJMGBQYNPQTPPB-UHFFFAOYSA-N 0.000 claims description 2
- PXJBCMWIAPDWAU-UHFFFAOYSA-N 2-piperidin-4-ylethanamine Chemical class NCCC1CCNCC1 PXJBCMWIAPDWAU-UHFFFAOYSA-N 0.000 claims description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 2
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- UVLSCMIEPPWCHZ-UHFFFAOYSA-N 3-piperazin-1-ylpropan-1-amine Chemical compound NCCCN1CCNCC1 UVLSCMIEPPWCHZ-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- 150000000918 Europium Chemical class 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 159000000013 aluminium salts Chemical class 0.000 claims 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- 150000001621 bismuth Chemical class 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 229910003002 lithium salt Inorganic materials 0.000 claims 1
- 159000000002 lithium salts Chemical class 0.000 claims 1
- 150000004714 phosphonium salts Chemical class 0.000 claims 1
- 150000003751 zinc Chemical class 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- 150000002118 epoxides Chemical class 0.000 description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 12
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 12
- 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 11
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical group C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- CFSYYJNGCPTQRE-UHFFFAOYSA-N calcium;trifluoromethanesulfonic acid Chemical compound [Ca].OS(=O)(=O)C(F)(F)F CFSYYJNGCPTQRE-UHFFFAOYSA-N 0.000 description 5
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-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
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 150000001537 azepanes Chemical class 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 229960004217 benzyl alcohol Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- SPWBJDZFBWHQGT-UHFFFAOYSA-N europium;trifluoromethanesulfonic acid Chemical compound [Eu].OS(=O)(=O)C(F)(F)F SPWBJDZFBWHQGT-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 3
- 229910001486 lithium perchlorate Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 3
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 2
- PPNCOQHHSGMKGI-UHFFFAOYSA-N 1-cyclononyldiazonane Chemical compound C1CCCCCCCC1N1NCCCCCCC1 PPNCOQHHSGMKGI-UHFFFAOYSA-N 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 2
- JPEGUDKOYOIOOP-UHFFFAOYSA-N 2-(hexoxymethyl)oxirane Chemical compound CCCCCCOCC1CO1 JPEGUDKOYOIOOP-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-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
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 2
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 2
