TWI752973B - 作為快速環氧固化劑之室溫離子液體 - Google Patents
作為快速環氧固化劑之室溫離子液體 Download PDFInfo
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- TWI752973B TWI752973B TW106121137A TW106121137A TWI752973B TW I752973 B TWI752973 B TW I752973B TW 106121137 A TW106121137 A TW 106121137A TW 106121137 A TW106121137 A TW 106121137A TW I752973 B TWI752973 B TW I752973B
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- Prior art keywords
- epoxy
- amine
- curing agent
- group
- room temperature
- Prior art date
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- 239000004593 Epoxy Substances 0.000 title claims abstract description 99
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 67
- 239000011829 room temperature ionic liquid solvent Substances 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 124
- 150000003839 salts Chemical class 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 150000007524 organic acids Chemical class 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims description 65
- 229920000647 polyepoxide Polymers 0.000 claims description 48
- 239000003822 epoxy resin Substances 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 37
- 239000000047 product Substances 0.000 claims description 37
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 34
- -1 ether amine Chemical class 0.000 claims description 32
- 229920000768 polyamine Polymers 0.000 claims description 28
- 229920001281 polyalkylene Polymers 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 238000000576 coating method Methods 0.000 claims description 24
- 239000002131 composite material Substances 0.000 claims description 21
- 239000000853 adhesive Substances 0.000 claims description 16
- 230000001070 adhesive effect Effects 0.000 claims description 16
- 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 12
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 12
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 239000000565 sealant Substances 0.000 claims description 10
- 238000009408 flooring Methods 0.000 claims description 9
- 239000003607 modifier Substances 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 7
- 150000003141 primary amines Chemical class 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 7
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 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 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 125000004386 diacrylate group Chemical group 0.000 claims description 5
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 4
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 4
- CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 3
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 claims description 3
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 229920002635 polyurethane Polymers 0.000 claims description 2
- 239000004814 polyurethane Substances 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 2
- LKFAPHHHWRMPGC-UHFFFAOYSA-N butan-1-ol prop-2-enoic acid Chemical compound CCCCO.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C LKFAPHHHWRMPGC-UHFFFAOYSA-N 0.000 claims 1
- 239000007788 liquid Substances 0.000 abstract description 35
- 239000002253 acid Substances 0.000 abstract description 11
- 238000010494 dissociation reaction Methods 0.000 abstract description 3
- 230000005593 dissociations Effects 0.000 abstract description 3
- 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 26
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 24
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 20
- 239000000463 material Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 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 13
