CN111234182A - 快速固化的环氧体系 - Google Patents
快速固化的环氧体系 Download PDFInfo
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- CN111234182A CN111234182A CN201911190359.9A CN201911190359A CN111234182A CN 111234182 A CN111234182 A CN 111234182A CN 201911190359 A CN201911190359 A CN 201911190359A CN 111234182 A CN111234182 A CN 111234182A
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- amine
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- alcohol
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- 239000004593 Epoxy Substances 0.000 title abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 150000001412 amines Chemical class 0.000 claims abstract description 50
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 27
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 23
- 239000003822 epoxy resin Substances 0.000 claims abstract description 22
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 22
- 238000002360 preparation method Methods 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000005233 alkylalcohol group Chemical group 0.000 claims abstract description 6
- -1 2' -bipiperidine Chemical compound 0.000 claims description 26
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 24
- 150000003254 radicals Chemical class 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 229920000768 polyamine Polymers 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 7
- FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 239000007795 chemical reaction product Chemical class 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- JOMNTHCQHJPVAZ-UHFFFAOYSA-N 2-methylpiperazine Chemical compound CC1CNCCN1 JOMNTHCQHJPVAZ-UHFFFAOYSA-N 0.000 claims description 4
- BHHMPZQRVWVAAR-UHFFFAOYSA-N 7-bromo-8-methylpyrido[2,3-b]pyrazine Chemical compound C1=CN=C2C(C)=C(Br)C=NC2=N1 BHHMPZQRVWVAAR-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- 125000002015 acyclic group Chemical group 0.000 claims description 4
- 239000000853 adhesive Substances 0.000 claims description 4
- 230000001070 adhesive effect Effects 0.000 claims description 4
- 150000004982 aromatic amines Chemical class 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 claims description 3
- PLDLPVSQYMQDBL-UHFFFAOYSA-N 2-[[3-(oxiran-2-ylmethoxy)-2,2-bis(oxiran-2-ylmethoxymethyl)propoxy]methyl]oxirane Chemical compound C1OC1COCC(COCC1OC1)(COCC1OC1)COCC1CO1 PLDLPVSQYMQDBL-UHFFFAOYSA-N 0.000 claims description 3
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 claims description 3