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 125000004442 acylamino group Chemical group 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- OOULUYZFLXDWDQ-UHFFFAOYSA-L barium perchlorate Chemical compound [Ba+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O OOULUYZFLXDWDQ-UHFFFAOYSA-L 0.000 description 2
- UCJNCJZFRKZIHY-UHFFFAOYSA-N barium;trifluoromethanesulfonic acid Chemical compound [Ba].OS(=O)(=O)C(F)(F)F UCJNCJZFRKZIHY-UHFFFAOYSA-N 0.000 description 2
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 description 2
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+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 NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 125000005587 carbonate group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 235000009508 confectionery Nutrition 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- WDGKXRCNMKPDSD-UHFFFAOYSA-N lithium;trifluoromethanesulfonic acid Chemical compound [Li].OS(=O)(=O)C(F)(F)F WDGKXRCNMKPDSD-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N trimethylmethane Natural products CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 2
- UDATXMIGEVPXTR-UHFFFAOYSA-N 1,2,4-triazolidine-3,5-dione Chemical compound O=C1NNC(=O)N1 UDATXMIGEVPXTR-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
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- 239000002994 raw material Substances 0.000 description 1
- AXXFVUWEFGKYBC-UHFFFAOYSA-N samarium;trifluoromethanesulfonic acid Chemical compound [Sm].OS(=O)(=O)C(F)(F)F AXXFVUWEFGKYBC-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
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- HGJLYMGBCAKBLK-UHFFFAOYSA-N sodium;trifluoromethanesulfonic acid Chemical compound [Na].OS(=O)(=O)C(F)(F)F HGJLYMGBCAKBLK-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
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- 150000004886 thiomorpholines Chemical class 0.000 description 1
- CKUBWOWGEBSNBJ-UHFFFAOYSA-N tin;trifluoromethanesulfonic acid Chemical compound [Sn].OS(=O)(=O)C(F)(F)F CKUBWOWGEBSNBJ-UHFFFAOYSA-N 0.000 description 1
- 230000005945 translocation Effects 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- NGOCMUBXJDDBLB-UHFFFAOYSA-N trifluoromethanesulfonic acid;zinc Chemical compound [Zn].OS(=O)(=O)C(F)(F)F NGOCMUBXJDDBLB-UHFFFAOYSA-N 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
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Abstract
本发明涉及快速固化型环氧体系。本发明涉及组合物,其包含a)至少一种环氧树脂,b)至少一种式(I)的环状胺其中‑R1至R4表示H或有机基团,‑X=–(Y1)m‑(A1)n‑(Y2)o‑(A2)p‑(Y3)q‑(A3)r‑(Y4)s–(II)其中彼此独立地‑m、n、o、p、q、r和s=0或1,‑A1、A2、A3=亚烷基或亚烯基,且‑Y1、Y2、Y3、Y4=NR5、PR5、O或S,其中R5彼此独立地=有机基团,‑其中选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的各两个有机基团也可以形成一个或多个其它环,‑条件是,选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的至少一个存在的基团被至少一个基团–NHR6或–NH2取代,其中R6=有机基团,和c)至少一种极强布朗斯台德酸的盐,涉及其制备方法及其用途。