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 12
- 150000004982 aromatic amines Chemical class 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 150000002989 phenols Chemical class 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229960004889 salicylic acid Drugs 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 125000003700 epoxy group Chemical group 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000004567 concrete Substances 0.000 description 7
- 150000004665 fatty acids Chemical class 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 6
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- 239000004848 polyfunctional curative Substances 0.000 description 6
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- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 5
- 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 5
- 239000000654 additive Substances 0.000 description 5
- 229940106691 bisphenol a Drugs 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 238000001802 infusion Methods 0.000 description 5
- 239000002608 ionic liquid Substances 0.000 description 5
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
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- 125000003277 amino group Chemical group 0.000 description 4
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 CCC*C(C1C(CC2C(CC3)C3C2)CCC1)=C(C)C Chemical compound CCC*C(C1C(CC2C(CC3)C3C2)CCC1)=C(C)C 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical class O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
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- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
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- 239000007921 spray Substances 0.000 description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 3
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 description 2
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- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
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- 239000002841 Lewis acid Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 2
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- ZMBQZWCDYKGVLW-UHFFFAOYSA-N 1-methylcyclohexa-3,5-diene-1,2-diamine Chemical class CC1(N)C=CC=CC1N ZMBQZWCDYKGVLW-UHFFFAOYSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Natural products OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-UHFFFAOYSA-N 0.000 description 1
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- 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 1
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- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 1
- SFDRINJYDQTXRF-UHFFFAOYSA-N 2-[bis(dimethylamino)methyl]phenol Chemical compound CN(C)C(N(C)C)C1=CC=CC=C1O SFDRINJYDQTXRF-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- LSTZTHCEEPHCNQ-UHFFFAOYSA-N 3-(2,5-dioxabicyclo[2.1.0]pentan-3-yloxy)-2,5-dioxabicyclo[2.1.0]pentane Chemical compound C1(C2C(O2)O1)OC1C2C(O2)O1 LSTZTHCEEPHCNQ-UHFFFAOYSA-N 0.000 description 1
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 1
- DLYLVPHSKJVGLG-UHFFFAOYSA-N 4-(cyclohexylmethyl)cyclohexane-1,1-diamine Chemical compound C1CC(N)(N)CCC1CC1CCCCC1 DLYLVPHSKJVGLG-UHFFFAOYSA-N 0.000 description 1
- NOGYFAIHVRCHRE-UHFFFAOYSA-N 4-[(3,5-difluoro-4-hydroxyphenyl)methyl]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1CC1=CC(F)=C(O)C(F)=C1 NOGYFAIHVRCHRE-UHFFFAOYSA-N 0.000 description 1
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Abstract