- 238000005266 casting Methods 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 229920000962 poly(amidoamine) Polymers 0.000 claims description 3
- 229920005989 resin Polymers 0.000 claims description 3
- 239000011347 resin Substances 0.000 claims description 3
- GLUABPSZMHYCNO-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,2-b]pyrrole Chemical compound N1CCC2NCCC21 GLUABPSZMHYCNO-UHFFFAOYSA-N 0.000 claims description 2
- QFCMBRXRVQRSSF-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydropyrrolo[3,4-c]pyrrole Chemical compound C1NCC2CNCC21 QFCMBRXRVQRSSF-UHFFFAOYSA-N 0.000 claims description 2
- JPOVEXSHVNWPRM-UHFFFAOYSA-N 1,2,3,4,4a,5,5a,6,7,8,9,9a,10,10a-tetradecahydrophenazine Chemical compound N1C2CCCCC2NC2C1CCCC2 JPOVEXSHVNWPRM-UHFFFAOYSA-N 0.000 claims description 2
- SAJIWHKJMCWNFA-UHFFFAOYSA-N 1,2,3,4,4a,5,6,6a,7,8,9,10,10a,10b-tetradecahydro-4,7-phenanthroline Chemical compound C1CC2NCCCC2C2C1NCCC2 SAJIWHKJMCWNFA-UHFFFAOYSA-N 0.000 claims description 2
- RXYRNRQEFMJQOV-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydro-2,6-naphthyridine Chemical compound C1NCCC2CNCCC21 RXYRNRQEFMJQOV-UHFFFAOYSA-N 0.000 claims description 2
- XVBWSIVJQVABMM-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydro-2,7-naphthyridine Chemical compound C1CNCC2CNCCC21 XVBWSIVJQVABMM-UHFFFAOYSA-N 0.000 claims description 2
- MDEXMBGPIZUUBI-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoxaline Chemical compound N1CCNC2CCCCC21 MDEXMBGPIZUUBI-UHFFFAOYSA-N 0.000 claims description 2
- ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical compound C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 claims description 2
- DNXNNXUNSOIEQP-UHFFFAOYSA-N 1,4,8-triazaspiro[4.5]decane Chemical compound N1CCNC11CCNCC1 DNXNNXUNSOIEQP-UHFFFAOYSA-N 0.000 claims description 2
- AIIGJUUIWYQTJQ-UHFFFAOYSA-N 1,4-diazaspiro[4.5]decane Chemical compound N1CCNC11CCCCC1 AIIGJUUIWYQTJQ-UHFFFAOYSA-N 0.000 claims description 2
- XDHVNMPVLPEHND-UHFFFAOYSA-N 1-(2-piperazin-1-ylethyl)piperazine Chemical compound C1CNCCN1CCN1CCNCC1 XDHVNMPVLPEHND-UHFFFAOYSA-N 0.000 claims description 2
- JDEPFXMUEWMBRH-UHFFFAOYSA-N 1-piperidin-2-ylpiperazine Chemical compound N1CCCCC1N1CCNCC1 JDEPFXMUEWMBRH-UHFFFAOYSA-N 0.000 claims description 2
- UWQVPLPJLRBXRH-UHFFFAOYSA-N 2,3,3a,4,5,6,7,7a-octahydro-1h-pyrrolo[3,2-c]pyridine Chemical compound C1NCCC2NCCC21 UWQVPLPJLRBXRH-UHFFFAOYSA-N 0.000 claims description 2
- KSCPLKVBWDOSAI-UHFFFAOYSA-N 2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCCC2CNCC21 KSCPLKVBWDOSAI-UHFFFAOYSA-N 0.000 claims description 2