Description
技术领域
本发明的主题是包含至少一种环氧树脂、至少一种环状胺和极强布朗斯台德酸的盐的组合物。
背景技术
环氧树脂,尤其是由双酚A和表氯醇制成的那些,是制备高品质浇注树脂、涂料物料、复合材料和胶粘剂的已知原料。用多胺固化的芳族环氧树脂除了良好的耐化学品性和耐溶剂性外还对许多基底具有良好的粘附强度。
为了加速环氧-胺-涂料体系的固化,可以使用催化剂(US 3,492,269 A、US 5,470,896 A、GB 1,105,772 A)。
EP 0 083 813 A1、EP 2 957 584 A1、US 5,441,000 A、US 5,629,380 A、WO 96/09352 A1公开了用不同的胺进行环氧树脂的催化固化。
环状胺在环氧固化中表现出优点。US 8,951,619 B2和US 9,006,385 B2尤其公开了用N-取代的哌嗪进行环氧树脂的无催化剂的固化。
CN 106905816 A、CN 106833261 A、JP H08-113876 A、DE 1 954 701 A1、CA 2165 585 A1和US 3,055,901 A公开了用氨基乙基哌嗪进行环氧树脂的无催化剂的固化。
US 8,980,979 B2公开了任选地在催化剂存在下用尤其是环状二胺进行环氧树脂的固化,该环状二胺选自哌嗪或高哌嗪。
EP 0 969 030 A1公开了环氧/胺-涂料体系,其胺组分是脂族胺。该组合物可以具有催化剂。在实施例中,使用氨基乙基哌嗪作为固化剂。
US 4,775,734 A公开了在使用催化量的不同的胺的四氟硼酸盐或六氟磷酸盐的情况下用氨基乙基哌嗪进行环氧树脂的固化。对比例(实施例2)中此外公开了在四氟硼酸锂存在下用氨基乙基哌嗪进行环氧树脂的固化的实验。然而,在使用的环氧基团:NH基团的比率下,没有进行反应。此外,在对比例(实施例9)中,将环氧树脂在咪唑啉存在下用氨基乙基哌嗪进行固化。然而,所用的咪唑啉的缺点是,在潮湿材料存在下它不是储存稳定的并且易于变黄。
EP 3 255 078 A1公开了包含至少一种环氧化合物、2-(2,2,6,6-四甲基哌啶-4-基)丙烷-1,3-二胺和任选催化剂的环氧树脂组合物,所述催化剂尤其可以是无机盐。
WO 2017/074810 A1公开了包含环氧树脂、聚醚胺和另一种胺固化剂以及金属三氟甲磺酸盐-催化剂的组合物,该胺固化剂尤其可以是一种咪唑或咪唑啉。
现有技术中的组合物的共同之处是,它们固化过慢或仅在高温下固化。
然而,对于许多应用而言重要的是,表面固化或完全彻底固化特别快速地进行或在低温下进行。前者可以提高生产率,或加速下一个加工步骤。后者尤其在寒冷地区中是重要的,以例如为船只或管道提供防腐蚀涂层,以使得在那里在冬季也可以进一步操作。
发明内容
因此,本文的目的是提供环氧体系,其在相同的条件下比迄今已知的配制品明显更快地反应。另一个目的是提供环氧配制品,其在明显低于室温的温度下比迄今可能更快地部分固化或完全固化(an- bzw. aushärten)。
本文提出的目的通过根据本发明的组合物得以实现,所述组合物包含
a) 至少一种环氧树脂,
b) 至少一种式(I)的环状胺
其中
- R1至R4表示H或有机基团,且
- X = –(Y1)m-(A1)n-(Y2)o-(A2)p-(Y3)q-(A3)r-(Y4)s– (II)
其中彼此独立地
◦ m、n、o、p、q、r和s = 0或1,
◦ A1、A2、A3 = 亚烷基或亚烯基,且
◦ Y1、Y2、Y3、Y4 = NR5、PR5、O或S,其中R5彼此独立地= 有机基团,
◦ 其中选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的各两个有机基团也可以形成一个或多个其它环,
- 条件是,选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的至少一个存在的基团被至少一个基团–NHR6或–NH2取代,其中R6 = 有机基团,和
c) 至少一种极强布朗斯台德酸的盐,其具有选自金属离子、含金属的离子、鏻离子和未取代的铵离子的反荷离子。
所述环氧树脂的环氧基团与所有胺的所有NH基团的总和的比率为0.5 : 1至1.5 :1,优选0.8 : 1至1.2 : 1,非常特别优选0.9 : 1至1.1 : 1。“所有胺”在此应被理解为是指式(I)的环状胺以及下面描述的不包括在式(I)下的胺d)。相应的反应具有优点,即由此增加交联密度和摩尔质量,并因此改进机械性能、耐化学品性和耐刮擦性。此外,没有未反应的成分剩余在涂层中,该未反应的成分可能会进入不希望的副反应,从涂层中迁移出来或至少作为增塑剂降低热变形耐受性。
组分a)是至少一种环氧树脂。原则上,所有环氧化合物都适用于此。
合适的环氧化合物例如描述在EP 675 185 A2中。可以考虑多种已知化合物,其每分子含有多于一个环氧基团,优选两个环氧基团。这些环氧化合物在此既可以是饱和的也可以是不饱和的,以及可以是脂族、脂环族、芳族或杂环的,并且还可以具有羟基。它们此外可以含有在混合-或反应条件下不引起干扰性副反应的那些取代基,例如烷基-或芳基取代基或醚基团。
优选的环氧化合物在此是缩水甘油醚,其衍生自多元酚,特别是双酚以及酚醛清漆,并且其基于环氧基团的数量计的摩尔质量ME(“环氧当量重量”,“EV值”)为100至1500g/val,但特别是150至250 g/val。
特别优选的环氧化合物衍生自间苯二酚,对苯二酚,2,2-双-(4-羟基苯基)-丙烷(双酚A),二羟基二苯基甲烷的异构体混合物(双酚F),4,4'-二羟基二苯基环己烷,4,4'-二羟基-3,3'-二甲基二苯基丙烷,4,4'-二羟基联苯,4,4'-二羟基二苯甲酮,双-(4-羟基苯基)-1,1-乙烷,双-(4-羟基苯基)-1,1-异丁烷,2,2-双-(4-羟基-叔丁基苯基)-丙烷,双-(2-羟基萘基)-甲烷,1,5-二羟基萘,三-(4-羟基苯基)甲烷,双-(4-羟基苯基)醚,双-(4-羟基苯基)砜,以及上述化合物的氯化-和溴化产物(例如四溴双酚A)。
