JP7407955B2 - エポキシ樹脂組成物用のジアミノメチルシクロヘキサンおよび1,3-シクロヘキサンビス(メチルアミン)に基づく硬化剤組成物、エポキシ樹脂組成物、ならびに多成分エポキシ樹脂系 - Google Patents
エポキシ樹脂組成物用のジアミノメチルシクロヘキサンおよび1,3-シクロヘキサンビス(メチルアミン)に基づく硬化剤組成物、エポキシ樹脂組成物、ならびに多成分エポキシ樹脂系 Download PDFInfo
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- JP7407955B2 JP7407955B2 JP2022543710A JP2022543710A JP7407955B2 JP 7407955 B2 JP7407955 B2 JP 7407955B2 JP 2022543710 A JP2022543710 A JP 2022543710A JP 2022543710 A JP2022543710 A JP 2022543710A JP 7407955 B2 JP7407955 B2 JP 7407955B2
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- epoxy resin
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- amine mixture
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- 239000000203 mixture Substances 0.000 title claims description 216
- 229920000647 polyepoxide Polymers 0.000 title claims description 113
- 239000003822 epoxy resin Substances 0.000 title claims description 111
- 239000003795 chemical substances by application Substances 0.000 title claims description 73
- OYOFUEDXAMRQBB-UHFFFAOYSA-N cyclohexylmethanediamine Chemical compound NC(N)C1CCCCC1 OYOFUEDXAMRQBB-UHFFFAOYSA-N 0.000 title claims description 26
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 title claims description 23
- 150000001412 amines Chemical class 0.000 claims description 75
- 150000003839 salts Chemical class 0.000 claims description 75
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 15
- 239000004848 polyfunctional curative Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 229910017604 nitric acid Inorganic materials 0.000 claims description 12
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 claims description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 6
- 150000001768 cations Chemical class 0.000 claims description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
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- 150000002823 nitrates Chemical class 0.000 claims 1
- 150000008648 triflates Chemical class 0.000 claims 1
- -1 polycyclic amines Chemical class 0.000 description 23
- 239000004570 mortar (masonry) Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 18
- 239000004567 concrete Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
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- 239000011575 calcium Substances 0.000 description 13
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
- 239000004593 Epoxy Substances 0.000 description 11
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- 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 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
- 238000010276 construction Methods 0.000 description 10
- 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 10
- 229910052500 inorganic mineral Inorganic materials 0.000 description 10
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- 239000002318 adhesion promoter Substances 0.000 description 8