- ICGDKKACLISIAM-UHFFFAOYSA-N 2,3,5,6-tetramethylpiperazine Chemical compound CC1NC(C)C(C)NC1C ICGDKKACLISIAM-UHFFFAOYSA-N 0.000 claims description 2
- OMEMBAXECFIRSG-UHFFFAOYSA-N 2,3,5-trimethylpiperazine Chemical compound CC1CNC(C)C(C)N1 OMEMBAXECFIRSG-UHFFFAOYSA-N 0.000 claims description 2
- COWPTMLRSANSMQ-UHFFFAOYSA-N 2,3-dimethylpiperazine Chemical compound CC1NCCNC1C COWPTMLRSANSMQ-UHFFFAOYSA-N 0.000 claims description 2
- NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 claims description 2
- KCKUZYPQEGUWNK-UHFFFAOYSA-N 2-(piperidin-2-ylmethyl)piperidine Chemical compound C1CCCNC1CC1CCCCN1 KCKUZYPQEGUWNK-UHFFFAOYSA-N 0.000 claims description 2
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 claims description 2
- DXOHZOPKNFZZAD-UHFFFAOYSA-N 2-ethylpiperazine Chemical compound CCC1CNCCN1 DXOHZOPKNFZZAD-UHFFFAOYSA-N 0.000 claims description 2
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 claims description 2
- GXXKZNABQGUBCX-UHFFFAOYSA-N 2-piperazin-1-yl-n-(2-piperazin-1-ylethyl)ethanamine Chemical compound C1CNCCN1CCNCCN1CCNCC1 GXXKZNABQGUBCX-UHFFFAOYSA-N 0.000 claims description 2
- GBNSORAUUDWAQH-UHFFFAOYSA-N 2-piperidin-2-ylpiperazine Chemical compound N1C(CCCC1)C1NCCNC1 GBNSORAUUDWAQH-UHFFFAOYSA-N 0.000 claims description 2
- LKDJYZBKCVSODK-UHFFFAOYSA-N 3,8-diazabicyclo[3.2.1]octane Chemical compound C1NCC2CCC1N2 LKDJYZBKCVSODK-UHFFFAOYSA-N 0.000 claims description 2
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 claims description 2
- OXEZLYIDQPBCBB-UHFFFAOYSA-N 4-(3-piperidin-4-ylpropyl)piperidine Chemical compound C1CNCCC1CCCC1CCNCC1 OXEZLYIDQPBCBB-UHFFFAOYSA-N 0.000 claims description 2
- VMJOIXFVKVPLRQ-UHFFFAOYSA-N 6-methyl-1,4-diazepane Chemical compound CC1CNCCNC1 VMJOIXFVKVPLRQ-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
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 150000003938 benzyl alcohols 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
- 238000009835 boiling Methods 0.000 claims description 2
- 239000000470 constituent Substances 0.000 claims description 2
- HTFFABIIOAKIBH-UHFFFAOYSA-N diazinane Chemical compound C1CCNNC1 HTFFABIIOAKIBH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012971 dimethylpiperazine Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical group O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 2
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 18
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 11
- 150000002170 ethers Chemical class 0.000 description 11
- 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 9
- 150000001298 alcohols Chemical class 0.000 description 8
