CA2828693C - Polyether hybrid epoxy curatives - Google Patents
Polyether hybrid epoxy curatives Download PDFInfo
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- CA2828693C CA2828693C CA2828693A CA2828693A CA2828693C CA 2828693 C CA2828693 C CA 2828693C CA 2828693 A CA2828693 A CA 2828693A CA 2828693 A CA2828693 A CA 2828693A CA 2828693 C CA2828693 C CA 2828693C
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- carbon atoms
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- 239000004593 Epoxy Substances 0.000 title description 28
- 239000004721 Polyphenylene oxide Substances 0.000 title description 9
- 229920000570 polyether Polymers 0.000 title description 9
- 239000000203 mixture Substances 0.000 claims abstract description 184
- 238000006243 chemical reaction Methods 0.000 claims abstract description 73
- 239000000758 substrate Substances 0.000 claims abstract description 34
- 238000000576 coating method Methods 0.000 claims abstract description 29
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 27
- 239000011248 coating agent Substances 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 18
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 11
- 238000007039 two-step reaction Methods 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 149
- 125000004432 carbon atom Chemical group C* 0.000 claims description 144
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 239000003607 modifier Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000000945 filler Substances 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 239000000047 product Substances 0.000 claims description 14
- 239000003085 diluting agent Substances 0.000 claims description 11
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 238000006482 condensation reaction Methods 0.000 claims description 9
- 238000005966 aza-Michael addition reaction Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 4
- 238000005260 corrosion Methods 0.000 claims description 4
- 230000007797 corrosion Effects 0.000 claims description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 230000002194 synthesizing effect Effects 0.000 claims description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 235000006708 antioxidants Nutrition 0.000 claims description 2
- 230000001680 brushing effect Effects 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 238000010422 painting Methods 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 238000007761 roller coating Methods 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- 238000010345 tape casting Methods 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims 2
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 abstract description 24
- 238000001723 curing Methods 0.000 description 120
- 229920000647 polyepoxide Polymers 0.000 description 80
- 239000003822 epoxy resin Substances 0.000 description 79
- -1 tert-butylene Chemical group 0.000 description 59
- 239000003921 oil Substances 0.000 description 58
- 239000007788 liquid Substances 0.000 description 52
- 239000000463 material Substances 0.000 description 43
- 239000000853 adhesive Substances 0.000 description 40
- 230000001070 adhesive effect Effects 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 26
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- 239000004215 Carbon black (E152) Substances 0.000 description 20
- 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 20
- 229930195733 hydrocarbon Natural products 0.000 description 20
- 150000002430 hydrocarbons Chemical class 0.000 description 20
- 125000000466 oxiranyl group Chemical group 0.000 description 20
- 150000001412 amines Chemical class 0.000 description 17
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 16