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- 239000003085 diluting agent Substances 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 229920003319 Araldite® Polymers 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001450 anions Chemical class 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 230000002787 reinforcement Effects 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical compound OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910002651 NO3 Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 238000004873 anchoring Methods 0.000 description 4
- 239000011449 brick Substances 0.000 description 4
- 229910021485 fumed silica Inorganic materials 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 3
- 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 3
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 229910001963 alkali metal nitrate Inorganic materials 0.000 description 3
- 229910001964 alkaline earth metal nitrate Inorganic materials 0.000 description 3
- 230000001680 brushing effect Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
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- 238000002156 mixing Methods 0.000 description 3
- OMKZWUPRGQMQJC-UHFFFAOYSA-N n'-[3-(dimethylamino)propyl]propane-1,3-diamine Chemical compound CN(C)CCCNCCCN OMKZWUPRGQMQJC-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000007586 pull-out test Methods 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 3
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 2
- HCKPQGBXPQNMKU-UHFFFAOYSA-N 2,3-bis[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=CC(O)=C1CN(C)C HCKPQGBXPQNMKU-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical class CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- OHJDDRJXKMWSFJ-UHFFFAOYSA-N 2,4-diethyl-5-methylbenzene-1,3-diamine Chemical compound CCC1=C(C)C=C(N)C(CC)=C1N OHJDDRJXKMWSFJ-UHFFFAOYSA-N 0.000 description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
- HSDVRWZKEDRBAG-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COC(CCCCC)OCC1CO1 HSDVRWZKEDRBAG-UHFFFAOYSA-N 0.000 description 2
- ZHJGWYRLJUCMRT-UHFFFAOYSA-N 5-[6-[(4-methylpiperazin-1-yl)methyl]benzimidazol-1-yl]-3-[1-[2-(trifluoromethyl)phenyl]ethoxy]thiophene-2-carboxamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1C(C)OC(=C(S1)C(N)=O)C=C1N(C1=C2)C=NC1=CC=C2CN1CCN(C)CC1 ZHJGWYRLJUCMRT-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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- XZAHJRZBUWYCBM-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1(CN)CCCCC1 XZAHJRZBUWYCBM-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
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- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
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- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 2
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- 239000000080 wetting agent Substances 0.000 description 2
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- KFUSXMDYOPXKKT-VIFPVBQESA-N (2s)-2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OC[C@H]1OC1 KFUSXMDYOPXKKT-VIFPVBQESA-N 0.000 description 1
- UJFKWWYECHWRIC-UHFFFAOYSA-N (3-hydrazinyl-2-methyl-1-propylcyclohexyl)hydrazine Chemical compound NNC1(C(C(CCC1)NN)C)CCC UJFKWWYECHWRIC-UHFFFAOYSA-N 0.000 description 1