- 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 8
- 150000002989 phenols Chemical class 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- 125000000962 organic group Chemical group 0.000 description 7
- 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
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 229920005862 polyol Polymers 0.000 description 5
- 150000003077 polyols Chemical class 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 4
- 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 3
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 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
- YCUKMYFJDGKQFC-UHFFFAOYSA-N 2-(octan-3-yloxymethyl)oxirane Chemical compound CCCCCC(CC)OCC1CO1 YCUKMYFJDGKQFC-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
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- 239000007848 Bronsted acid Substances 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-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
- 238000006683 Mannich reaction Methods 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-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
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 150000001925 cycloalkenes Chemical class 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000007872 degassing Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 150000002462 imidazolines Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006224 matting agent Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- ITZPOSYADVYECJ-UHFFFAOYSA-N n'-cyclohexylpropane-1,3-diamine Chemical compound NCCCNC1CCCCC1 ITZPOSYADVYECJ-UHFFFAOYSA-N 0.000 description 2
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Abstract
本发明涉及快速固化的环氧体系。具体地,本发明涉及包含至少一种环氧树脂,至少一种具有至少两个均为有机环体系的组成部分的仲氨基的胺和至少一种任选被至少一个芳族基团和/或至少一个烯基基团取代的烷基醇的组合物、其制备方法及其用途。
Description
技术领域
本发明涉及快速固化的环氧体系。
背景技术
环氧树脂,特别是由双酚A和表氯醇制得的环氧树脂,是制备高品质的浇铸树脂,涂覆物料,复合材料和粘合剂的已知原料。用多胺固化的芳族环氧树脂不仅具有好的耐化学性和耐溶剂性,而且在许多基底上均具有好的粘合强度。
为了加快环氧-胺涂覆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公开了使用各种胺的环氧树脂的催化固化。
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公开了使用氨基乙基哌嗪的环氧树脂的无催化剂固化。
EP 0 969 030 A1公开了环氧/胺涂覆体系,其胺组分是脂族胺。该组合物可以包含催化剂。在实施例中还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各种胺的四氟硼酸盐或六氟磷酸盐的情况下尤其使用氨基乙基哌嗪,双(氨基丙基)哌嗪或哌啶的环氧树脂的固化。
EP 3 255 078 A1公开了环氧树脂组合物,其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-1,3-二胺和任选的催化剂,该催化剂尤其可以是无机盐。
已经发现,用具有至少两个均为有机环体系的组成部分的仲氨基的胺可以特别快速地固化环氧树脂组合物。
US 8,951,619 B2和US 9,006,385 B2尤其公开了尤其使用未取代的哌嗪的环氧树脂的无催化剂固化。
WO 2017/074810 A1公开了包含环氧树脂、聚醚胺和其他胺固化剂的组合物,其中该胺固化剂尤其可以是咪唑或咪唑啉。还使用了金属三氟甲磺酸盐催化剂。