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 125000002877 alkyl aryl group Chemical group 0.000 description 14
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 14
- 150000004985 diamines Chemical class 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 150000004702 methyl esters Chemical class 0.000 description 12
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 11
- 239000008199 coating composition Substances 0.000 description 11
- 125000004474 heteroalkylene group Chemical group 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 150000001335 aliphatic alkanes Chemical class 0.000 description 10
- 238000010438 heat treatment Methods 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 125000004122 cyclic group Chemical group 0.000 description 9
- 239000000835 fiber Substances 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 229920000768 polyamine Polymers 0.000 description 9
- 150000003335 secondary amines Chemical group 0.000 description 9
- 239000012745 toughening agent Substances 0.000 description 9
- 150000002009 diols Chemical class 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 239000007789 gas Substances 0.000 description 7
- 230000006698 induction Effects 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 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 6
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 6
- 239000009261 D 400 Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 239000010408 film Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000011521 glass Substances 0.000 description 5
- 239000012784 inorganic fiber Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 4
- FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- ZFOZVQLOBQUTQQ-UHFFFAOYSA-N Tributyl citrate Chemical compound CCCCOC(=O)CC(O)(C(=O)OCCCC)CC(=O)OCCCC ZFOZVQLOBQUTQQ-UHFFFAOYSA-N 0.000 description 4
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- 150000005690 diesters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- 239000000314 lubricant Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000004005 microsphere Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 125000002560 nitrile group Chemical group 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 4
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- CYFLXLSBHQBMFT-UHFFFAOYSA-N sulfamoxole Chemical group O1C(C)=C(C)N=C1NS(=O)(=O)C1=CC=C(N)C=C1 CYFLXLSBHQBMFT-UHFFFAOYSA-N 0.000 description 4
- 235000007586 terpenes Nutrition 0.000 description 4
- 125000004149 thio group Chemical group *S* 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 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 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- 229920002873 Polyethylenimine Polymers 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000005670 ethenylalkyl group Chemical group 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910021485 fumed silica Inorganic materials 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011490 mineral wool Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 3
- 229920000962 poly(amidoamine) Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 150000003334 secondary amides Chemical class 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000003466 welding Methods 0.000 description 3
- GJEZBVHHZQAEDB-SYDPRGILSA-N (1s,5r)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC[C@H]2O[C@H]21 GJEZBVHHZQAEDB-SYDPRGILSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 2
- CCEFMUBVSUDRLG-KXUCPTDWSA-N (4R)-limonene 1,2-epoxide Natural products C1[C@H](C(=C)C)CC[C@@]2(C)O[C@H]21 CCEFMUBVSUDRLG-KXUCPTDWSA-N 0.000 description 2
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- GRWFGVWFFZKLTI-IUCAKERBSA-N 1S,5S-(-)-alpha-Pinene Natural products CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 2