非常特别优选地,使用基于双酚A和双酚F的液体二缩水甘油醚,其环氧当量重量为150至200 g/val。
优选地,也可以使用多元醇的多缩水甘油醚,例如乙二醇-1,2-二缩水甘油醚、丙二醇-1,2-二缩水甘油醚、丙二醇-1,3-二缩水甘油醚、丁二醇二缩水甘油醚、戊二醇二缩水甘油醚(也称为新戊二醇二缩水甘油醚)、己二醇二缩水甘油醚、二乙二醇二缩水甘油醚、二丙二醇二缩水甘油醚、更高级的聚氧亚烷基二醇二缩水甘油醚,例如更高级的聚氧亚乙基二醇二缩水甘油醚和二醇二缩水甘油醚、混合聚氧亚乙基-亚丙基二醇二缩水甘油醚、聚氧四亚甲基二醇二缩水甘油醚、甘油的多缩水甘油醚、1,2,6-己三醇的多缩水甘油醚、三羟甲基丙烷的多缩水甘油醚、三羟甲基乙烷的多缩水甘油醚、季戊四醇的多缩水甘油醚、山梨糖醇的多缩水甘油醚、烷氧基化多元醇(例如甘油、三羟甲基丙烷、季戊四醇等)的多缩水甘油醚、环己烷二甲醇的二缩水甘油醚、双-(4-羟基环己基)甲烷的二缩水甘油醚和2,2-双-(4-羟基环己基) 丙烷的二缩水甘油醚、蓖麻油的多缩水甘油醚、三-(2-羟基-乙基)异氰脲酸三缩水甘油酯。此外可考虑优选作为组分A) 的是:聚-(N-缩水甘油基)化合物,其可通过表氯醇和胺的反应产物的脱卤化氢来获得,所述胺如苯胺、正丁基胺、双-(4-氨基苯基)甲烷、间-苯二甲胺或双-(4-甲基氨基苯基)甲烷。但是,聚-(N-缩水甘油基)化合物也包括异氰脲酸三缩水甘油酯、三缩水甘油基尿唑及其低聚物、环亚烷基脲的N,N’-二缩水甘油基衍生物和乙内酰脲的二缩水甘油基衍生物。
此外,也可以优选使用多羧酸的多缩水甘油酯,其通过表氯醇或类似的环氧化合物与脂族、脂环族或芳族多羧酸如草酸、琥珀酸、己二酸、戊二酸、邻苯二甲酸、对苯二甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸、2,6-萘二甲酸和更高级的二羧酸二缩水甘油酯,例如二聚或三聚的亚麻酸的反应来获得。实例是己二酸二缩水甘油酯、邻苯二甲酸二缩水甘油酯和六氢邻苯二甲酸二缩水甘油酯。
此外可优选提及不饱和羧酸的缩水甘油酯和不饱和醇或不饱和羧酸的环氧化酯。除了多缩水甘油醚外,可以以基于多缩水甘油醚的质量计最多30重量%,优选10至20重量%的质量比例一起使用少量的单环氧化物例如甲基缩水甘油醚,丁基缩水甘油醚,烯丙基缩水甘油醚,乙基己基缩水甘油醚,长链脂族缩水甘油醚,例如鲸蜡基缩水甘油醚和硬脂基缩水甘油醚,更高级的异构的醇混合物的单缩水甘油醚,C12至C13醇的混合物的缩水甘油醚,苯基缩水甘油醚,甲苯基缩水甘油醚,对叔丁基苯基缩水甘油醚,对辛基苯基缩水甘油醚,对苯基-苯基缩水甘油醚,烷氧基化(oxalkylierten)月桂醇的缩水甘油醚以及单环氧化物例如环氧化单不饱和烃(氧化丁烯、-环己烯、-苯乙烯)。
合适的环氧化合物的详细列举可以在A. M. Paquin的手册"Epoxidverbindungenund Epoxidharze",Springer Verlag,Berlin,1958,第IV章中和在Lee Neville "Handbook of Epoxy Resins",1967,第2章中找到。
在此可以优选考虑缩水甘油醚和缩水甘油酯、脂族环氧化物、基于双酚A和/或双酚F的二缩水甘油醚和甲基丙烯酸缩水甘油酯作为环氧化合物。这种环氧化物的实例还有异氰脲酸三缩水甘油酯(TGIC,商品名ARALDIT 810,Huntsman)、对苯二甲酸二缩水甘油酯和偏苯三酸三缩水甘油酯的混合物(商品名ARALDIT PT 910和912,Huntsman)、叔碳酸(Versaticsäure)的缩水甘油酯(商品名CARDURA E10,Shell)、3’,4’-环氧环己烷甲酸-3,4-环氧环己基甲酯(ECC)、乙基己基缩水甘油醚、丁基缩水甘油醚、季戊四醇四缩水甘油醚,(商品名POLYPOX R 16,UPPC AG)以及具有游离环氧基团的其它Polypox类型。
也可以使用所提及的环氧化合物的混合物。
特别优选的环氧树脂是基于双酚A-二缩水甘油醚、双酚F-二缩水甘油醚、4,4'-亚甲基-双[N,N-双(2,3-环氧丙基)苯胺]、己二醇二缩水甘油醚、丁二醇二缩水甘油醚、三羟甲基丙烷三缩水甘油醚、1,2,3-丙三醇三缩水甘油醚、季戊四醇四缩水甘油醚和六氢邻苯二甲酸二缩水甘油酯的多环氧化物。
优选使用上述环氧化合物的混合物作为组分A)。
作为环状胺b),原则上可以考虑具有刚好一个环的,即环上的,NH基团作为NH载体以及至少一个非环上的伯或仲氨基的所有化合物。然而此外,根据本发明使用的胺当然还可以具有非反应性的叔氨基。
胺b)具有式(I)
其中
- R1至R4表示H或有机基团,且
- X = –(Y1)m-(A1)n-(Y2)o-(A2)p-(Y3)q-(A3)r-(Y4)s– (II)
其中彼此独立地
- m、n、o、p、q、r和s = 0或1,
- A1、A2、A3 = 亚烷基或亚烯基,且
- Y1、Y2、Y3、Y4 = NR5、PR5、O或S,其中R5 = 有机基团,
- 其中选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的各两个有机基团也可以形成一个或多个其它环,
条件是,选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的至少一个存在的基团被至少一个基团–NHR6或–NH2取代,其中R6 = 有机基团。
关于在式(I)中所示的环,该环状胺是饱和或部分不饱和的。相应的胺比相应的芳族胺和咪唑啉更快地反应。在环状胺中任选存在的其它环不仅可以是饱和或不饱和的,而且还可以是芳族的。
关于在式(I)中所示的环,优选的环状胺是饱和的。
优选地,基团R1、R2、R3和R4中的至少一个 = H。由于基团R1、R2、R3和R4中的至少一个= H,因此与环上的氨基相邻的碳原子在总体上在至少一个位置处是未取代的。相应的胺比其中所有四个基团R1、R2、R3和R4 ≠ H的胺反应更快。更优选地,基团R1、R2、R3和R4中的至少两个,更优选至少三个,非常特别优选所有 = H。