迄今为止未公开的EP 18172950.0公开了一种贫烷基酚的组合物,其包含至少一种环氧树脂,至少一种具有至少两个均为有机环体系的组成部分的仲氨基的胺和至少一种强布朗斯台德酸的盐。迄今为止未公开的EP 18172954.2公开了一种贫烷基酚的组合物,其包含至少一种环氧树脂,至少一种具有至少两个均为有机环体系的组成部分的仲氨基的胺和至少一种非常强的布朗斯台德酸的盐。
US 2012/0010330 A1公开了在至少10%的烷基酚存在下尤其使用选自哌嗪或高哌嗪的环状二胺的环氧树脂的固化,以提高组合物的反应性并降低玻璃化转变温度Tg(烷基酚用作增塑剂)。然而,使用含酚添加物质的缺点是其致敏性作用和其毒性。
现有技术组合物的共同点在于,它们固化太慢或仅在高温下固化并且由此反应性不足。
然而,对于许多应用而言,重要的是表面固化或完全的充分固化要特别快速地进行或在低温下进行。首先,可以提高生产率或可以加快下一个处理步骤。其次,尤其在寒冷地区重要的是,为例如船舶或管道提供防腐蚀涂层,从而在那里在冬季也可以继续工作。
发明内容
因此,本发明所基于的目的在于提供环氧体系,其与迄今已知的配制剂相比在相同条件下反应快得多并且具有低玻璃化转变温度Tg。目的还在于提供环氧配制剂,其在远低于室温的温度下比迄今可能更快地部分或完全固化。还希望它们尽可能地不含毒性和致敏性的添加物。
本发明的目的通过根据本发明的组合物实现,该组合物包含
a)至少一种环氧树脂,
b)至少一种环状胺,其具有至少两个均为有机环体系的组成部分的仲氨基,和
c)至少一种任选被至少一个芳族基团和/或至少一个烯基基团取代的烷基醇。
优选地,基于所述组合物的总质量,所述组合物包含小于5重量%,进一步优选小于3重量%的取代或未取代的酚。进一步优选地,根据本发明的组合物还是不含酚的,即它们不包含酚或取代的酚。取代的酚在此应理解为是指结构上衍生自苯酚的化合物。特别地,根据本发明的组合物优选不包含烷基化的酚。相应的贫酚或不含酚的组合物具有低的毒性和致敏性的优点。
组分a)是至少一种环氧树脂。原则上所有环氧化合物均适用于该目的。
合适的环氧化合物描述在例如EP 675 185 A2中。可以考虑各种每分子含有多于一个环氧基团,优选两个环氧基团的已知化合物。这些环氧化合物在此既可以是饱和的也可以是不饱和的,以及可以是脂族的,脂环族的,芳族的或杂环的,并且还可以具有羟基。它们还可以包含在混合-或反应条件下不会引起干扰性的副反应的取代基,例如烷基-或芳基取代基或醚基团。
在此优选的环氧化合物是缩水甘油醚,其衍生自多元酚,尤其是双酚和酚醛树脂(Novolaken),并且其基于环氧基团ME的数量的摩尔质量(“环氧当量”,“EV-值”)为100至1500 克/当量,尤其是150至250 克/当量。
特别优选的环氧化合物衍生自间苯二酚、氢醌、2,2-双(4-羟苯基)-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-羟苯基)-1,1-乙烷、双(4-羟苯基)-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-羟苯基)-甲烷、双(4-羟苯基)-醚、双(4-羟苯基)-砜以及上述化合物的氯化和溴化产物(例如四溴双酚A)。
非常特别优选使用具有150至200 克/当量的环氧当量的基于双酚A和双酚F的液体二缩水甘油醚。
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(包括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、更高级聚氧基亚烷基二醇二缩水甘油醚,例如更高级聚氧基乙二醇二缩水甘油醚和聚氧基丙二醇二缩水甘油醚、共聚氧基乙二醇-丙二醇二缩水甘油醚、聚氧基丁二醇二缩水甘油醚、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或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、三缩水甘油基三(2-羟乙基)异氰脲酸酯。
还优选考虑作为组分A)的是:可通过表氯醇与胺如苯胺、正丁胺、双(4-氨基苯基)甲烷、间苯二甲胺或双(4-甲基氨基苯基)甲烷的反应产物的脱卤化氢而获得的多(N-缩水甘油基)化合物。然而,该多(N-缩水甘油基)化合物还可列举三缩水甘油基异氰脲酸酯、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,也可以使用通过表氯醇或类似的环氧化合物与脂族、脂环族或芳族多元羧酸如草酸、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如二聚或三聚亚麻酸的反应获得的多羧酸的多缩水甘油酯。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。
还优选的是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。除多缩水甘油醚之外,也可以同时使用基于多缩水甘油醚质量的质量含量至多30重量%,优选10至20重量%的少量单环氧化物,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、烷氧基化月桂醇的缩水甘油醚以及单环氧化物,如环氧化单不饱和烃(环氧丁烷、环氧环己烷、氧化苯乙烯)。
合适的环氧化合物的详细列举可以参照手册A. M. Paquin, "Epoxidverbindungen und Epoxidharze", Springer Verlag, Berlin 1958,第IV章和LeeNeville, "Handbook of Epoxy Resins", 1967, 第2章。