- LJEVRPSUZQQRQY-UHFFFAOYSA-N (3-hydrazinyl-4-methyl-1-propylcyclohexyl)hydrazine Chemical compound NNC1(CC(C(CC1)C)NN)CCC LJEVRPSUZQQRQY-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- YDIZFUMZDHUHSH-UHFFFAOYSA-N 1,7-bis(ethenyl)-3,8-dioxatricyclo[5.1.0.02,4]oct-5-ene Chemical compound C12OC2C=CC2(C=C)C1(C=C)O2 YDIZFUMZDHUHSH-UHFFFAOYSA-N 0.000 description 1
- WEIVEBIRFQGROM-UHFFFAOYSA-N 1-n-(2-aminoethyl)propane-1,2-diamine Chemical compound CC(N)CNCCN WEIVEBIRFQGROM-UHFFFAOYSA-N 0.000 description 1
- JOLVYUIAMRUBRK-UHFFFAOYSA-N 11',12',14',15'-Tetradehydro(Z,Z-)-3-(8-Pentadecenyl)phenol Chemical class OC1=CC=CC(CCCCCCCC=CCC=CCC=C)=C1 JOLVYUIAMRUBRK-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
- KCAMLFCTSSYIFW-UHFFFAOYSA-N 2,4,6-tris(dimethylamino)phenol Chemical compound CN(C)C1=CC(N(C)C)=C(O)C(N(C)C)=C1 KCAMLFCTSSYIFW-UHFFFAOYSA-N 0.000 description 1
- OEZORRJIKFZSAD-UHFFFAOYSA-N 2-(2,2,6,6-tetramethylpiperidin-4-yl)propane-1,3-diamine Chemical compound CC1(C)CC(C(CN)CN)CC(C)(C)N1 OEZORRJIKFZSAD-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
- VMSIYTPWZLSMOH-UHFFFAOYSA-N 2-(dodecoxymethyl)oxirane Chemical compound CCCCCCCCCCCCOCC1CO1 VMSIYTPWZLSMOH-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5026—Amines cycloaliphatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
- C08G59/245—Di-epoxy compounds carbocyclic aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
Description
「硬化剤組成物」は、アミン混合物の総重量に基づいて、5~50重量%のジアミノメチルシクロヘキサンおよび少なくとも25重量%の1,3-シクロヘキサンビス(メチルアミン)を有するアミン混合物と、少なくとも1種の塩(S)とを含む組成物である。
「芳香脂肪族化合物」は、官能化された芳香脂肪族化合物の場合、存在する官能基が化合物の芳香族部分ではなく脂肪族に結合しているような芳香族主鎖を有する脂肪族化合物であり、
「芳香族化合物」は、ヒュッケル則(4n+2)に従う化合物であり、
「アミン」は、1個、2個、または3個の水素原子を炭化水素基で置き換えることによってアンモニアから誘導され、一般構造RNH2(一級アミン)、R2NH(二級アミン)、およびR3N(三級アミン)を有する化合物であり(A.D.McNaught and A.Wilkinson,Blackwell Scientific Publications,Oxford(1997)によって編集されたIUPAC Compendium of Chemical Terminology,2nd ed.(the“Gold Book”)を参照されたい)、
「アミン混合物」は、少なくとも2つの異なるアミンの混合物を意味し、本発明による混合物は、アミン混合物の総重量に基づいて、5~50重量%のジアミノメチルシクロヘキサンおよび少なくとも25重量%の1,3-シクロヘキサンビス(メチルアミン)を含む。アミン混合物は、任意選択的に1つ以上のさらなるアミンを含有し得る。
「少なくとも1つ」は、数値的に「1つ以上」を意味し、好ましい実施形態では、この用語は、数値的に「1つ」を意味し、
「含有する」および「含む」は、言及された構成成分に加えて、より多くの構成成分が存在し得ることを意味し、これらの用語は、包括的であることを意味し、したがって、「からなる」も含み、「からなる」は、排他的に意味され、さらなる構成成分が存在しない場合があることを意味し、好ましい実施形態では、用語「含有する」および「含む」は、用語「からなる」を意味する。
このテキストで引用されたすべての標準(例えば、DIN標準)は、この出願の提出日に最新のバージョンで使用された。
最大Tg2を有するアミン/エポキシ樹脂混合物:4.65gのエポキシ樹脂を有する1gのアミン
原材料
実施例では、それぞれAraldite GY240およびAraldite GY282(Huntsman)の名称で市販されているビスフェノールA系およびビスフェノールF系エポキシ樹脂をエポキシ樹脂として使用した。
原材料
MGC社(Japan)からの1,3-シクロヘキサンジメタンアミン(1,3-BAC)およびm-キシリレンジアミン(mXDA)、ならびにBASF SE社(Germany)からのジアミノメチルシクロヘキサンの立体異性体混合物(MDACH、Baxxodur EC210)をアミンとして硬化剤組成物(B)の生成のために使用した。Huntsman社からのビスフェノールAジグリシジルエーテル(BADGE、Araldite GY240)も、以下のアミン付加物を合成するのに使用した。
58.75gのBaxxodur EC210および41.25gのAraldite GY240を室温で組み合わせ、24時間撹拌した。MDACH中のMDACH-BADGE付加物の溶液が得られた。
60.21gのm-キシリレンジアミンおよび39.79gのAraldite GY240を室温で組み合わせ、24時間撹拌した。mXDA中のmXDA-BADGE付加物の溶液が得られた。
EEWおよびAHEW値に従ってバランスのとれた化学量論をもたらす比のエポキシ樹脂成分(A)および硬化剤組成物(B)をスピード混合器で混合した。混合物を可能な限り気泡のない状態で1Kカートリッジに充填し、引き抜き試験のために調製した掘削孔に直ちに注入した。