本發明揭示之環氧固化劑具有包含至少一種室溫離子液體鹽之環氧固化劑，該室溫離子液體鹽為下列之反應產物：(a)至少一種以式(I)表示之聚伸烷基多胺(polyalkylene polyamine)化合物：
其中，x、y、及z為2或3之整數，m及n為1至3之整數；與(b)具有pKa(酸解離常數之對數的負數)低於6之有機酸。該液體鹽在大於15℃之溫度為安定液體。亦揭示包含該固化劑之可固化環氧系組成物以及由該可固化環氧系組成物所形成的物件。
Description
本發明係關於胺環氧固化劑之室溫離子液體以及關於含有此等液體鹽化合物之可固化環氧化物系組成物、以及亦關於製造此等化合物及組成物之方法。
環氧樹脂(epoxies)因其優異黏著性、耐化學性及耐熱性、良好至優異之機械性質、以及良好電絕緣性質而為人所知。固化環氧樹脂系統已發現在黏著劑、複合材料、塗料、建築產品、及地板產品之範圍的廣泛應用。特殊實例包括用於汽車、電子設備、航太及一般產業之雙組分環氧黏著劑、使用碳纖維及玻璃纖維強化物之環氧複合材料、用於金屬表面之保護性塗料、以及用於混凝土、膠結性或陶瓷基板之建築產品(經常稱為土木工程應用，諸如混凝土地板之調配物)。
固化環氧樹脂系統係由可彼此化學反應而形
成是為堅硬之熱固性材料的固化環氧樹脂之兩種組分組成。第一組分為環氧樹脂而第二組分為固化劑，經常稱為硬化劑。環氧樹脂為含有環氧基之物質或混合物。固化劑包括對環氧樹脂之環氧基具有反應性的化合物，諸如胺、羧酸、及硫醇(H.Lee及K.Neville "Handbook of Epoxy Resins" McGraw Hill,New York,1967，第5-1至5-24頁)。環氧樹脂可藉由固化劑交聯或固化。該固化程序為環氧樹脂中之環氧基與固化劑中之反應性基團的化學反應。該固化係藉由固化劑化學加成至環氧樹脂而將具有相對低分子量之環氧樹脂轉化成相對高分子量之材料。此外，該固化劑可促成固化環氧樹脂的許多性質。
在周圍溫度下之快速固化及/或冷固化環氧系統在許多應用中非常有用，如黏著劑、複合材料、電子設備、地板及塗料(亦包括水性組成物)。經當在周圍溫度下固化時，經改質之胺(如曼尼希鹼(Mannich base))、胺加成物及藉由三級胺(及其鹽)加速之胺、(烷基)酚或路易斯酸(Lewis acid)常用於此等應用。已知之其他環氧系統為經加速之聚硫醇，且被視為快速室溫固化環氧劑。
經加速之聚硫醇(如藉由Ancamine® K54固化劑加速之CAPCURE® 3-800)遭遇經加速之聚硫醇侷限於一些特殊應用的缺點，其中胺化學物質因其強烈氣味、不良耐熱水性及不良物理性質而無法符合固化速度要求。同樣的，藉由(烷基)酚加速之曼尼希鹼及固化劑遭遇彼等因游離(烷基)酚而造成環境、健康及安全性(EHS)問題的缺
點。胺、藉由三級胺加速之胺加成物以及曼尼希鹼顯示快速固化速度，然而，在沒有將會大幅降低該系統的耐熱性之特定添加量塑化劑協助的情況下，其將造成早期玻化並留下特定期間之易碎階段。酸係用以改善胺與環氧基之反應性的胺硬化劑之有效率加速劑種類，然而大部分有機酸及其胺鹽在無溶劑情況下為固體形式。因此，酸之添加係侷限於低水準以避免從該混合物分離出固體。一些強路易斯酸(例如BF3)可快速反應，但所得之固化環氧樹脂具有少許強度且實際上無用。
國際公開案WO2009080209A揭示與鹽化多胺或鹽化多胺-環氧加成物摻合以形成環氧樹脂之固化劑的酚烷基胺(phenalkamine)，其中，至少1/3之一級胺基係藉由與環氧基反應而被阻擋，並藉由添加酸性氫供體(柳酸(SA)或雙酚A(BPA))而「鹽化」。然而，沒有敘述關於該揭示方法中所使用的酸濃度或溶劑之細節。
國際公開案WO2013081895A揭示呈液體形式之胺/柳酸鹽，然而形成該鹽之2-甲基戊二胺(MPMD)中的所有胺基均為一級，且其中未揭示二級胺。在WO2013081895A中，亦提及一些胺與柳酸(SA)形成液體鹽，如Jeffamine D230、Jeffamine D400、三甲基五亞甲基二胺(TMD)及1,3二胺基甲基環己烷(1,3 BAC)。所有此等胺亦只含有一級胺基，且需要添加低含量SA以避免不可溶材料。
國際公開案WO2014028158A揭示硬化劑組成
物，其中，加速劑係藉由柳酸部分中和以置換曼尼希鹼。雖然WO2014028158A之中和方法併入第一改質劑(高沸點溶劑)及第一胺，但環脂族胺均均只含有一級胺基。
國際公開案WO2015144391揭示製造複合材料之方法(高壓RTM/HP-RTM)。關於硬化劑部分，將加速劑對甲苯磺酸(P-TSA)溶解於呈液體形式之1,3 BAC，然而當P-TSA添加量高(>10wt%)時需要水以防止沉澱。WO2015144391之胺1,3 BAC只含有一級胺基。
包括專利及專利申請案之前述公開案的揭示係以引用方式併入本文中。
如前文所述，環氧樹脂係經交聯或固化以發展特定特性。然而，許多應用遭遇在周圍溫度或低溫下固化緩慢或固化不足，及/或遭遇固化物件的品質方面之缺點。該產業需要發展在周圍溫度及低溫下快速固化且不遭遇已知固化劑的缺點之胺-環氧組成物。且更重要的是，室溫離子液體係呈液體形式，其將有利於摻合製程及貯存。
本揭示包括快速固化及/或冷固化環氧系統環氧固化劑。該環氧固化劑包括室溫離子液體(RTIL)作為胺環氧固化劑之建構組元或加速劑，以及關於含有此等液體鹽化合物之可固化環氧化物系組成物、以及亦關於製造此等化合物及組成物之方法。
在範例實施態樣中，本揭示包括具有至少一種室溫離子液體鹽之環氧固化劑。該室溫離子液體鹽為下列之反應產物：(a)至少一種以式(I)表示之聚伸烷基多胺化合物：
其中，x、y、及z為2或3之整數，m及n為1至3之整數；與(b)具有pKa(酸解離常數之對數的負數)低於6之有機酸。
本發明之鹽包含在大於15℃之溫度為安定液體的液體鹽，其在大於15℃及至高達約150℃之溫度下為安定的；在一些實例中在大於15℃至約200℃下為安定的。「液體」意指該鹽在約25℃之溫度下具有的黏度為約1000cps至約300,000cps。「安定」意指該液體鹽可在大於約15℃之溫度下貯存安定(維持液態)超過1個月。本發明之鹽可具有之胺值為約200mgKOH/g至約1600mgKOH/g，及在一些實例中為約400mgKOH/g至約900mgKOH/g。
在另一範例實施態樣中，本揭示包括環氧組成物。該環氧組成物包括可固化環氧系組成物，其包含(i)至少一種環氧樹脂，以及(ii)具有至少一種室溫離子液體鹽之環氧固化劑。該室溫離子液體鹽為下列之反應產物：
(a)至少一種以式(I)表示之聚伸烷基多胺化合物：
其中，x、y、及z為2或3之整數，m及n為1至3之整數；與具有pKa低於6之有機酸。該液體鹽在大於15℃之溫度為安定液體。
在另一範例實施態樣中，本揭示包括形成固化環氧樹脂之方法。該形成固化環氧樹脂之方法包括混合根據本揭示之可固化環氧系組成物。
在另一範例實施態樣中，本揭示包括包含根據本揭示之可固化環氧系組成物的接觸產物之固化環氧樹脂。
在另一範例實施態樣中，本揭示包括自根據本揭示之可固化環氧系組成物的接觸產物形成之物件。
本發明之各種實施態樣可單獨使用或彼此組合使用。
本發明之其他特徵及優點將從下文較佳實施態樣之更詳細敘述並結合展現例如本發明之原理的附圖而明暸。
圖1為顯示根據本揭示之實例的等溫固化曲線
之圖形表示。
所提供者為作為環氧固化劑之室溫離子液體以及含有此等液體鹽化合物之環氧固化組成物，以及製造此等化合物及組成物之方法。根據本揭示之室溫離子液體環氧固化劑具有成本效益、提供尤其在周圍溫度及低溫下對於環氧樹脂之快速固化、以及適於作為單一快速固化劑或與另一胺環氧固化劑之共固化劑。適用之應用包括但不侷限於黏著劑、電子設備、複合材料、塗料、底漆、密封劑、固化混料、建築產品、地板產品及複合產品。另外，此等黏著劑、塗料、底漆、密封劑、或固化混料可施加至金屬、FRP複合材料、塑膠或膠結性基板。根據本揭示之環氧硬化劑包括一些顯著優點，如在室溫及低溫下與環氧基之高反應性、作為液體容易使用、減少或消除白化(blushing)、低氣味及高玻璃轉化溫度(Tg)。室溫離子液體鹽之另一關鍵益處係其不會引發環氧樹脂之大幅同元聚合作用，以及可促成非常良好之機械性質。
本揭示之實施態樣包括環氧固化劑。該環氧固化劑包括至少一種室溫離子液體鹽，該室溫離子液體鹽為下列之反應產物；(a)至少一種以式(I)表示之聚伸烷基多胺化合物：
其中，x、y、及z為2或3之整數，m及n為1至3之整數；與(b)具有pKa低於6之有機酸，其中該液體鹽在大於15℃之溫度為安定液體。