在基团X中,如果存在,A1、A2和A3彼此独立地是亚烷基或亚烯基。它们又可以带有有机基团。如果亚烷基和/或亚烯基本身具有一个或多个有机基团,则选自亚烷基和/或亚烯基的有机基团的各两个有机基团也可以相互或与任选存在的有机基团R1至R5形成一个或多个其它环。
优选地,如果存在,A1、A2和A3各自彼此独立地具有式(III),
-(CR7R8)x-(CR9=CR10)y-(CR11R12)z- (III)
其中彼此独立地
- R7、R8、R9、R10、R11和R12 = H或有机基团,且
- 1 ≤ x + y + z ≤ 7。
指数x、y和z可以相应于它们所属的基团A1、A2和A3优选也被称为指数x1、y1和z1,x2、y2和z2和x3、y3和z3。
优选地,X具有2至15个原子的链长。因此,优选地,所有x、½•y和z以及m、o、q和s的总和是2至15的值,更优选2至8的值,还更优选2至5的值,并且非常特别优选2至4的值。换句话说,优选的是2 ≤ m + o + q + s + x1 + ½•y1 + z1 + x2 + ½•y2 + z2 + x3 + ½•y3 +z3 ≤ 15。更优选的是2 ≤ m + o + q + s + x1 + ½•y1 + z1 + x2 + ½•y2 + z2 + x3 +½•y3 + z3 ≤ 8,更优选2 ≤ m + o + q + s + x1 + ½•y1 + z1 + x2 + ½•y2 + z2 + x3 +½•y3 + z3 ≤ 5,非常特别优选2 ≤ m + o + q + s + x1 + ½•y1 + z1 + x2 + ½•y2 + z2+ x3 + ½•y3 + z3 ≤ 4。
式(I)的胺是(任选双-/多)环状化合物,因为与氨基相邻的两个碳原子在两侧与式(II)的取代的(杂)亚烷基连接。
更优选地,式(I)除了环上的NH基团的氮原子而外还在该环中具有最多一个另外的杂原子,即X优选具有式(IIa)
X = –(CR7R8)x-(Y)o-(CR11R12)z– (IIa)
其中
- x和z = 0、1、2、3、4、5、6或7,
- o = 0或1,
- 2 ≤ x + o + z ≤ 15
- R7、R8、R11、R12 = H或有机基团,且
- Y = NR5、PR5、O或S,其中R5 = 有机基团。
此时相应适用的是,在式(I)中选自R1至R8、R11和R12的各两个有机基团也可以形成一个或多个其它环,条件是,选自R1至R8、R11和R12的至少一个存在的基团被至少一个基团–NHR6或–NH2取代,其中R6 =有机基团。
在x = 2 – 4且o和z = 0的优选情况下,所产生的化合物是具有一个NH基团的饱和杂烷基-环体系。优选的化合物是吡咯烷类、哌啶类和氮杂环庚烷类。在x = 1 – 3,o = 1且z = 0 – 2的优选情况下是在环中具有一个NH基团和另一个杂原子(其不是另一个环NH基团的一部分)的饱和杂烷基-环体系。优选的化合物是单N-取代的吡唑烷、单N-取代的咪唑烷、噁唑烷、噻唑烷、单N-取代的哌嗪、吗啉类、硫代吗啉类、单N-取代的二氮杂环庚烷、氧杂氮杂环庚烷类和硫杂氮杂环庚烷类。因此,优选的是在式(IIa)中,x = 1 – 4,o = 0或1且z = 0 – 2。
但是,也可以使用在环中具有三个杂原子的化合物。特别优选的是三氮杂环己烷类和三氮杂环庚烷类的组。特别地,这些化合物可以桥接存在,例如在非常特别优选的1,3,6-三氮杂双环[4.2.1]壬烷类的化合物的组的情况中。
基团R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11和R12可以是有机基团。优选的有机基团是烷基、烯基、炔基、芳基或芳烷基。它们可以在其链内是杂原子取代的和/或带有取代基。优选的有机基团是烷基、烯基、炔基、芳基或芳烷基,其在链内可以带有一个或多个醚基、羧基、氨基、酰氨基、脲基、氨基甲酸酯基、碳酸酯基、脒基或胍基。此外, 优选的有机基团可以带有一个或多个选自有机基团的取代基,任选具有醚基、羧基、氨基、酰氨基、脲基、氨基甲酸酯基、碳酸酯基、脒基或胍基,其任选地也可以被羟基、腈基或卤素基团取代或本身是羟基、腈基或卤素基团。
优选的式(I)的化合物是氨基乙基哌嗪(AEP,1-(2-氨基乙基)哌嗪)、1-(3-氨基丙基)哌嗪、1-咪唑烷乙胺、咪唑烷-N-丙胺、α-甲基-1-哌嗪乙胺、2,6-二甲基-1-哌嗪乙胺、2-氨基-1-(哌嗪-1-基)乙酮、4-(2-氨基乙基)哌啶、3-(2-氨基乙基)哌啶和2-(2-氨基乙基))哌啶。
式(I)的化合物也可以以混合物形式来使用。
根据本发明的组合物此外包含至少一种极强布朗斯台德酸的盐,其具有选自金属离子、含金属的离子、鏻离子和未取代的铵离子的反荷离子。相应的盐用作催化剂。在此,应将这种极强酸理解为是指其pKa值(或在多质子酸的情况下,其第一质子转移阶段的pKa值)小于或等于-9.01的酸。优选地,所述极强酸的pKa值为-9.5至-25,特别优选-9.9至-21。
pKa被定义为平衡常数Ka的负十进制对数,并且被认为是酸的强度的量度。pKa值越小,酸就越强。pKa值如F.G. Bordwell, “Equilibrium Acidities inDimethylsulfoxide Solution“, Acc. Chem. Res. 1988, 21, 456-463中公开的那样来确定。
优选的盐是在下表1中在第一栏中总结的极强酸的相应盐:
表1:
酸 | pK<sub>a</sub>值 | 文献位置,如果没有在Bordwell中公开 |
高氯酸 | -10 | 1 |
三氟甲磺酸 | -14 | |
氢碘酸 | -9,5 | 2 |
六氟磷酸 | -10 | 3 |
六氟锑酸 | -17 | 3 |
1) Hollemann Wiberg, Lehrbuch der anorganischen Chemie, 第91.-100版,Walter der Gruyter Verlag, Berlin, New York, 1985, 第428页.
2) Journal of Physical Chemistry A, Volume 120, Issue 20, 第3663-3669页.