R1:乾燥コンクリート、
ハンマードリル済み、
清浄:圧縮空気(6バール)で2回吹き出し、2回ブラッシングし、次いで再び圧縮空気(6バール)で2回吹き出す、
埋め込み深さ:60mm、
22℃で24時間の硬化、
B5(6時間):乾燥コンクリート
ハンマードリル済み
清浄:圧縮空気(6バール)で2回吹き出し、2回ブラッシングし、次いで再び圧縮空気(6バール)で2回吹き出す、
埋め込み深さ60mm、
22℃で6時間の硬化
B3、80℃:乾燥コンクリート、
ハンマードリル済み、
清浄:圧縮空気(6バール)で2回吹き出し、2回ブラッシングし、次いで再び圧縮空気(6バール)で2回吹き出す、
埋め込み深さ:60mm、
22℃で24時間硬化させ、次いで80℃で48時間保管する、
80±2℃でのアンカーロッドの引き抜き、
B8:水飽和コンクリート、
ハンマードリル済み、
圧縮空気(6バール)で1回吹き出し、1回ブラッシングし、次いで再び圧縮空気(6バール)で1回吹き出す、
注入:バッフルピンを有する混合器エクステンションを介して、水で満たされた掘削孔に注入する。
埋め込み深さ60mm、
22℃で48時間の硬化。
Claims (13)
- アミン混合物と、加速剤として少なくとも1種の塩(S)と含む硬化剤組成物であって、加速剤として使用される前記塩(S)が、硝酸の塩、亜硝酸の塩、ハロゲンの塩、トリフルオロメタンスルホン酸の塩、およびそれらの組み合わせからなる群から選択され、前記アミン混合物が、前記アミン混合物の総重量に基づいて、5~50重量%のジアミノメチルシクロヘキサンおよび少なくとも25重量%の1,3-シクロヘキサンビス(メチルアミン)を含むことを特徴とする、硬化剤組成物。
- 前記アミン混合物が、前記アミン混合物の総重量に基づいて、25~95重量%の1,3-シクロヘキサンビス(メチルアミン)を含むことを特徴とする、請求項1に記載の硬化剤組成物。
- 前記アミン混合物が、1,3-ベンゼンジメタンアミンをさらに含むことを特徴とする、請求項1または2のいずれかに記載の硬化剤組成物。
- 前記アミン混合物が、前記アミン混合物の総重量に基づいて、≦55重量%の1,3-ベンゼンジメタンアミンを含むことを特徴とする、請求項3に記載の硬化剤組成物。
- 前記アミン混合物が、前記硬化剤組成物の総重量に基づいて、30~98重量%の割合で前記硬化剤組成物に含有されることを特徴とする、請求項1~4のいずれかに記載の硬化剤組成物。
- 前記塩(S)が、前記硬化剤組成物の総重量に基づいて、0.1~15重量%の割合で前記硬化剤組成物に含有されることを特徴とする、請求項1~5のいずれかに記載の硬化剤組成物。
- 前記アミン混合物が、各々の場合で前記アミン混合物の総重量に基づいて、5~50重量%のジアミノメチルシクロヘキサン、30~80重量%の1,3-シクロヘキサンビス(メチルアミン)、および10~55重量%の1,3-ベンゼンジメタンアミンを含むことを特徴とする、請求項1~6のいずれかに記載の硬化剤組成物。
- 前記塩(S)が、硝酸塩(NO3 -)、ヨウ化物(I-)、トリフラート(CF3SO3 -)、およびそれらの混合物からなる群から選択されることを特徴とする、請求項1~7のいずれかに記載の硬化剤組成物。
- 前記塩(S)が、アルカリ金属、アルカリ土類金属、ランタノイド、アルミニウム、アンモニウム、およびそれらの組み合わせからなる群から選択されるカチオンを含むことを特徴とする、請求項1~8のいずれかに記載の硬化剤組成物。
- 少なくとも1つの硬化性エポキシ樹脂と、請求項1~9のいずれかに記載の硬化剤組成物とを含有する、エポキシ樹脂組成物。
- エポキシ樹脂成分(A)と、固化剤成分とを含む多成分エポキシ樹脂系であって、前記エポキシ樹脂成分(A)が、硬化性エポキシ樹脂を含有し、前記固化剤成分が、アミン混合物を含み、硝酸の塩、亜硝酸の塩、ハロゲンの塩、トリフルオロメタンスルホン酸の塩、およびそれらの組み合わせから選択される塩(S)が、前記エポキシ樹脂成分(A)および/または前記固化剤成分に含有され、前記アミン混合物が、前記アミン混合物の総重量に基づいて、5~50重量%のジアミノメチルシクロヘキサンおよび少なくとも25重量%の1,3-シクロヘキサンビス(メチルアミン)を含有することを特徴とする、多成分エポキシ樹脂系。
- 前記塩(S)が、前記固化剤成分に含有されることを特徴とする、請求項11に記載の多成分エポキシ樹脂系。
- 掘削孔内の構造的要素の化学的締結のための方法であって、請求項10に記載のエポキシ樹脂組成物、または請求項11もしくは12のいずれかに記載の多成分エポキシ樹脂系が、化学的締結のために使用される、方法。
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EP20163785.7 | 2020-03-18 | ||
EP20163785.7A EP3882294A1 (de) | 2020-03-18 | 2020-03-18 | Härterzusammensetzung auf basis von diaminomethylcyclohexan und 1,3-cyclo-hexan-bis(methylamin) für eine epoxidharzmasse, epoxidharzmasse und mehrkomponenten-epoxidharzsystem |
PCT/EP2021/055716 WO2021185607A1 (de) | 2020-03-18 | 2021-03-08 | Härterzusammensetzung auf basis von diaminomethylcyclohexan und 1,3- cyclo-hexan-bis(methylamin) für eine epoxidharzmasse, epoxidharzmasse und mehrkomponenten-epoxidharzsystem |
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CN115175949A (zh) | 2022-10-11 |
EP3882294A1 (de) | 2021-09-22 |
CN115175949B (zh) | 2024-03-19 |
EP4121474B1 (de) | 2024-02-07 |
US11787899B2 (en) | 2023-10-17 |
EP4121474A1 (de) | 2023-01-25 |
WO2021185607A1 (de) | 2021-09-23 |
CA3168894A1 (en) | 2021-09-23 |
KR20220155346A (ko) | 2022-11-22 |
JP2023511342A (ja) | 2023-03-17 |
US20230129206A1 (en) | 2023-04-27 |
AU2021238465A1 (en) | 2022-11-03 |
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