根據本揭示之上述聚伸烷基多胺化合物和有機酸的反應產物為室溫離子液體且在室溫下為液態。如本文中所使用之「室溫離子液體」(RTIL)鹽包括其中離子係不良配位的鹽，其造成在溫度下呈液體形式之該等化合物，在大於約15℃之溫度下(包括在室溫下)為安定液體。
在特定實施態樣中，該至少一種聚伸烷基多胺化合物為不同的聚伸烷基多胺化合物之混合物。適用之不同的聚伸烷基多胺化合物之實例包括但不侷限於N,N'-雙(3-胺基丙基)乙二胺(Am4)與N,N,N'-參(3-胺基丙基)乙二胺(Am5)之組合或Am4與三伸乙四胺(TETA)之組合或Am4與四伸乙五胺(TEPA)之組合。
在特定實施態樣中，該至少一種聚伸烷基多胺化合物為根據式(I)之聚伸烷基多胺的衍生物。適用之衍生物包括但不侷限於烷基化聚伸烷基多胺、苯甲基化聚伸烷基多胺、羥烷基化聚伸烷基多胺、及式(I)之聚伸烷基多胺加成物。
熟習本領域之人士將認可含有4或更多個氮原子之聚伸烷基多胺通常可作為複雜混合物取得。在該等複雜混合物中，通常看到該混合物中之大部分化合物具有相同氮原子數目。在該等反應混合物中，該等混合物中之副產物經常稱為同類物(congener)。例如，三伸乙四胺(TETA)之複雜混合物不只含有線型TETA，亦含有參-胺基乙基胺、N,N'-雙-胺基乙基哌
、及2-胺基乙基胺基乙基哌
。
與本發明配合使用之有機酸包括具有酸解離常數之對數的負數小於6(Pka<6)的任何有機酸。適用之有機酸包括但不侷限於對甲苯磺酸(p-TSA)(Pka~-1.34)、三氟甲磺酸(CF3SO3H)(Pka~-14)、氟代硫酸(FSO3H)(Pka~-15.1)、柳酸(Pka~2.97)、三氟乙酸(TFA)(Pka~-0.25)、2-乙基己酸(EHA)(Pka~4.82)、四氟硼酸(HBF4)(Pka~-4.9)、硫氰酸(HSCN)(Pka~-4)、及其組合。
在本揭示之特定實施態樣中，在形成反應產物之反應混合物中之組分(b)對組分(a)之莫耳比為大於0至1.8。在特別安定之實施態樣中，在形成該反應的反應混合物中之組分(b)對組分(a)的莫耳比為0.3至1.3。
根據本揭示，形成室溫離子液體鹽的反應包括使至少一種聚伸烷基多胺化合物與具有pKa小於6之有機酸接觸。該至少一種聚伸烷基多胺化合物與具有pKa小於6之有機酸的反應可在約50℃至約150℃、約60℃至約120℃、或約65℃至約110℃之反應溫度下進行1至10小時
或2至8小時或3至7小時。水及溶劑係在高度真空下於110℃自該組成物移除。
通常，該固化劑組成物具有基於100%固體計之胺氫當量(AHEW)為約15至約500。此外，該固化劑組成物可具有基於100%固體計之AHEW為約20至約300，或為約30至約200，或為約40至約150。
另外，本文所述之固化劑組成物可基於溶劑。或者，在本揭示之另一態樣中，此等組成物可進一步包含至少一種稀釋劑，諸如例如，有機溶劑、或有機或無機酸。適當之有機溶劑為熟習胺調配物化學領域之人士所熟知。適用於本揭示之範例有機溶劑包括但不侷限於苯甲醇、丁醇、甲苯、二甲苯、甲基乙基酮等、或其組合。有機及無機酸之非限制性實例為乙酸、胺磺酸、乳酸、柳酸、癸二酸、硼酸、磷酸等、或其組合。此等酸可提高該固化劑組成物之固化速度。
該固化劑組成物亦可進一步經單官能基環氧化物改質，該等單官能基環氧化物係諸如例如苯基環氧丙基醚、鄰甲苯酚基環氧丙基醚、對第三丁基苯基環氧丙基醚、正丁基環氧丙基醚、及其他相似之環氧丙基醚或酯。此外，本文所揭示之固化劑組成物可與其他市售固化劑摻合。此等市售固化劑包括但不侷限於基於溶劑、無溶劑或基於水之固化劑，其可針對諸如下列特定性質為目標而以摻合物形式使用：固化速率、乾燥速度、硬度發展、澄清度、及光澤。
在本揭示另一實施態樣中，可固化環氧系組成物含有(i)環氧樹脂、(ii)高於室溫之液體鹽化合物、(iii)隨意的第二胺、(iv)隨意的改質劑、及(v)隨意的丙烯酸酯(v)。例如，根據本揭示，該可固化環氧系組成物包括可固化環氧系組成物，該可固化環氧系組成物包括(i)至少一種環氧樹脂、及(ii)包含至少一種室溫離子液體鹽之環氧固化劑，該室溫離子液體鹽下列之反應產物：(a)至少一種以式(I)表示之聚伸烷基多胺化合物：
其中，x、y、及z為2或3之整數，m及n為1至3之整數；與(b)具有pKa低於6之有機酸，且該液體鹽在大於15℃之溫度為安定液體。隨意的，視所希望性質而定，各種添加劑可存在於所使用之組成物或調配物中以產生人造物件。此等添加劑可包括但不侷限於溶劑(包括水)、加速劑、塑化劑、填料、纖維(諸如玻璃纖維或碳纖維)、顏料、顏料分散劑、流變性改質劑、搖變減黏膠。
用於該可固化環氧系組成物之環氧樹脂(i)包括含有環氧基之物質或混合物。適用之環氧樹脂實例包括但不侷限於雙酚-A二環氧丙基醚(DGEBA)、雙酚-F二環氧丙基醚(BFDGE)、及環氧酚醛清漆。該環氧樹脂可隨意地藉由如下列之反應性稀釋劑稀釋：C12/C14環氧丙基醚、
丁二醇二環氧丙基醚、己二醇-二環氧丙基醚。
根據本揭示，固化劑組成物除了室溫離子液體鹽之外可進一步包含至少一種(iii)第二胺。第二胺包括至少一個氮原子，及可為一級胺、二級胺、三級胺、四級胺或其衍生物。第二胺之一實例包括多官能基胺。如本文所使用之多官能基胺描述具有胺官能度且含有三(3)或更多個活性胺氫之化合物。
在本揭示之特定實施態樣中，(iii)第二胺包括在該可固化環氧系組成物中或在該固化劑中。第二胺之實例包括但不侷限於聚伸烷基多胺、環脂族胺、芳族胺、聚(環氧烷)二胺或三胺、曼尼希鹼衍生物、聚醯胺衍生物及其組合。其他適用之第二胺包括但不侷限二乙醇胺、嗎啉、及PC-23作為二級胺、參-二甲胺基甲基酚(市售者為Air Products and Chemicals,Inc.之ANCAMINE® K-54)、DBU、TEDA作為三級胺。此外，該可固化環氧系組成物或固化劑可包括此等胺或胺衍生物之組合。該第二胺提供是為共固化劑、增韌劑、稀釋劑及/或加速劑之性質。適用之第二胺包括但不侷限於胺基乙基哌
、異佛酮二胺(IPDA)、4,4'-亞甲基雙(環己胺)PACM、氫化偏伸茬基二胺(商業上稱為1,3-BAC)、3,3'-二甲基-4,4'-二胺基二環己基甲烷(DMDC)、聚醚胺、及其組合。(iii)第二胺在該環氧固化劑中之組成範圍可為例如0至約95wt%或為約15至約45wt%。
在本揭示範圍內的具有三(3)或更多個活性胺
氫之多官能基胺的非限制性實例包括但不侷限於脂族胺、環脂族胺、芳族胺、聚(環氧烷)二胺或三胺；脂族胺、環脂族胺、或芳族胺之曼尼希鹼衍生物；具有二聚物脂肪酸或二聚物脂肪酸和脂肪酸之混合物的脂族胺、環脂族胺、或芳族胺之聚醯胺衍生物；具有脂肪酸的脂族胺、環脂族胺、或芳族胺之醯胺基胺衍生物；具有雙酚A或雙酚F之環氧丙基醚或環氧酚醛清漆樹脂的脂族胺、環脂族胺、或芳族胺之胺加成物衍生物等、或其任何組合。
多於一種多官能基胺可用於本揭示之組成物中。例如，該至少一種多官能基胺可包含脂族胺及環脂族胺之曼尼希鹼衍生物。又，該至少一種多官能基胺可包含一種脂族胺及一種不同的脂族胺。
範例脂族胺包括聚伸乙基胺(EDA、DETA、TETA、TEPA、PEHA等)、聚伸丙基胺、胺基丙基化乙二胺(Am3、Am4、Am5等)、胺基丙基化丙二胺、1,6-己二胺、3,3,5-三甲基-1,6-己二胺、3,5,5-三甲基-1,6-己二胺、2-甲基-1,5-戊二胺等、或其組合。在本發明一態樣中，該至少一種多官能基胺為EDA、DETA、TETA、TEPA、PEHA、丙二胺、二伸丙基三胺、三伸丙基四胺、N-3-胺基丙基乙二胺(Am3)、N,N'-雙(3-胺基丙基)乙二胺(Am4)、N,N,N'-參(3-胺基丙基)乙二胺(Am5)、N-3-胺基丙基-1,3-二胺基丙烷、N,N'-雙(3-胺基丙基)-1,3-二胺基丙烷、N,N,N'-參(3-胺基丙基)-1,3-二胺基丙烷、或其任何組合。另外，由Huntsman Corporation以商標JEFFAMINE®銷售的
聚(環氧烷)二胺及三胺可用於本發明。說明實例包括但不侷限於JEFFAMINE® D-230、JEFFAMINE® D-400、JEFFAMINE® D-2000、JEFFAMINE® D-4000、JEFFAMINE® T-403、JEFFAMINE® EDR-148、JEFFAMINE® EDR-192、JEFFAMINE® C-346、JEFFAMINE® ED-600、JEFFAMINE® ED-900、JEFFAMINE® ED-2001等、或其組合。環脂族及芳族胺包括但不侷限於1,2-二胺基環己烷、1,3-二胺基環己烷、1,4-二胺基環己烷、胺基丙基環己胺(APCHA)、氫化鄰甲苯二胺、氫化偏甲苯二胺、偏伸茬基二胺、氫化偏伸茬基二胺(商業上稱為1,3-BAC)、異佛酮二胺、降莰烷二胺、3,3'-二甲基-4,4'-二胺基二環己基甲烷、4,4'-二胺基二環己基甲烷、2,4'-二胺基二環己基甲烷、亞甲基橋接之聚(環己基-芳族)胺的混合物等、或其組合。亞甲基橋接之聚(環己基-芳族)胺的混合物係縮寫為MBPCAA或MPCA，且描述於美國專利5,280,091號，該案係以全文引用方式併入本文中。在本揭示之一態樣中，該至少一種多官能基胺為亞甲基橋接之聚(環己基-芳族)胺的混合物(MPCA)。