- DABQKEQFLJIRHU-UHFFFAOYSA-N 2-Propenoic acid, 2-methyl-, 3,3,5-trimethylcyclohexyl ester Chemical compound CC1CC(OC(=O)C(C)=C)CC(C)(C)C1 DABQKEQFLJIRHU-UHFFFAOYSA-N 0.000 description 2
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 2
- MPGABYXKKCLIRW-UHFFFAOYSA-N 2-decyloxirane Chemical compound CCCCCCCCCCC1CO1 MPGABYXKKCLIRW-UHFFFAOYSA-N 0.000 description 2
- NJWSNNWLBMSXQR-UHFFFAOYSA-N 2-hexyloxirane Chemical compound CCCCCCC1CO1 NJWSNNWLBMSXQR-UHFFFAOYSA-N 0.000 description 2
- AAMHBRRZYSORSH-UHFFFAOYSA-N 2-octyloxirane Chemical compound CCCCCCCCC1CO1 AAMHBRRZYSORSH-UHFFFAOYSA-N 0.000 description 2
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 2
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CCEFMUBVSUDRLG-XNWIYYODSA-N Limonene-1,2-epoxide Chemical compound C1[C@H](C(=C)C)CCC2(C)OC21 CCEFMUBVSUDRLG-XNWIYYODSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920006231 aramid fiber Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- ROPXFXOUUANXRR-YPKPFQOOSA-N bis(2-ethylhexyl) (z)-but-2-enedioate Chemical compound CCCCC(CC)COC(=O)\C=C/C(=O)OCC(CC)CCCC ROPXFXOUUANXRR-YPKPFQOOSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229960002713 calcium chloride Drugs 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 2
- 235000012241 calcium silicate Nutrition 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 229940072282 cardura Drugs 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- JBSLOWBPDRZSMB-BQYQJAHWSA-N dibutyl (e)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C\C(=O)OCCCC JBSLOWBPDRZSMB-BQYQJAHWSA-N 0.000 description 2
- 229940090926 diethylhexyl maleate Drugs 0.000 description 2
- RUZYUOTYCVRMRZ-UHFFFAOYSA-N doxazosin Chemical compound C1OC2=CC=CC=C2OC1C(=O)N(CC1)CCN1C1=NC(N)=C(C=C(C(OC)=C2)OC)C2=N1 RUZYUOTYCVRMRZ-UHFFFAOYSA-N 0.000 description 2
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 2
- 238000004836 empirical method Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 238000013007 heat curing Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- UHUUYVZLXJHWDV-UHFFFAOYSA-N trimethyl(methylsilyloxy)silane Chemical compound C[SiH2]O[Si](C)(C)C UHUUYVZLXJHWDV-UHFFFAOYSA-N 0.000 description 1
- RXPQRKFMDQNODS-UHFFFAOYSA-N tripropyl phosphate Chemical compound CCCOP(=O)(OCCC)OCCC RXPQRKFMDQNODS-UHFFFAOYSA-N 0.000 description 1
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- NQFUSWIGRKFAHK-KEMUHUQJSA-N α-pinene-oxide Chemical compound CC12OC1C[C@H]1C(C)(C)[C@@H]2C1 NQFUSWIGRKFAHK-KEMUHUQJSA-N 0.000 description 1
Classifications
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
- C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
-
- 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
- C08G59/54—Amino amides>
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33303—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group
- C08G65/33306—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing amino group acyclic
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
-
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/028—Polyamidoamines
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyethers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11157025.5A EP2495271B1 (en) | 2011-03-04 | 2011-03-04 | Polyether hybrid epoxy curatives |
| EP11157025.5 | 2011-03-04 | ||
| PCT/US2012/023763 WO2012121822A1 (en) | 2011-03-04 | 2012-02-03 | Polyether hybrid epoxy curatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2828693A1 CA2828693A1 (en) | 2012-09-13 |
| CA2828693C true CA2828693C (en) | 2018-02-13 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2828693A Active CA2828693C (en) | 2011-03-04 | 2012-02-03 | Polyether hybrid epoxy curatives |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US9228055B2 (enExample) |