作为环氧化合物在此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。此类环氧化物的实例还有三缩水甘油基异氰脲酸酯(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)缩水甘油酯(商品名CARDURA E10, Shell),3,4-环氧环己基甲基3',4'-环氧环己烷甲酸酯(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)和其他具有游离环氧基的Polypox类型。
也可以使用所述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(Polyepoxide)。
优选使用前述环氧化合物的混合物作为组分A)。
作为具有至少两个均为有机环体系的组成部分的仲氨基的胺b),原则上可以考虑具有至少两个环仲氨基的所有化合物。此外,胺b)作为NH-载体,还可具有其他伯氨基或非环仲氨基。然而,优选地,根据本发明的组合物中使用的胺不具有其他伯氨基或非环仲氨基,即它们仅具有至少两个均为有机环体系的组成部分的仲氨基。然而,此外,根据本发明使用的胺还可以具有非反应性的叔氨基。
“有机环体系”应理解为是指可以具有一个、两个或至少三个(任选与非含氮杂环或非杂环稠合的)含氮杂环的杂环体系。所述有机环体系在此还可以在含氮环中具有除氮以外的其他杂原子,特别是氧、硫和/或磷。在本发明中,“含氮环”在此应理解为是指单环含氮环或与非含氮杂环,环烷烃,环烯烃或芳族烃共享环键(即任选与非含氮杂环,环烷烃,环烯烃或芳族烃稠合的含氮环)的单环含氮环。
具有至少两个仲氨基的胺也可以是具有环仲氨基和任选其他伯氨基或非环仲氨基的化合物与对NH-基团具有反应性的基团的相应反应产物,特别是单-和多环氧化物(加合物),多异氰酸酯,聚碳二亚胺,酚(醛和酮的曼尼希反应)和取代的酚(曼尼希碱的交换),聚酯,多元羧酸,聚丙烯酸酯和聚甲基丙烯酸酯。
在一个优选的实施方案中,胺b)是具有至少两个环仲氨基的胺,其中至少两个属于不同的环。特别优选地,胺b)是在两个至四个不同的环上具有两个至四个环仲氨基的胺。具有至少两个不同环的相应胺优选也应理解为是指由至少两个单环杂环组成的稠合杂环。
非常特别优选地,所述至少两个环仲氨基属于相同的环。
甚至更优选的胺b)具有式(I)
其中
- R1至R4为H或有机基团,并且
- 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,和
· Y1、Y2、Y3、Y4 = NR5、PR5、O或S,其中R5彼此独立地为H或有机基团,
· 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他环,
- 前提是存在的选自Y1、Y2、Y3、Y4的基团中的至少一个是NR5,其中R5 = H。
就式(I)所示的环而言,环状胺是饱和的或部分不饱和的。相应的胺比未落入该式的芳族胺和咪唑啉反应更快。任选存在于环状胺中的其他环不仅可以是饱和的或不饱和的,而且可以是芳族的。优选地,任选存在于环状体系中的其他环是非芳族的,即饱和的或不饱和的。
就式(I)所示的环而言,优选的环状胺是饱和的。
优选地,与环上氨基相邻的碳原子的至少一个为H,即基团R1、R2、R3和R4中的至少一个为H。进一步优选地,基团R1、R2、R3和R4中的至少两个为H。优选地,基团R1、R2、R3和R4中的至少三个,特别优选全部为H。相应未取代的胺比其他胺反应更快。
在基团X中,如果存在的话,A1、A2和A3彼此独立地为亚烷基或亚烯基。这些进而可以带有有机基团。如果所述亚烷基和/或亚烯基本身具有一个或多个有机基团,则选自该亚烷基和/或亚烯基的有机基团中的各两个有机基团还可以彼此或与任选存在的有机基团R1至R5形成一个或多个其他环。
选自R1至R5和任选存在的亚烷基和/或亚烯基A1、A2、A3的基团的存在基团可以被至少一个基团-NHR6或-NH2取代,其中R6为有机基团。这意味着,在式(I)中除所述至少两个环氨基之外,也还可以存在其他伯氨基或非环仲氨基。
优选地,如果存在,A1、A2和A3分别彼此独立地具有式(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,和
· 1 ≤ x + y + z ≤ 7。
系数x、y和z还可以根据它们与基团A1,A2和A3的相关性优选地标记为系数x1、y1和z1,x2、y2和z2以及x3、y3和z3。
优选地,X具有2至15个原子的链长。优选地,所有x、½·y和z以及m、o、q和s的总和因此为2至15的值,更优选2至8的值,甚至更优选2至5的值和非常特别优选2至4的值。也就是说,优选2 ≤ m + o + q + s + x1 + ½·y1 + z1 + x2 + ½·y2 + z2 + x3 + ½·y3 +z3 ≤ 15。进一步优选2 ≤ m + o + q + s + x1 + ½·y1 + z1 + x2 + ½·y2 + z2 + x3 +½·y3 + z3 ≤ 8,进一步优选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)环化合物,因为与氨基相邻的两个碳原子在两侧上与式(II)的取代的(杂)亚烷基键合。
进一步优选地,式(I)除了环上NH-基团的氮原子之外,在环中具有至多一个其他杂原子,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 = 1,
· 2 ≤ x + o + z ≤ 15,
· R7,R8,R11,R12 = H或有机基团,和
· Y= NH。
非常特别优选地,在式(IIa)中,x = z = 1。
相应地,则式(I)中选自R1至R8、R11和R12中的各两个有机基团也可以形成一个或多个其他环。