曼尼希鹼衍生物可藉由上述脂族胺、環脂族胺、或芳族胺與酚或經取代之酚及甲醛或聚甲醛的反應製成。用於製造可用於本揭示之曼尼希鹼的範例經取代之酚為腰果酚(cardanol)，其係自腰果殼液體獲得。或者，曼尼希鹼可藉由多官能基胺與含曼尼希鹼之三級胺(諸如參-二甲胺基甲基酚(市售者為Air Products and Chemicals,
Inc.之ANCAMINE® K-5)或雙-二甲胺基甲基酚)的交換反應所製備。聚醯胺衍生物可藉由脂族胺、環脂族胺、或芳族胺與二聚物脂肪酸、或二聚物脂肪酸與脂肪酸之混合物反應所製備。醯胺基胺衍生物可藉由脂族胺、環脂族胺、或芳族胺與脂肪酸之反應所製備。胺加成物可藉由脂族胺、環脂族胺、聚醯胺、或芳族胺與環氧樹脂之反應，例如與雙酚-A之二環氧丙基醚、雙酚-F之二環氧丙基醚、或環氧酚醛清漆樹脂之反應所製備。脂族、環脂族、聚醯胺及芳族胺亦可與單官能基環氧樹脂(諸如苯基環氧丙基醚、甲苯酚基環氧丙基醚、丁基環氧丙基醚、其他烷基環氧丙基醚等)加成。
在本揭示之特定實施態樣中，隨意的(iv)改質劑係包括在環氧固化劑中。該隨意的(iv)改質劑可為與可固化環氧系組成物可相容之任何非反應性組分。例如，該改質劑可稀釋、加速及/或韌化該環氧固化劑。適用之改質劑包括但不侷限於苯甲醇、糠醇、聚乙二醇、及其組合。(iv)改質劑在該環氧固化劑中之組成範圍可為例如0至約50wt%或為約5至約40wt%。
在本揭示之特定實施態樣中，隨意的(v)丙烯酸酯係包括在可固化環氧系組成物中。適用之(v)丙烯酸酯可包括單官能基、二官能基、多官能基丙烯酸酯及具有丙烯酸酯端基之任何聚合物。此等丙烯酸酯經由比環氧樹脂-胺加成反應具有更高反應性之Michael加成反應而與胺基反應。該(v)丙烯酸酯在可固化環氧系組成物中可作為
可固化樹脂、稀釋劑及/或增韌劑。適用之(v)丙烯酸酯包括但不侷限於丙烯酸月桂酯(LA)、二丙烯酸1,6-己二醇酯(HDDA)、三羥甲基丙烷三丙烯酸酯(TMPTA)、聚(環氧烷)二丙烯酸酯、聚胺甲酸酯二丙烯酸酯(PUDA)、聚酯二丙烯酸酯及其組合。(v)丙烯酸酯在該環氧樹脂中之組成範圍可為例如0至100wt%或為約10至約60wt%。
在本發明又另一態樣中，形成固化環氧樹脂之方法包括混合根據本揭示的可固化環氧系組成物。本揭示之環氧組成物包含固化劑組成物和包含至少一種環氧樹脂之環氧組成物的接觸產物。一種適用之環氧樹脂種類為多官能基環氧樹脂。如本文所使用之多官能基環氧樹脂描述每分子含有2或更多個1,2-環氧基之化合物。此種類之環氧化物化合物為熟習本領域之人士熟知，且係說明於Y.Tanaka之"Synthesis and Characteristics of Epoxides"，於C.A.May編之Epoxy Resins Chemistry and Technology(Marcel Dekker,1988)，其係以全文引用方式併入本文中。
用語「接觸產物」在本文中係用以描述其中組分係以任何順序、任何方式及例如時間長度接觸的組成物。例如，該等組分係藉由摻合或混合接觸。此外，任何組分之接觸可在存在或不存在本文所述之組成物或調配物的任何其他組分之下發生。又另外的，該接觸產物之組分的二或更多者可反應形成反應產物以及其他組分，該等其他組分進一步反應以使化合物包含該組成物。組合其他材
料或組分可藉由熟習本領域之人士已知的方法進行。
環氧組成物之所選擇相對量與固化劑組成物、或硬化劑之所選擇相對量可視例如最終用途物件、其所希望性質、及用以製造該最終用途物件的製造方法及條件而變化。例如，在使用特定環氧組成物之塗料應用中，併入相對於固化劑組成物之數量較大量的環氧樹脂會造成乾燥時間增加，但伴隨硬度提高以及以光澤測量之經改良外觀的塗料。在一些黏著劑應用中，將使用較多固化劑以改善固化速度或可撓性。本揭示之環氧組成物通常具有環氧組成物中之環氧基對固化劑組成物中之胺氫的化學計量比在約1.5：1至約0.5：1之範圍。例如，此等環氧組成物可具有如下之化學計量比：約1.5：1、約1.4：1、約1.3：1、約1.2：1、約1.1：1、約1：1、約0.9：1、約0.8：1、或約0.7：1、或約0.6：1、或約0.5：1。在另一態樣中，該化學計量比在約1.3：1至約0.6：1之範圍。在又另一態樣中，該化學計量比在約1.2：1至約0.6：1之範圍。在又另一態樣中，該化學計量比在約1.1：1至約0.9：1之範圍。
適用於本揭示之一種環氧樹脂類別包含多元酚之環氧丙基醚，包括二元酚之環氧丙基醚。說明實例包括但不侷限於下列之環氧丙基醚：間苯二酚、氫醌、雙-(4-羥基-3,5-二氟苯基)-甲烷、1,1-雙-(4-羥基苯基)-乙烷、2,2-雙-(4-羥基-3-甲基苯基)-丙烷、2,2-雙-(4-羥基-3,5-二氯苯基)丙烷、2,2-雙-(4-羥基苯基)-丙烷(市售已知為雙酚A)、雙-(4-羥基苯基)-甲烷(市售已知為雙酚F，且其可含
有不同量之2-羥基苯基異構物)等、或其任何組合。另外，具有下列結構之升級二元酚亦可用於本揭示：
其中m為整數，且R1為二元酚(諸如前文所列之二元酚)的二價烴基。根據該式之材料可藉由將二元酚與表氯醇之混合物聚合、或藉由將二元酚之二環氧丙基醚的混合物升級所製備。雖然在任何給定分子中之m值為整數，但該等材料為可以m之平均值表示特徵的不變混合物，其中該m不一定為整數。m之平均值介於0與約7的聚合材料可用於本揭示之一態樣中。
在另一態樣中，為酚醛清漆樹脂之環氧丙基醚的環氧酚醛清漆樹脂可用作根據本揭示之多官能基環氧樹脂。在又一另外態樣中，該至少一種多官能基環氧樹脂為雙酚-A之二環氧丙基醚(DGEBA)、DGEBA之升級或更高分子量變型、雙酚-F之二環氧丙基醚、環氧酚醛清漆樹脂、或其任何組合。DGEBA之更高分子量變型或衍生物係藉由升級方法製備，在該升級方法中將過量DGEBA與雙酚-A反應以產生環氧基封端之產物。此等產物之環氧化物當量(EEW)範圍為約450至3000或更高。由於此等產物在室溫下為固體，其經常稱為固體環氧樹脂。
DGEBA或升級之DGEBA樹脂因其低成本及通常高性能性質的組合而經常用於塗料調配物。EEW範圍為
約174至約250，及更常為約185至約195之商業級DGEBA相當容易取得。在此等低分子量情況下，該等環氧樹脂為液體，且經常稱為液體環氧樹脂。熟習本領域之人士暸解大部分液體環氧樹脂等級均輕度聚合，此係因純DGEBA具有的EEW為174之故。具有介於250與450之EEW的樹脂(亦通常藉由升級方法製備者)係稱為半固體環氧樹脂，原因係彼等為在室溫下為固體及液體的混合物。通常，具有基於固體計為約160至約750之EEW的多官能基樹脂可用於本發明。在另一態樣中，該多官能基環氧樹脂具有在約170至約250之範圍的EEW。
視最終用途應用而定，藉由改質環氧組分降低本揭示之組成物的黏度會是有益的。例如，可將黏度降低以使調配物或組成物中之顏料的含量增加同時仍容許容易施加，或使得能使用更高分子量之環氧樹脂。如此，該包含至少一種多官能基環氧樹脂之環氧組分係在本揭示範圍內以進一步包含單官能基環氧化物。單環氧化物之實例包括但不侷限於苯環氧乙烷、環氧環己烷、環氧乙烷、環氧丙烷、環氧丁烷；及酚、甲酚、第三丁苯酚、其他烷基酚、丁醇、2-乙基己醇、C4至C14醇之環氧丙基醚等、或其組合。該多官能基環氧樹脂亦可存在於溶液或乳液中，其中稀釋劑為水、有機溶劑、或其混合物。
本揭示之組成物可用以製造各種不同製造物件。視該物件之製造期間的要求或其最終用途應用之要求而定，調配物及組成物中可使用各種不同添加劑以訂製特
殊性質。此等添加劑包括但不侷限於溶劑(包括水)、加速劑、塑化劑、填料、纖維(諸如玻璃纖維或碳纖維)、顏料、顏料分散劑、流變性改質劑、搖變減黏膠、流動或整平助劑、界面活性劑、消泡劑、殺生物劑、或其任何組合。應暸解，本技術中已知之其他混合物或材料可包括在該等組成物或調配物中，且係在本揭示之範疇內。