3)
=acid。
这些极强酸的反荷离子选自金属离子、含金属的离子、鏻离子和未取代的铵离子。优选的金属离子是碱土金属阳离子,特别是铍-、镁-、钙-、锶-和钡-离子,以及锂-、铝-、铋-、锌-和铕离子。
含金属的离子是含有至少一种金属但不是纯金属离子的离子。它们优选是金属化合物离子,例如四苯基锑离子。
所述反荷离子也可以是铵离子(NH4 +)或任选烷基化和/或芳基化的鏻离子。非常特别优选的是铵离子。
优选的极强酸的盐是三氟甲磺酸钙、三氟甲磺酸铕、三氟甲磺酸钡、三氟甲磺酸铝、三氟甲磺酸铋、三氟甲磺酸锂、高氯酸锂、高氯酸钡、六氟磷酸锂和高氯酸锌。非常特别优选的是三氟甲磺酸钙、三氟甲磺酸铕、六氟磷酸锂和高氯酸锂。
优选是在有机介质(例如苄醇)中良好溶解的盐,即在20℃下在苄醇中溶解度为至少10 g/l的盐。
优选地,根据本发明的组合物此外可以具有d)不包括在式(I)下的胺和/或e)其它助剂或添加剂。
不包括在式(I)下的胺d)优选是二胺或多胺。它们可以是单体的、低聚的和/或聚合的化合物。优选的单体的和低聚的化合物选自二胺、三胺和四胺。二胺或多胺d)的胺基可以与伯、仲或叔碳原子连接,优选与伯或仲碳原子连接。也可以使用二胺和/或多胺的混合物作为组分d)。
作为组分d),优选可以单独或以混合物形式使用下列胺:
• 脂族胺,特别是多亚烷基多胺,其优选选自1,2-乙二胺、1,2-丙二胺、1,3-丙二胺、1,2-丁二胺、1,3-丁二胺、1,4-丁二胺、2-(乙基氨基)乙胺、3-(甲基氨基)丙胺、二亚乙基三胺、三亚乙基四胺、五亚乙基六胺、三甲基六亚甲基二胺、2,2,4-三甲基六亚甲基二胺、2,4,4-三甲基六亚甲基二胺、2-甲基-戊二胺、六亚甲基二胺、N-(2-氨基乙基)-1,2-乙二胺、N-(3-氨基丙基)-1,3-丙二胺、N,N"-1,2-乙二基双-(1,3-丙二胺)、二亚丙基三胺、己二酸二酰肼和肼;
• 氧化烯多胺,其优选选自聚氧亚丙基二胺和聚氧亚丙基三胺(例如Jeffamine® D-230、Jeffamine® D-400、Jeffamine® T-403、Jeffamine® T-5000)、1,13-二氨基-4,7,10-三氧杂十三烷、4,7-二氧杂癸烷-1,10-二胺;
• 脂环族胺,其优选选自异佛尔酮二胺(3,5,5-三甲基-3-氨基甲基-环己胺),单独或以异构体混合物形式的4,4'-二氨基二环己基甲烷、2,4'-二氨基二环己基甲烷和2,2'-二氨基二环己基甲烷,3,3'-二甲基-4,4'-二氨基-二环己基甲烷、N-环己基-1.3-丙二胺、1,2-二氨基环己烷、3-(环己基氨基)丙胺、TCD-二胺(3(4), 8(9)-双(氨基甲基)三环[5.2.1.02,6]癸烷)、4-甲基环己烷-1,3-二胺
• 芳脂族胺,优选苯二甲胺;
• 芳族胺,优选苯二胺,特别是1,3-苯二胺和1,4-苯二胺,和任选地单独或以异构体混合物形式的4,4'-二氨基二苯基甲烷、2,4'-二氨基二苯基甲烷、2,2'-二氨基二苯基甲烷;
• 加成固化剂,特别是环氧化合物,特别是双酚A和F的缩水甘油醚与过量胺的反应产物;
• 聚酰胺基胺固化剂,特别是通过单-和多羧酸与多胺的缩合获得的聚酰胺基胺固化剂,非常特别是通过二聚脂肪酸与多亚烷基多胺的缩合;
• 曼尼希碱固化剂,特别是通过一元或多元酚与醛,特别是甲醛,和多胺的反应,曼尼希碱固化剂;和
• 曼尼希碱,特别是基于苯酚和/或间苯二酚,甲醛和间苯二甲胺以及N-氨基乙基哌嗪和下述的共混物:N-氨基乙基哌嗪与壬基苯酚和/或苄醇,腰果壳油酚醛胺(Phenalkamine),其由腰果酚、醛和胺在曼尼希反应中获得。
也可以使用上述二胺和多胺的混合物作为组分d)。
优选的其它助剂和添加剂e)可以是环氧化学中常用的化合物。优选的助剂和添加剂e)是颜料、溶剂、流平剂、改性剂,例如苄醇或壬基苯酚,脱气剂、消光剂、反应性稀释剂,以及常规催化剂,如水杨酸、双酚A、2,4,6-三(二甲基氨基甲基)苯酚和苯酚衍生物。
在一个优选的实施方案中,不使用其它不包括在式(I)下的胺d)。在一个优选的实施方案中,不使用其它常规催化剂,即可能的助剂和添加剂限于颜料、溶剂、流平剂、改性剂、脱气剂、消光剂和反应性稀释剂。
在根据本发明的组合物中的组分a)至e)的组成优选为下列重量百分比例,基于组合物的总质量计:
a) 环氧树脂 30 – 95 %
b) 环状胺 1 – 50 %
c) 极强布朗斯台德酸的盐 0.001 – 5 %,
优选0.1 – 3 %,
d) 其它胺 0 – 48 %和
e) 其它助剂或添加剂0 – 48 %。
此外优选地,胺b)的重量百分比例基于胺b)和d)的总质量计为至少10重量%,特别优选至少30%,非常特别优选至少50%,还更优选至少70%。
此外,本发明的主题是制备根据本发明的组合物的方法,其中将至少一种环氧树脂a)、至少一种环状胺b)和至少一种极强酸的盐c)相互混合。
此外,本发明的主题是根据本发明的组合物作为浇铸树脂、涂料物料、复合材料或胶粘剂或作为它们的组成部分的用途。
具体实施方式
实验部分:
实施例1)