| EP (1) | EP2495271B1 (enExample) |
| JP (1) | JP5889341B2 (enExample) |
| KR (1) | KR20140022817A (enExample) |
| CN (1) | CN103391955B (enExample) |
| AR (1) | AR085520A1 (enExample) |
| AU (1) | AU2012226303B2 (enExample) |
| BR (1) | BR112013022099A2 (enExample) |
| CA (1) | CA2828693C (enExample) |
| MX (1) | MX343828B (enExample) |
| MY (1) | MY175169A (enExample) |
| RU (1) | RU2564664C2 (enExample) |
| WO (1) | WO2012121822A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2497857A1 (de) * | 2011-03-05 | 2012-09-12 | Huntsman Textile Effects (Germany) GmbH | Textile Flächengebilde mit reduzierter Geruchsentwicklung |
| ES2673735T3 (es) | 2013-06-28 | 2018-06-25 | 3M Innovative Properties Company | Uso de composiciones adhesivas basadas en epóxido para rellenar huecos |
| US10203399B2 (en) | 2013-11-12 | 2019-02-12 | Big Sky Financial Corporation | Methods and apparatus for array based LiDAR systems with reduced interference |
| EP3237485A1 (en) | 2014-12-24 | 2017-11-01 | Dow Global Technologies LLC | Rapid-set epoxy resin systems and process of coating pipelines using the epoxy resin system |
| ES2538180B2 (es) * | 2015-04-17 | 2015-11-06 | Universitat Politècnica De Catalunya | Composición para el entrecruzamiento de una amina con un compuesto vinílico alfa,beta-conjugado a un grupo carbonilo de éster y posterior polimerización del compuesto vinílico y procedimientos correspondientes |
| JP2018527733A (ja) * | 2015-08-28 | 2018-09-20 | メルク パテント ゲーエムベーハー | エポキシ基含有溶媒を含む有機機能性材料の調合物 |
| EP3239207B1 (en) | 2016-04-27 | 2021-07-28 | 3M Innovative Properties Company | Curable epoxy compositions |
| EP3275914B1 (en) | 2016-07-29 | 2022-05-11 | 3M Innovative Properties Company | Flame retardant adhesive composition |
| WO2018063095A1 (en) * | 2016-09-29 | 2018-04-05 | Nipsea Technologies Pte Ltd | Crosslinking agent for polymer emulsions |
| EP3375801B1 (en) | 2017-03-16 | 2020-09-30 | 3M Innovative Properties Company | Epoxy casting resin formulation |
| EP3385297A1 (en) | 2017-04-04 | 2018-10-10 | 3M Innovative Properties Company | Epoxy-silicone hybrid sealant composition with low shrinkage and lower postcuring properties with chemical resistance for aerospace applications |
| DE112018005226T5 (de) * | 2017-10-06 | 2020-06-18 | 3M Innovative Properties Company | Härtbare zusammensetzungen, gegenstände daraus und verfahren zu deren herstellung und verwendung |
| EP3489271B1 (en) | 2017-11-22 | 2020-05-27 | 3M Innovative Properties Company | Thermal cycling resistant low density composition |
| US20210122952A1 (en) * | 2018-02-12 | 2021-04-29 | 3M Innovative Properties Company | Curable compositions, articles therefrom, and methods of making and using same |
| CN108570316B (zh) * | 2018-05-30 | 2019-11-08 | 山东大学 | 聚醚胺代替无机碱的asp三元复合驱油剂及其制备方法 |
| CN109575863B (zh) * | 2018-12-11 | 2020-06-26 | 江苏凯伦建材股份有限公司 | 一种粘贴pvc及处理混凝土伸缩缝用的环氧砂浆及其制备方法和应用 |
| KR102155006B1 (ko) * | 2018-12-12 | 2020-09-11 | 한국화학연구원 | 자동차용 이액형 접착제 조성물, 이의 경화물 및 자동차 소재 접착방법 |
| RU2717938C1 (ru) * | 2019-02-25 | 2020-03-27 | 3М Инновейтив Пропертиз Компани | Защитные эпоксидные композиции |
| CN116601236B (zh) * | 2020-09-14 | 2025-08-05 | 株式会社Adeka | 环氧树脂用固化剂组合物、环氧树脂组合物以及涂料 |
| KR102376268B1 (ko) * | 2021-06-01 | 2022-03-18 | 국도화학 주식회사 | 저점도 및 속경화 특성을 갖는 신규한 화합물, 이를 포함하는 경화제 조성물, 이를 포함하는 코팅 조성물 및 이를 포함하는 제조 물품 |
| DE102024106722A1 (de) | 2024-03-08 | 2025-09-11 | Delo Industrie Klebstoffe Gmbh & Co. Kgaa | Härtbare Masse, Verfahren zum Fügen, Beschichten oder Vergießen von Substraten und Verwendung der Masse |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7713455A (nl) | 1977-12-06 | 1979-06-08 | Stamicarbon | Werkwijze voor het in situ winnen van kool. |