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。这些可以在它们的链内被杂原子取代和/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,其可在链内带有一个或多个醚基、羧基、氨基、酰胺基、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具有一个或多个选自羟基、腈基、卤素基团和有机基团的取代基,其中后者包括醚基、羧基、氨基、酰胺基、脲基、氨基甲酸酯基、碳酸酯基、脒基或胍基或本身可以被羟基、腈基或卤素基团取代。
特别优选的胺b)选自3,7-二氮杂双环[4.3.0]壬烷、2,8-二氮杂双环[4.3.0]壬烷、2-苯基-2-咪唑啉、3,8-二氮杂双环[3.2.1]辛烷、2,2'-双咪唑烷、1H-八氢-咪唑并[4,5-c]吡啶、1,4,8-三氮杂螺[4.5]癸烷、1,4-二氮杂螺[4.5]癸烷、吡唑烷、2,2-二甲基咪唑烷、1,4,7-三氮杂环壬烷、十氢-2,6-二甲基吡嗪并[2,3-b]吡嗪、六氢哒嗪、十氢-4a,8a-二甲基吡嗪并[2,3-b]吡嗪、4,4'-亚甲基双[哌啶]、2,2'-亚甲基双[哌啶]、十四氢-4,7-菲咯啉、2,2'-联哌啶、4,4'-联哌啶、十四氢吩嗪、十氢喹喔啉、1,5-十氢萘啶、八氢-1H-环戊吡嗪、2,2'-联吡咯烷、哌嗪、2-甲基哌嗪、2,2-二甲基哌嗪、2,3-二甲基哌嗪、2-乙基哌嗪、2,5-二甲基哌嗪、2,6-二甲基哌嗪、2,6-二氮杂双环[3.3.0]辛烷、3,7-二氮杂双环[3.3.0]辛烷、2,3,5,6-四甲基哌嗪、2,3,5-三甲基哌嗪、2,2'-联哌啶、2-(2-哌啶基)-哌嗪、2,2'-联吗啉、十氢-2,6-萘啶、十氢-2,7-萘啶、高哌嗪、2-甲基高哌嗪、6-甲基-1,4-二氮杂环庚烷、双[2-(哌嗪-1-基)乙基]胺、1,2-二哌嗪基乙烷、1,3-双(4-哌啶基)丙烷和N-(4-哌啶子基甲基)-4-哌啶甲胺。
非常特别优选地,胺b)是高哌嗪。
任选被至少一个芳族基团和/或至少一个烯基基团取代的烷基醇C)(在下文中称为“醇”)是具有至少一个烷基键合的OH基团的化合物。因此,醇C)具有带有至少一个OH基的烷基。所述烷基醇可以仅由烷基和一个或多个OH基团组成。替代地,所述烷基醇还可以具有被至少一个芳族基团和/或至少一个烯基基团取代的烷基。优选仅具有一个OH基团的醇,即一元醇,特别是选自甲醇、乙醇、丙醇、丁醇、苄醇、取代的苄醇以及苄醇与环氧乙烷或环氧丙烷的反应产物的那些。然而,有利地也可以使用多元醇,特别是选自乙二醇、丙二醇、聚乙二醇、聚丙二醇、聚酯多元醇、聚醚多元醇、聚碳酸酯多元醇、聚己内酯多元醇和聚丙烯酸酯多元醇的那些。
优选的醇在室温下为液体。特别优选的醇在1013 毫巴下的沸点为至少200℃。
非常特别优选地,所述醇是苄醇。
组分C的存在量优选使得该醇对OH基团的总浓度的贡献为至少1.3 Mol/l,优选至少1.4 Mol/l。进一步优选地,该醇对OH基团的总浓度的贡献为至少1.5 Mol/l和非常特别优选至少1.6 Mol/l和甚至进一步优选至少1.8 Mol/l。相应的浓度在此可以从相应的起始重量得出。
优选地,所述醇(特别是苄醇)的比例为整个配制剂的至少20重量%,特别优选至少30重量%和非常特别优选至少40重量%。
优选地,根据本发明的组合物还可包含d)不具有至少两个作为有机环体系的组成部分的仲氨基的胺,和/或e)其他助剂或添加物质。
这种胺d)优选为二胺或多胺。这些可以是单体、低聚和/或聚合的化合物。优选的单体和低聚化合物选自二胺,三胺和四胺。二胺或多胺d)的氨基可以与伯、仲或叔碳原子键合,优选与伯或仲碳原子键合。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),优选单独或混合使用以下胺:
• 脂族胺,尤其是聚亚烷基多胺,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,优选选自聚氧化丙烯二胺和聚氧化丙烯三胺(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,优选选自异佛尔酮二胺(3,5,5-三甲基-3-氨基甲基环己基胺)、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(单独或以异构体混合物形式)、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,
• 具有环氨基和至少一个非环伯或仲氨基的胺,优选1-(3-氨基乙基)哌嗪(AEP),1-(3-氨基丙基)哌嗪;
• 芳脂族胺,优选苯二甲胺;
• 芳族胺,优选苯二胺,尤其是1,3-苯二胺和1,4-苯二胺,和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、任选单独或以异构体混合物形式;
• 加合物固化剂,特别是环氧化合物,尤其是双酚A和F的缩水甘油醚与过量胺的反应产物;
• 聚酰氨基胺固化剂,特别是通过一元羧酸和多元羧酸与多胺的缩合,非常特别是通过二聚脂肪酸与多亚烷基多胺(Polyalkylenpolyaminen)的缩合而获得的聚酰氨基胺固化剂;
• 曼尼希碱固化剂,特别是通过一元-或多元酚与醛(尤其是甲醛)和多胺反应而获得的曼尼希碱固化剂;和
• 曼尼希碱,尤其是基于苯酚和/或间苯二酚,甲醛和间苯二甲胺,以及N-氨基乙基哌嗪和N-氨基乙基哌嗪与壬基苯酚和/或苄醇的混合物,由腰果酚、醛和胺在曼尼希反应中获得的酚醛胺(Phenalkamine)。
也可以使用前述二胺或多胺的混合物作为组分d)。
优选的其他助剂和添加物质e)可以是环氧化学中常规的化合物。优选的助剂和添加物质e)是颜料、溶剂、流平剂、改性剂、脱气剂、消光剂、反应性稀释剂和催化剂,例如水杨酸。
在一个优选的实施方案中,不使用胺d)。在一个优选的实施方案中,不包含其他改性剂。在一个优选的实施方案中,不使用催化剂。非常特别优选地,可能的助剂和添加物质因此限于颜料、溶剂、流平剂、脱气剂、消光剂和反应性稀释剂。
基于所述组合物的总质量,在根据本发明的组合物中的组分a)至e)的组成优选为以下重量百分比含量:
a)环氧树脂30-89%,