本揭示亦關於包含本文所揭示之組成物的製造物件。例如，物件可包含含有固化劑組成物與環氧組成物之反應產物的環氧組成物。自本文所揭示之環氧組成物所製造的製造物件包括但不侷限於黏著劑、複合材料、電子設備、塗料、底漆、密封劑、固化混料、建築產品、地板產品、及複合產品。此外，此等黏著劑、塗料、底漆、密封劑、或固化混料可施加至金屬或膠結性基板。基於此等環氧組成物之塗料可為無溶劑或可視特定應用需要而含有稀釋劑，諸如水或有機溶劑。塗料可含有各種種類及含量之顏料以用於油漆及底漆應用。環氧塗布組成物包含厚度範圍為40至400μm(微米)，較佳為80至300μm，更佳為100至250μm之層，以用於施加至金屬基板上之保護塗料。此外，就用於地板產品或建築產品而言，塗布組成物包含厚度範圍為50至10,000μm之層，視產品種類及所需之最終性質而定。提供有限機械及化學抗性之塗料產品包含厚度範圍為50至500μm，較佳為100至300μm之層；然而諸如例如提供高機械及化學抗性之自整平地板的塗料產品包含厚度範圍為1,000至10,000μm，較佳為1,500至
5,000μm之層。
如熟習本領域之人士所熟知，眾多基板適於具有適當表面製備之本揭示黏著劑、塗料或密封劑的應用。此等基板包括但不侷限於混凝土及各種種類之金屬及合金，諸如鋼及鋁。本揭示之塗料適合大型金屬物品或膠結性基板(包括船、橋、工業廠房及設備、及地板)之油漆及塗布。
本發明之塗料可藉由任何數目之技術施加，包括噴塗、刷塗、滾塗、手套塗布(paint mitt)等。為了施加非常高固體含量或100%固體之本揭示塗料，可使用多組分噴塗施加設備，其中胺與環氧組分係在導至噴槍之管線中混合、在噴槍本身中混合、或藉由在兩種組分離開噴槍時將彼等混合在一起。使用該技術可減緩關於調配物之適用期的限制，該適用期通常隨著胺反應性及固體含量增加二者而縮短。經加熱之多組分設備可用以降低該等組分的黏度，從而改善施加容易度。
建築及地板應用包括包含本揭示之環氧組成物與混凝土或常用於建築產業之其他材料組合的組成物。本揭示之組成物的應用包括但不侷限於組成物用作底漆、深層穿透底漆、塗料、固化混料、及/或新或舊混凝土之密封劑，諸如ASTM C309-97(其係以引用方式併入本文中)所提及者的用途。作為底漆或密封劑，本揭示之環氧組成物可在施加塗料之前施加至表面以改善黏著劑接合。因其關於混凝土及膠結性應用，塗料為用於施加在表面上以產
生保護或裝飾層或表層的用劑。裂縫注射及裂縫填充產品亦可自本文所揭示之組成物製備。本揭示之環氧組成物可與膠結性材料(諸如混凝土混合物)混合以形成聚合物或經改質之水泥、磁磚填縫劑(tile grout)等。包含本文所揭示之環氧組成物的複合產品或物件的非限制性實例包括網球拍、滑雪板、自行車架、飛機機翼、玻璃纖維強化之複合材料、及其他模製產品。
在本揭示之特別用途中，該等固化劑組成物將在製造樹脂轉注成型複合材料(諸如輕量汽車零件)、灌注複合材料(諸如風車葉片)、航太黏著劑、工業黏著劑、以及其他相關應用中具有適用性。複合材料係由不同物質製成的材料，且在樹脂技術之情況下，複合材料係指浸漬樹脂之系統，其中該樹脂係藉由添加強化材料(諸如填料及纖維來強化以改善所得產品的一般性質。此等材料一起發揮作用但不彼此互溶。在本情況下，黏合劑組分包含環氧樹脂及環氧固化劑。有許多種類之複合材料應用，諸如預浸體、積層物、長絲纏繞、編織、拉擠、濕式積層及灌注複合材料。樹脂灌注、或樹脂轉注係藉以將前驅物導入複合材料模具中之方法，在前驅物導入之前強化材料已置入該模具中並關閉。該方法、有許多變型，諸如，真空輔助或高壓射出者。熱快速固化組成物將藉由縮短循環時間而促進複合材料之製造。
用胺系固化劑固化、硬化、及/或交聯之環氧樹脂的用途係為人熟知。此等環氧材料廣泛用於塗料範圍
之許多應用，其中彼等材料可用於各種不同應用，諸如底漆、黏結塗層(tie-coat)、及最後加工。彼等可施加於許多基板上。彼等可用於積層物、黏著劑、地板、無塵最後加工、二次圍阻、襯料、強化物、修補調配物、工具、封裝(potting)、及澆鑄。彼等可用於許多產業，如工業設備(維護及修補)、汽車(零件接合、複合材料製造)、電子(晶圓背貼式接合(wafer back bonding)、印刷電路基底、電子組件之封裝、線絕緣、部件固定器)、消費者(DIY黏著劑、傢俱修補、快速固定封口機)、運動(網球拍、高爾夫球桿、獨木舟、滑雪板)、海洋應用(零件接合或快速修補)、航空(零件膠合、用於艙室結構之蜂巢式強化、衛星重返大氣層之防護)、及更多其他應用，諸如用於貨櫃及儲槽之長絲纏繞、用於風能之積層物及用於飛機之螺旋槳、複合微球泡材(syntactic foam)、以及為熟習本領域之人士熟知的許多其他應用。
本揭示亦包括包含如上述之環氧組成物的製造物件。此等物件可包括但不侷限於黏著劑、塗料、底漆、密封劑、固化混料、建築產品、地板產品、複合產品、積層物、封裝化合物、填縫劑、填料、膠結性填縫劑、或自整平地板。額外組分或添加劑可與本揭示之組成物一起使用以生產製造物件。此外，此等塗料、底漆、密封劑、固化混料或填縫劑可施加至金屬或膠結性基板。
本揭示進一步藉由下列實施例說明，該等實施例不應解釋為對本發明範圍加上限制。在閱讀本文說明
之後，在不脫離本揭示精神或附錄申請專利範圍的範疇的情況下，各種其他態樣、實施態樣、修改及其等效物會使熟習本領域之人士想起其本身。
提供下列合成實施例以說明本發明之特定態樣或實施態樣，且不應使附錄之申請專利範圍的範疇侷限於此。
將1莫耳之胺及60ml之正丁醇裝至具備頂部機械攪拌器、氮入口、滴液漏斗及熱電偶之四頸圓底燒瓶。攪拌反應物並用高純度氮吹掃0.5小時。之後，將1莫耳溶解於200-mL之正丁醇的酸緩慢滴入以維持在滴入期間溫度不高於70℃。該反應進一步在80℃進行2小時，然後逐漸提高溫度至110℃，與此同時施加真空以蒸餾正丁醇及自p-TSA涉入的水。在高度真空下保持1至2小時之後，收集樣本並進行水含量測試。一旦水含量符合規格，將所得之胺鹽冷卻至室溫，並獲得黏稠黃色液體。
將149g之四伸乙五胺(TEPA)及40ml之正丁醇裝至具備頂部機械攪拌器、氮入口、滴液漏斗及熱電偶之四頸圓底燒瓶。攪拌反應物並用高純度氮吹掃0.5小時。
之後，將150g之溶解於160-mL之正丁醇的對甲苯磺酸(p-TSA)緩慢滴入以維持溫度不高於70℃。該反應進一步在80℃進行2小時，然後逐漸提高溫度至110℃，與此同時施加真空以蒸餾正丁醇及自p-TSA涉入的水。在高度真空下保持1至2小時之後，收集樣本並進行水含量測試。一旦水含量符合規格(即，低於1%)，將所得之胺鹽冷卻至室溫，並獲得黏稠螢光黃液體。
實施例2依照實施例1之製程，但348.6g之五伸乙六胺(PEHA)與285.2g之對甲苯磺酸(p-TSA)H2O在作為溶劑之正丁醇存在下反應，且得到黏稠棕色液體。
實施例3依照實施例1之製程，但261.4g之N,N'-雙(3-胺基丙基)乙二胺(Am4)與285.2g之p-TSA.H2O在作為溶劑之正丁醇存在下反應，且得到黏稠淺色液體。
實施例4依照實施例1之製程，但261.4g之Am4與207.0g之柳酸(SA)在作為溶劑之正丁醇存在下反應，且形成具有中等黏度(即，1,000至10,000cps)之淺色液體。
實施例5依照實施例1之製程，但261.4g之Am4與225.1g之三氟甲磺酸(TFMSA)在作為溶劑之正丁醇存在下反應，且得到具有中等黏度之淺色液體。
提供由72份實施例1及28份苯甲醇所製成的環氧固化劑。ANCAMINE® 1637Iv及ANCAMINE® 1767用於對照實例(可得自Air Products & Chemicals,Inc.)。結果示於表2。
提供由72份之實施例3及28份之AMICURE PACM構成的固化劑。AMICURE PACM為Air Products & Chemicals,Inc.之商標，視同PACM。結果示於表3及圖1。
圖1顯示實施例7藉由DSC之等溫掃描。為了進行實施例7之藉由DSC的掃描，雙酚A二環氧丙基醚DER 331係與固化劑混合，然後藉由DSC(TA Instruments QA2000)使用跳升至120℃然後等溫15分鐘之程式予以分析。使用上述相同程式掃描實施例7之固化樣本，並用作基線檔案。
使用ASTM標準方法測定膠凝時間、搭接剪強度(lap share strength)以及拉伸性質，如表4所列。膠凝時
間表示組成物從液體過渡為凝膠的時間之特徵。胺-環氧組成物之膠凝時間係使用ASTM D2471，採用TECHNE膠凝計時器FGT 6型測量。搭接剪試樣係根據ASTM D1002製備，用於LSS之基板係經磨砂之冷軋鋼，且十字頭速度為2mm/min。拉伸試樣係根據ASTM D638製備。