| US4240804A (en) * | 1978-01-24 | 1980-12-23 | Sherex Chemical Company, Inc. | Alkyl acrylate adducts of polyamines, ether amines and ether polyamines |
| US4507466A (en) * | 1983-01-07 | 1985-03-26 | The Dow Chemical Corporation | Dense star polymers having core, core branches, terminal groups |
| EP0301716A3 (en) | 1987-07-27 | 1991-01-30 | Texaco Development Corporation | Polyamidopolyamines |
| DE3901279A1 (de) | 1989-01-18 | 1990-07-19 | Hoechst Ag | Verwendung von polyamidoaminen als haerter fuer epoxidharze und diese enthaltende haertbare mischungen |
| US5210195A (en) * | 1991-11-08 | 1993-05-11 | Texaco Chemical Co. | Bis(2,2',6,6'-tetramethyl-4-aminoethyleneamidopiperidyl) polyoxyalkylene |
| IT1254898B (it) * | 1992-04-21 | 1995-10-11 | Gianfranco Palumbo | Idrogeli di tipo polietereammidoamminico come materiali eparinizzabili |
| DE4240110A1 (de) * | 1992-11-28 | 1994-06-01 | Basf Ag | Kondensationsprodukte von Polyalkylenpolyaminen, Verfahren zu ihrer Herstellung und ihre Verwendung bei der Herstellung von Papier |
| JP3099672B2 (ja) * | 1995-03-31 | 2000-10-16 | 東洋インキ製造株式会社 | 星型または櫛状枝分かれ脂肪族ポリアミノ系化合物の製造方法および硬化性樹脂組成物 |
| GB2332202A (en) | 1997-12-09 | 1999-06-16 | Courtaulds Coatings | Curable epoxy resin compositions |
| GB9824423D0 (en) | 1998-11-06 | 1999-01-06 | Wood Limited E | Coating composition |
| US6632872B1 (en) | 2000-09-19 | 2003-10-14 | 3M Innovative Properties Company | Adhesive compositions including self-assembling molecules, adhesives, articles, and methods |
| JP2004027058A (ja) * | 2002-06-26 | 2004-01-29 | Fuji Photo Film Co Ltd | デンドリマー及びその製造方法 |
| JP4248207B2 (ja) * | 2002-08-29 | 2009-04-02 | 川研ファインケミカル株式会社 | 分散剤 |
| JP4321101B2 (ja) | 2002-12-26 | 2009-08-26 | 三菱瓦斯化学株式会社 | 変性鎖状脂肪族ポリアミン |
| US8168713B2 (en) * | 2005-05-12 | 2012-05-01 | Lubrizol Limited | Dispersants and compositions thereof |
| US20080146381A1 (en) * | 2006-12-18 | 2008-06-19 | Kondos Constantine A | Golf balls comprising (meth)acrylated amine curatives |
-
2011
- 2011-03-04 EP EP11157025.5A patent/EP2495271B1/en not_active Not-in-force
-
2012
- 2012-02-03 WO PCT/US2012/023763 patent/WO2012121822A1/en not_active Ceased
- 2012-02-03 CN CN201280010776.0A patent/CN103391955B/zh not_active Expired - Fee Related
- 2012-02-03 AU AU2012226303A patent/AU2012226303B2/en not_active Ceased
- 2012-02-03 CA CA2828693A patent/CA2828693C/en active Active
- 2012-02-03 KR KR1020137025515A patent/KR20140022817A/ko not_active Abandoned
- 2012-02-03 MY MYPI2013003114A patent/MY175169A/en unknown
- 2012-02-03 BR BR112013022099A patent/BR112013022099A2/pt not_active IP Right Cessation
- 2012-02-03 RU RU2013138308/04A patent/RU2564664C2/ru not_active IP Right Cessation
- 2012-02-03 MX MX2013009822A patent/MX343828B/es active IP Right Grant
- 2012-02-03 JP JP2013556635A patent/JP5889341B2/ja not_active Expired - Fee Related
- 2012-02-03 US US14/002,457 patent/US9228055B2/en not_active Expired - Fee Related
- 2012-03-01 AR ARP120100663A patent/AR085520A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US20130333840A1 (en) | 2013-12-19 |
| KR20140022817A (ko) | 2014-02-25 |
| US9228055B2 (en) | 2016-01-05 |
| JP2014506953A (ja) | 2014-03-20 |
| CN103391955A (zh) | 2013-11-13 |
| EP2495271B1 (en) | 2014-04-23 |
| MX2013009822A (es) | 2013-10-03 |
| CN103391955B (zh) | 2015-11-25 |
| AR085520A1 (es) | 2013-10-09 |
| RU2564664C2 (ru) | 2015-10-10 |
| AU2012226303B2 (en) | 2014-10-09 |
| AU2012226303A1 (en) | 2013-09-19 |
| BR112013022099A2 (pt) | 2016-12-06 |
| MY175169A (en) | 2020-06-12 |
| JP5889341B2 (ja) | 2016-03-22 |
| EP2495271A1 (en) | 2012-09-05 |
| CA2828693A1 (en) | 2012-09-13 |
| MX343828B (es) | 2016-11-24 |
| RU2013138308A (ru) | 2015-04-10 |
| WO2012121822A1 (en) | 2012-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20170127 |