b)环状胺1-50%,
c)醇10-40%,
d)其他胺0-59%,以及
e)其他助剂或添加物质0-59%。
还优选地,基于胺b)和d)的总质量,胺b)的重量百分比含量为至少10重量%,特别优选至少30%,非常特别优选至少50%和更优选至少70%。
本发明的主题还在于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)和至少一种醇c)彼此混合。
本发明的主题还在于根据本发明的组合物作为浇铸树脂、涂覆物料、复合材料或粘合剂或其成分的用途。
具体实施方式
实验部分:
实施例1
将100份高哌嗪(Aldrich)与66份苄醇和380份Epikote 828(环氧当量190,Hexion)充分混合,然后立即进行DSC。
实施例2
将100份高哌嗪(Aldrich)与400份苄醇和380份Epikote 828(环氧当量190,Hexion)充分混合,然后立即进行DSC。
在实施例2中,放热峰较低,该放热峰的起始也是如此。因此,根据实施例2的组合物比根据实施例1的组合物更具反应性。
Claims (16)
1.组合物,其包含
a)至少一种环氧树脂,
b)至少一种胺,其具有至少两个均为有机环体系的组成部分的仲氨基,和
c)至少一种任选被至少一个芳族基团和/或至少一个烯基基团取代的烷基醇。
2.根据权利要求1所述的组合物,
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。
3.根据权利要求1或2所述的组合物,
其特征在于,
所有的环仲氨基均属于相同的环。
4.根据权利要求3所述的组合物,
其特征在于,
所述胺具有式(I)
其中
- R1至R4为H或有机基团,并且
- 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,和
· Y1、Y2、Y3、Y4 = NR5、PR5、O或S,其中R5彼此独立地为H或有机基团,
· 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他环,
- 前提是存在的选自Y1、Y2、Y3、Y4的基团中的至少一个是NR5,其中R5 = H。
5.根据前述权利要求中任一项所述的组合物,
其特征在于,
胺b)选自3,7-二氮杂双环[4.3.0]壬烷、2,8-二氮杂双环[4.3.0]壬烷、2-苯基-2-咪唑啉、3,8-二氮杂双环[3.2.1]辛烷、2,2'-双咪唑烷、1H-八氢-咪唑并[4,5-c]吡啶、1,4,8-三氮杂螺[4.5]癸烷、1,4-二氮杂螺[4.5]癸烷、吡唑烷、2,2-二甲基咪唑烷、1,4,7-三氮杂环壬烷、十氢-2,6-二甲基吡嗪并[2,3-b]吡嗪、六氢哒嗪、十氢-4a,8a-二甲基吡嗪并[2,3-b]吡嗪、4,4'-亚甲基双[哌啶]、2,2'-亚甲基双[哌啶]、十四氢-4,7-菲咯啉、2,2'-联哌啶、4,4'-联哌啶、十四氢吩嗪、十氢喹喔啉、1,5-十氢萘啶、八氢-1H-环戊吡嗪、2,2'-联吡咯烷、哌嗪、2-甲基哌嗪、2,2-二甲基哌嗪、2,3-二甲基哌嗪、2-乙基哌嗪、2,5-二甲基哌嗪、2,6-二甲基哌嗪、2,6-二氮杂双环[3.3.0]辛烷、3,7-二氮杂双环[3.3.0]辛烷、2,3,5,6-四甲基哌嗪、2,3,5-三甲基哌嗪、2,2'-联哌啶、2-(2-哌啶基)-哌嗪、2,2'-联吗啉、十氢-2,6-萘啶、十氢-2,7-萘啶、高哌嗪、2-甲基高哌嗪、6-甲基-1,4-二氮杂环庚烷、双[2-(哌嗪-1-基)乙基]胺、1,2-二哌嗪基乙烷、1,3-双(4-哌啶基)丙烷和N-(4-哌啶子基甲基)-4-哌啶甲胺。
6.根据前述权利要求中任一项所述的组合物,
其特征在于,
所述至少一种醇仅具有一个OH基团。
7.根据权利要求6所述的组合物,
其特征在于,
所述醇选自甲醇、乙醇、丙醇、丁醇、苄醇、取代的苄醇以及苄醇与环氧乙烷或环氧丙烷的反应产物。
8.根据前述权利要求中任一项所述的组合物,
其特征在于,
所述醇的沸点在1013毫巴下为至少200℃。
9.根据前述权利要求中任一项所述的组合物,
其特征在于,
所述醇是苄醇。
10.根据前述权利要求中任一项所述的组合物,
其特征在于,
所述醇对OH基团总浓度的贡献为至少1.3 Mol/l。
11.根据前述权利要求中任一项所述的组合物,
其特征在于,该组合物还包含
d)不具有至少两个作为有机环体系的组成部分的仲氨基的胺,和/或
e)其他助剂或添加物质。
12.根据权利要求11所述的组合物,
其特征在于,
所述胺d)选自
- 脂族胺,
- 氧化烯多胺,
- 脂环族胺,
- 具有环氨基和至少一个非环伯氨基或仲氨基的胺,
- 芳脂族胺,
- 芳族胺,
- 加合物固化剂,
- 聚酰氨基胺固化剂,
- 曼尼希碱固化剂,和
- 曼尼希碱。
13.根据前述权利要求中任一项所述的组合物,
其特征在于,
基于所述组合物的总质量,所述组合物包含以下重量百分比含量的组分a)至e):
a)环氧树脂30-89%
b)环状胺1-50%
c)醇10-40%
d)其他胺0-59%,以及
e)其他助剂或添加物质0-59%。
14.根据权利要求11至13中任一项所述的组合物,
其特征在于,
基于胺b)和d)的总质量计,胺b)的重量百分比含量为至少10重量%。
15.制备根据权利要求1至14中任一项所述的组合物的方法,
其特征在于,
将至少一种环氧树脂a)、至少一种环状胺b)和至少一种醇c)彼此混合。
16.根据权利要求1至14中任一项所述的组合物作为浇铸树脂、涂覆物料、复合材料或粘合剂或其成分的用途。
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US11286335B2 (en) | 2018-05-17 | 2022-03-29 | Evonik Operations Gmbh | Fast-curing epoxy systems |
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