雖然已參考特定態樣或實施態樣說明本發明，但可了解熟習本領域之人士會暸解在不違背本發明範圍情況下可進行各種改變且等效物可被其元件取代。此外，在不違背本發明基本範圍的情況下，已做出許多修改以適應本發明教示。因此，希望本發明不侷限於已揭示欲為進行本發明之最佳模式的特定實施態樣，而是本發明包括在附錄申請專利範圍範疇之內的所有實施態樣。
Claims (19)
- 一種環氧固化劑，其包含至少一種室溫離子液體鹽，該室溫離子液體鹽為下列之反應產物：(a)至少一種以式(I)表示之聚伸烷基多胺(polyalkylene polyamine)化合物：
- 如申請專利範圍第1項之環氧固化劑，其中，該至少一種聚伸烷基多胺化合物為不同聚伸烷基多胺化合物之混合物。
- 如申請專利範圍第1項之環氧固化劑，其中，該至少一種聚伸烷基多胺化合物為聚伸烷基多胺之衍生物。
- 如申請專利範圍第1項之環氧固化劑，其中，該聚伸 烷基多胺之衍生物為選自下列之一或多種化合物：烷基化聚伸烷基多胺、苯甲基化聚伸烷基多胺、羥烷基化聚伸烷基多胺、及聚伸烷基多胺加成物。
- 如申請專利範圍第1項之環氧固化劑，在形成該反應產物的反應混合物中之組分(b)對組分(a)的莫耳比為大於0至1.8。
- 如申請專利範圍第1項之環氧固化劑，在形成該反應的反應混合物中之組分(b)對組分(a)的莫耳比為0.3至1.3。
- 如申請專利範圍第1項之環氧固化劑，其進一步包括第二胺，該第二胺為一級胺、二級胺、三級胺、四級胺、或其衍生物。
- 如申請專利範圍第7項之環氧固化劑，其中，該第二胺為選自由下列所組成之群組的化合物：胺基乙基哌、異佛酮二胺、4,4'-亞甲基雙(環己胺)、醚胺(Ether amine)、及其組合。
- 一種可固化環氧系組成物，其包含：(i)至少一種環氧樹脂；以及(ii)環氧固化劑，其包含至少一種室溫離子液體鹽，該室溫離子液體鹽為下列之反應產物： (a)至少一種以式(I)表示之聚伸烷基多胺化合物：
- 如申請專利範圍第9項之可固化環氧系組成物，其中，該至少一種環氧樹脂包含選自由下列所組成之群組的化合物：雙酚A二環氧丙基醚、雙酚F二環氧丙基醚、及環氧酚醛清漆(epoxy novolac)。
- 如申請專利範圍第9項之可固化環氧系組成物，其進一步包括(iii)第二胺，該第二胺為一級胺、二級胺、三級胺、四級胺、或其衍生物。
- 如申請專利範圍第11項之可固化環氧系組成物，其中，該(iii)第二胺為選自由下列所組成之群組的化合物：胺基乙基哌、異佛酮二胺、4,4'-亞甲基雙(環己胺)、醚胺、及其組合。
- 如申請專利範圍第9項之可固化環氧系組成物，其進一步包括(vi)至少一種選自由下列所組成之群組的改質劑：苯甲醇、糠醇、聚乙二醇及其組合。
- 如申請專利範圍第13項之可固化環氧系組成物，其進一步包括(v)丙烯酸酯。
- 如申請專利範圍第14項之可固化環氧系組成物，其中，該(v)丙烯酸酯係選自由下列所組成之群組：丙烯酸月桂酯、二丙烯酸1,6-己二醇酯、三羥甲基丙烷三丙烯酸酯、聚(環氧烷)二丙烯酸酯(poly(alkylene oxide)diacrylate)、聚胺甲酸酯二丙烯酸酯及其組合。
- 一種用於形成固化環氧樹脂(cured epoxy)之方法，其包括混合如申請專利範圍第9項之可固化環氧系組成物。
- 一種固化環氧樹脂，其包括如申請專利範圍第9項之可固化環氧系組成物的接觸產物。
- 一種固化物件，其係自如申請專利範圍第9項之組成物製得。
- 如申請專利範圍第18項之固化物件，其中，該物件為 黏著劑、塗料、底漆、密封劑、固化混料、建築產品、地板產品、或複合產品。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2016/087248 WO2018000125A1 (en) | 2016-06-27 | 2016-06-27 | Room temperature ionic liquid curing agent |
| ??PCT/CN2016/087248 | 2016-06-27 | ||
| WOPCT/CN2016/087248 | 2016-06-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201815870A TW201815870A (zh) | 2018-05-01 |
| TWI752973B true TWI752973B (zh) | 2022-01-21 |
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| TW106121137A TWI752973B (zh) | 2016-06-27 | 2017-06-23 | 作為快速環氧固化劑之室溫離子液體 |
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| US (2) | US20190330412A1 (zh) |
| EP (1) | EP3475330B1 (zh) |
| JP (1) | JP6921134B2 (zh) |
| KR (1) | KR102586629B1 (zh) |
| CN (1) | CN109415488B (zh) |
| TW (1) | TWI752973B (zh) |
| WO (1) | WO2018000125A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3569630B1 (de) | 2018-05-17 | 2022-08-03 | Evonik Operations GmbH | Schnell härtende epoxysysteme |
| US11286335B2 (en) | 2018-05-17 | 2022-03-29 | Evonik Operations Gmbh | Fast-curing epoxy systems |
| US11359048B2 (en) | 2018-05-17 | 2022-06-14 | Evonik Operations Gmbh | Fast-curing epoxy systems |
| EP3569629B1 (de) | 2018-05-17 | 2022-07-06 | Evonik Operations GmbH | Schnell härtende epoxysysteme |
| US20210221971A1 (en) * | 2018-08-21 | 2021-07-22 | Evonik Operations Gmbh | Fast curing epoxy system for producing rigid foam and use of the foam in composites or as insulation material |
| CN109608893B (zh) * | 2018-12-04 | 2020-12-08 | 河南省交通规划设计研究院股份有限公司 | 桥面防水粘结层用废胎胶粉沥青材料及其制备方法 |
| FR3091406B1 (fr) * | 2018-12-31 | 2021-01-15 | Centre National De Recherche Scient Cnrs | Matériau pour l’isolation électrique et procédé de fabrication |
| CN110240693B (zh) * | 2019-07-10 | 2021-12-17 | 深圳市前海博扬研究院有限公司 | 多胺固化剂及制备方法和环氧树脂组合物 |
| CN114605907B (zh) * | 2022-01-27 | 2023-03-28 | 北京东方雨虹防水技术股份有限公司 | 一种聚氨酯防水涂料 |
| CN116178677A (zh) * | 2022-12-16 | 2023-05-30 | 浙江博菲电气股份有限公司 | 一种新型羧酸类环氧树脂固化剂及其制备方法与应用 |
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| US4229563A (en) * | 1979-08-03 | 1980-10-21 | Ameron, Inc. | Aromatic amidoamines |