为了证明所要求保护的催化剂的特别的反应性,首先将模型实验相互比较。为此,各自将0.025摩尔(3.75g)1,2-环氧-3-苯氧基丙烷加入到22.68g甲苯(溶剂)和2.08g 十四烷(内标)的混合物中。此外,加入0.025摩尔(2.13g)的哌啶和0.06g各自的催化剂。在混合之后立即进行GC并且将1,2-环氧-3-苯氧基丙烷的含量与十四烷的含量比较。在室温下4小时后,借助于GC检测测定1,2-环氧-3-苯氧基丙烷(EP)的残余含量(通过内标十四烷校准)。由此产生以下结果:
催化剂的比较
催化剂 | 0样品中的% EP | 在室温下4小时后的% EP | |
1* | 无催化剂 | 97 | 93 |
2* | 二月桂酸二丁基锡 | 99 | 93 |
3* | 二氮杂双环壬烷 (DBN) | 97 | 95 |
4* | 二氮杂双环十一烷 (DBU) | 96 | 93 |
5* | 二氮杂双环辛烷 (DABCO) | 94 | 93 |
6* | 乙酰丙酮锌 | 94 | 90 |
7* | 三溴化四丁基铵 | 91 | 87 |
8* | 新癸酸铋 | 91 | 88 |
9* | 四丁醇钛 | 95 | 94 |
10* | 水杨酸 | 93 | 90 |
11* | 苯酚 | 97 | 85 |
12 | 三氟甲磺酸钙 | 90 | 0 |
13 | 三氟甲磺酸铋 | 90 | 57 |
14 | 三氟甲磺酸钠 | 96 | 52 |
15 | 三氟甲磺酸铕 | 85 | 16 |
16 | 三氟甲磺酸钡 | 96 | 37 |
17 | 三氟甲磺酸铝 | 98 | 53 |
18 | 三氟甲磺酸锂 | 90 | 28 |
19 | 高氯酸锂 | 73 | 9 |
20 | 高氯酸钡 | 85 | 26 |
21 | 高氯酸锌 | 96 | 46 |
22 | 六氟磷酸铵 | 86 | 43 |
23 | 高氯酸钙 | 98 | 49 |
24 | 碘化钐 | 98 | 37 |
25 | 六氟磷酸钾 | 97 | 36 |
26 | 六氟磷酸锂 | 78 | 9 |
27 | 三氟甲磺酸锌 | 98 | 44 |
28 | 三氟甲磺酸铜 | 93 | 48 |
29 | 三氟甲磺酸钐 | 84 | 32 |
30 | 三氟甲磺酸镁 | 94 | 41 |
31 | 三氟甲磺酸铟 | 89 | 39 |
32 | 三氟甲磺酸镍 | 100 | 56 |
33 | 三氟甲磺酸铁 | 93 | 39 |
34 | 三氟甲磺酸锰 | 93 | 44 |
35 | 三氟甲磺酸锡 | 96 | 42 |
36 | 三氟甲磺酸铽 | 90 | 41 |
37 | 高氯酸镉 | 98 | 64 |
38 | 高氯酸铁 | 97 | 52 |
39 | 高氯酸锰 | 98 | 59 |
40 | 高氯酸铟 | 99 | 59 |
* 非本发明的对比实验。
实施例2)
为了证明所要求保护的胺的特别的反应性,首先将模型实验相互比较。为此各自将0.025摩尔(3.75g)1,2-环氧-3-苯氧基丙烷加入到22.68g甲苯(溶剂)和2.08g十四烷(内标)的混合物中。此外加入0.025NH当量的胺和0.06g三氟甲磺酸钙。在混合之后立即进行GC,并且将1,2-环氧-3-苯氧基丙烷的含量与十四烷的含量进行比较。在室温下4小时后,通过GC分析测定1,2-环氧-3-苯氧基丙烷(EP)的残余含量(通过内标十四烷校准)。在此产生以下结果:
胺 | 0样品中的% EP | 在室温下4小时后的% EP | 在5℃下4小时后的% EP | |
1* | 丁铵 | 92 | 52 | 73 |
2* | 甲基丙胺 | 92 | 46 | 91 |
3* | 乙醇胺 | 91 | 63 | 80 |
4 | 哌啶 | 93 | 0 | 32 |
* 非根据本发明的对比实验。
由该模型实验清楚地看出,所要求保护的组合物比常规体系具有显著更高的反应性。
对比例3a)
将100份氨基乙基哌嗪(AEP,Aldrich)与446份Epikote 828(环氧当量190,Hexion)紧密混合,然后立即制进行DSC。
对比例3b)
在100份氨基乙基哌嗪(AEP,Aldrich)中溶解0.5份三氟甲磺酸钙(Aldrich),并将该混合物与446份Epikote 828(环氧当量190,Hexion)紧密混合,然后立即进行DSC。
在根据本发明的实验中,放热峰低23℃且该放热峰的起始低29℃。因此,根据本发明的反应性组合物具有显著更高的反应性。
Claims (17)
1.组合物,其包含
a) 至少一种环氧树脂,
b) 至少一种式(I)的环状胺
其中
- R1至R4表示H或有机基团,且
- X = –(Y1)m-(A1)n-(Y2)o-(A2)p-(Y3)q-(A3)r-(Y4)s– (II)
其中彼此独立地
- m、n、o、p、q、r和s = 0或1,
- A1、A2、A3 = 亚烷基或亚烯基,且
- Y1、Y2、Y3、Y4 = NR5、PR5、O或S,其中R5彼此独立地= 有机基团,
- 其中选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的各两个有机基团也可以形成一个或多个其它环,
条件是,选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团中的至少一个存在的基团被至少一个基团–NHR6或–NH2取代,其中R6 = 有机基团,和
c) 至少一种极强布朗斯台德酸的盐,其具有选自金属离子、含金属的离子、鏻离子和未取代的铵离子的反荷离子。
2.根据权利要求1的组合物,
其特征在于,
所述环氧树脂的环氧基团与所有胺的所有NH基团的总和的比率为0.5 : 1至1.5 : 1。
3.根据权利要求1或2的组合物,
其特征在于,
所述至少一种环氧树脂是基于双酚A-二缩水甘油醚、双酚F-二缩水甘油醚、4,4'-亚甲基-双[N,N-双(2,3-环氧丙基)苯胺]、己二醇二缩水甘油醚、丁二醇二缩水甘油醚、三羟甲基丙烷三缩水甘油醚、1,2,3-丙三醇三缩水甘油醚、季戊四醇四缩水甘油醚和六氢邻苯二甲酸二缩水甘油酯的多环氧化物。
4.根据前述权利要求任一项的组合物,
其特征在于,
在式(I)中,基团R1、R2、R3和R4中的至少两个= H。
5.根据前述权利要求任一项的组合物,
其特征在于,
A1、A2和A3彼此独立地具有式(III)
-(CR7R8)x-(CR9=CR10)y-(CR11R12)z- (III)
其中彼此独立地
- R7、R8、R9、R10、R11和R12 = H或有机基团,且
- 1 ≤ x + y + z ≤ 7。
6.根据前述权利要求任一项的组合物,
其特征在于,
式(II)中的X具有2至15个原子的链长。
7.根据前述权利要求任一项的组合物,
其特征在于,
X具有式(IIa)
X = –(CR7R8)x-(Y)o-(CR11R12)z– (IIa)
其中
- x和z = 0、1、2、3、4、5、6或7,
- o = 0或1,
- 2 ≤ x + o + z ≤ 15
- R7、R8、R11、R12 = H或有机基团,且
- Y = NR5、PR5、O或S,其中R5 = 有机基团。
8.根据权利要求7的组合物,
其特征在于,
x = 1、2、3或4,o = 0或1且z = 0、1或2。
9.根据权利要求1 - 6任一项的组合物,
其特征在于,
式(I)的环状胺是一种三氮杂环己烷或三氮杂环庚烷。
10.根据前述权利要求任一项的组合物,
其特征在于,
所述至少一种式(I)的环状胺选自1-(2-氨基乙基)哌嗪、1-(3-氨基丙基)哌嗪、1-咪唑烷乙胺、咪唑烷-N-丙胺、α-甲基-1-哌嗪乙胺、2,6-二甲基-1-哌嗪乙胺、2-氨基-1-(哌嗪-1-基)乙酮、4-(2-氨基乙基)哌啶、3-(2-氨基乙基)哌啶和2-(2-氨基乙基))哌啶。
11.根据前述权利要求任一项的组合物
其特征在于,
所述极强酸的盐是碱土金属盐、锂盐、铝盐、铋盐、锌盐、铕盐、四苯基锑盐、鏻盐或未取代的铵盐。
12.根据前述权利要求任一项的组合物
其特征在于,其此外具有
d) 不包括在式(I)下的胺,和/或
e) 其它助剂或添加剂。
13.根据权利要求12的组合物,
其特征在于,
不包括在式(I)下的胺d)选自
- 脂族胺,
- 氧化烯多胺,
- 脂环族胺,
- 芳脂族胺,
- 芳族胺,
- 加成固化剂,
- 聚酰胺基胺固化剂
- 曼尼希碱固化剂,和
- 曼尼希碱。
14.根据权利要求12或13任一项的组合物
其特征在于,
所述组合物以下列重量百分比例具有组分a)至e),基于所述组合物的总质量计:
a) 环氧树脂30 – 95 %
b) 环状胺1 – 50 %
c) 极强布朗斯台德酸的盐0.001 – 5 %
d) 其它胺0 – 48 %,和
e) 其它助剂或添加剂0 – 48 %。
15.根据权利要求12 – 14的组合物,
其特征在于,
胺b)的重量百分比例为至少10重量%,基于胺b)和d)的总质量计。
16.制备根据前述权利要求1 – 15任一项的组合物的方法,
其特征在于,将至少一种环氧树脂a)、至少一种环状胺b)和至少一种极强布朗斯台德酸的盐c)相互混合。
17.根据权利要求1 -15任一项的组合物作为浇注树脂、涂料物料、复合材料或胶粘剂或作为它们的组成部分的用途。
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US11286335B2 (en) | 2022-03-29 |
EP3569632B1 (de) | 2023-12-06 |
KR20190132249A (ko) | 2019-11-27 |
US20190352450A1 (en) | 2019-11-21 |
EP3569632A1 (de) | 2019-11-20 |
JP2019199610A (ja) | 2019-11-21 |
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