| US20110152448A1 (en) * | 2009-12-18 | 2011-06-23 | Hexion Specialty Chemicals, Inc. | Epoxy resin curing compositions and epoxy resin systems including same |
| CN103974993A (zh) * | 2011-12-01 | 2014-08-06 | 陶氏环球技术有限责任公司 | 用于硬化剂的液体促进剂组合物 |
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| US4264758A (en) * | 1979-11-02 | 1981-04-28 | Texaco Development Corporation | Novel epoxy curing system |
| US5426157A (en) * | 1994-03-16 | 1995-06-20 | Air Products And Chemicals, Inc. | Flexibilized polyepoxide resins incorporating poly-N-methylated secondary amines |
| US5618905A (en) * | 1995-04-11 | 1997-04-08 | Air Products And Chemicals, Inc. | Partially methylated polyamines as epoxy curing agents |
| KR20000062383A (ko) * | 1996-12-31 | 2000-10-25 | 오노 알버어스 | 주위 이하의 온도에서 자가 경화성 에폭시 수지에 대한 저장안정성 상용성 경화제 조성물 |
| US6911109B2 (en) * | 2000-12-11 | 2005-06-28 | Henkel Corporation | Two-part, room temperature curable epoxy resin/ (meth)acrylate compositions and process for using same to bond substrates |
| JP2002226554A (ja) * | 2001-01-31 | 2002-08-14 | Otsuka Chem Co Ltd | エポキシ樹脂用硬化促進剤及びエポキシ樹脂用硬化剤組成物 |
| ATE307153T1 (de) * | 2001-08-28 | 2005-11-15 | Resolution Res Nederland Bv | Niederviskose härterzusammensetzungen in epoxidharzsystemen für tieftemperaturhärtungsanwendungen |
| JP2007204532A (ja) * | 2006-01-31 | 2007-08-16 | Adeka Corp | エポキシ樹脂用硬化剤組成物及び該エポキシ樹脂用硬化剤組成物を含有してなる硬化性エポキシ樹脂組成物 |
| US8518547B2 (en) * | 2007-02-07 | 2013-08-27 | Air Products And Chemicals, Inc. | Alkylated polyalkylene polyamines and uses thereof |
| US8519091B2 (en) * | 2007-04-10 | 2013-08-27 | Air Products And Chemicals, Inc. | Polyalkyleneamine adducts as curing agents for thick layer water-based epoxy systems |
| JP2011032278A (ja) * | 2010-10-06 | 2011-02-17 | Idemitsu Kosan Co Ltd | アミド化合物及びその用途 |
| CN102432830B (zh) * | 2011-08-02 | 2013-04-10 | 华南理工大学 | 一种水性环氧树脂固化剂乳液及其制备方法 |
| EP2592100A1 (de) | 2011-11-10 | 2013-05-15 | Sika Technology AG | Härter für epoxidharz-beschichtungen |
| KR20160140605A (ko) * | 2014-03-28 | 2016-12-07 | 훈츠만 어드밴스트 머티리얼스 라이센싱 (스위처랜드) 게엠베하 | 섬유 강화된 에폭시 복합 물품의 제조 방법, 얻어진 복합 물품 및 그의 용도 |
-
2016
- 2016-06-27 KR KR1020197002486A patent/KR102586629B1/ko active Active
- 2016-06-27 US US16/309,154 patent/US20190330412A1/en not_active Abandoned
- 2016-06-27 WO PCT/CN2016/087248 patent/WO2018000125A1/en not_active Ceased
- 2016-06-27 CN CN201680087165.4A patent/CN109415488B/zh active Active
- 2016-06-27 EP EP16906529.9A patent/EP3475330B1/en active Active
- 2016-06-27 JP JP2018567838A patent/JP6921134B2/ja active Active
-
2017
- 2017-06-23 TW TW106121137A patent/TWI752973B/zh active
-
2022
- 2022-07-18 US US17/867,220 patent/US12247097B2/en active Active
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US4229563A (en) * | 1979-08-03 | 1980-10-21 | Ameron, Inc. | Aromatic amidoamines |
| US20110152448A1 (en) * | 2009-12-18 | 2011-06-23 | Hexion Specialty Chemicals, Inc. | Epoxy resin curing compositions and epoxy resin systems including same |
| CN103974993A (zh) * | 2011-12-01 | 2014-08-06 | 陶氏环球技术有限责任公司 | 用于硬化剂的液体促进剂组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109415488A (zh) | 2019-03-01 |
| US12247097B2 (en) | 2025-03-11 |
| US20190330412A1 (en) | 2019-10-31 |
| EP3475330B1 (en) | 2020-08-05 |
| JP2019525975A (ja) | 2019-09-12 |
| EP3475330A1 (en) | 2019-05-01 |
| EP3475330A4 (en) | 2019-12-11 |
| KR20190022758A (ko) | 2019-03-06 |
| CN109415488B (zh) | 2022-04-29 |
| TW201815870A (zh) | 2018-05-01 |
| JP6921134B2 (ja) | 2021-08-18 |
| KR102586629B1 (ko) | 2023-10-11 |
| WO2018000125A1 (en) | 2018-01-04 |
| US20220356298A1 (en) | 2022-11-10 |
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