JP6388288B2 - エポキシ樹脂を硬化させるための液状硬化剤(i) - Google Patents
エポキシ樹脂を硬化させるための液状硬化剤(i) Download PDFInfo
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- JP6388288B2 JP6388288B2 JP2015524775A JP2015524775A JP6388288B2 JP 6388288 B2 JP6388288 B2 JP 6388288B2 JP 2015524775 A JP2015524775 A JP 2015524775A JP 2015524775 A JP2015524775 A JP 2015524775A JP 6388288 B2 JP6388288 B2 JP 6388288B2
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- Prior art keywords
- curing agent
- alkyl
- nhc
- liquid curing
- hydrogen
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- 239000003795 chemical substances by application Substances 0.000 title claims description 142
- 239000007788 liquid Substances 0.000 title claims description 110
- 239000003822 epoxy resin Substances 0.000 title claims description 61
- 229920000647 polyepoxide Polymers 0.000 title claims description 61
- -1 Ke tons Chemical class 0.000 claims description 205
- 239000000203 mixture Substances 0.000 claims description 84
- 150000003672 ureas Chemical class 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 239000004034 viscosity adjusting agent Substances 0.000 claims description 39
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000002131 composite material Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 229920005862 polyol Polymers 0.000 claims description 15
- 150000003077 polyols Chemical class 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- 150000007522 mineralic acids Chemical class 0.000 claims description 11
- 150000001299 aldehydes Chemical class 0.000 claims description 10
- 150000002825 nitriles Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methyl urea Chemical compound CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 5
- 239000002657 fibrous material Substances 0.000 claims description 5
- YBBLOADPFWKNGS-UHFFFAOYSA-N 1,1-dimethylurea Chemical compound CN(C)C(N)=O YBBLOADPFWKNGS-UHFFFAOYSA-N 0.000 claims description 4
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 229940057054 1,3-dimethylurea Drugs 0.000 claims description 3
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 3
- 229960004889 salicylic acid Drugs 0.000 claims description 3
- NEVYNAFJLYYHPR-UHFFFAOYSA-N 3-[3-(dimethylcarbamoylamino)-2-methylphenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=CC(NC(=O)N(C)C)=C1C NEVYNAFJLYYHPR-UHFFFAOYSA-N 0.000 claims description 2
- MOAPNXVHLARBNQ-UHFFFAOYSA-N 3-[4-[[4-(dimethylcarbamoylamino)phenyl]methyl]phenyl]-1,1-dimethylurea Chemical compound C1=CC(NC(=O)N(C)C)=CC=C1CC1=CC=C(NC(=O)N(C)C)C=C1 MOAPNXVHLARBNQ-UHFFFAOYSA-N 0.000 claims description 2
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 claims description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims 2
- PLFFHJWXOGYWPR-HEDMGYOXSA-N (4r)-4-[(3r,3as,5ar,5br,7as,11as,11br,13ar,13bs)-5a,5b,8,8,11a,13b-hexamethyl-1,2,3,3a,4,5,6,7,7a,9,10,11,11b,12,13,13a-hexadecahydrocyclopenta[a]chrysen-3-yl]pentan-1-ol Chemical compound C([C@]1(C)[C@H]2CC[C@H]34)CCC(C)(C)[C@@H]1CC[C@@]2(C)[C@]4(C)CC[C@@H]1[C@]3(C)CC[C@@H]1[C@@H](CCCO)C PLFFHJWXOGYWPR-HEDMGYOXSA-N 0.000 claims 1
- 241000023320 Luma <angiosperm> Species 0.000 claims 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 32
- 238000000034 method Methods 0.000 description 32
- 238000002347 injection Methods 0.000 description 25
- 239000007924 injection Substances 0.000 description 25
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 229920000570 polyether Polymers 0.000 description 17
- 239000002952 polymeric resin Substances 0.000 description 16
- 229920003002 synthetic resin Polymers 0.000 description 16
- 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 13
- 150000001298 alcohols Chemical class 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000004721 Polyphenylene oxide Substances 0.000 description 10
- 239000000835 fiber Substances 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 150000008064 anhydrides Chemical class 0.000 description 8
- 150000002170 ethers Chemical class 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- 229920005749 polyurethane resin Polymers 0.000 description 8
- 230000009257 reactivity Effects 0.000 description 8
- 239000011342 resin composition Substances 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000000654 additive Substances 0.000 description 6
- 150000002009 diols Chemical class 0.000 description 6
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000002460 imidazoles Chemical class 0.000 description 5
- 150000002462 imidazolines Chemical class 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 150000001414 amino alcohols Chemical class 0.000 description 4
- 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 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 238000005470 impregnation Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 150000003628 tricarboxylic acids Chemical class 0.000 description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 description 2
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 2
- KDQTUCKOAOGTLT-UHFFFAOYSA-N 3-[3-(dimethylcarbamoylamino)-4-methylphenyl]-1,1-dimethylurea Chemical compound CN(C)C(=O)NC1=CC=C(C)C(NC(=O)N(C)C)=C1 KDQTUCKOAOGTLT-UHFFFAOYSA-N 0.000 description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 description 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004609 Impact Modifier Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical compound OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
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- 239000003607 modifier Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- SJWFXCIHNDVPSH-UHFFFAOYSA-N octan-2-ol Chemical compound CCCCCCC(C)O SJWFXCIHNDVPSH-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000003672 processing method Methods 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- ULPMRIXXHGUZFA-UHFFFAOYSA-N (R)-4-Methyl-3-hexanone Natural products CCC(C)C(=O)CC ULPMRIXXHGUZFA-UHFFFAOYSA-N 0.000 description 1
- NKJOXAZJBOMXID-UHFFFAOYSA-N 1,1'-Oxybisoctane Chemical compound CCCCCCCCOCCCCCCCC NKJOXAZJBOMXID-UHFFFAOYSA-N 0.000 description 1
- IUPSCXDOKZWYRB-UHFFFAOYSA-N 1,2,3$l^{2}-triphosphirene Chemical compound [P]1P=P1 IUPSCXDOKZWYRB-UHFFFAOYSA-N 0.000 description 1
- YAXKTBLXMTYWDQ-UHFFFAOYSA-N 1,2,3-butanetriol Chemical compound CC(O)C(O)CO YAXKTBLXMTYWDQ-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C08G18/82—Post-polymerisation treatment
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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
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
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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
- C08G59/4007—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
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
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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
- C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
- C08G71/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Description
R1、R2は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキルであるか、または一緒になってC3〜C10アルキレン環を形成し;
R3は、水素、C1〜C15アルキル、C3〜C15シクロアルキル、アリール、アリールアルキル、
−NHC(O)NR1R2で置換されたC1〜C15アルキル、
−NHC(O)NR1R2で置換されたC3〜C15シクロアルキル、
−NHC(O)NR1R2で置換されたアリール、または
−NHC(O)NR1R2で置換されたアリールアルキルである]を有している。
を意味してもよい。
R1、R2は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C5シクロアルキル、または一緒になってC3〜C10アルキレン環を形成し;
R4、R4'、R5、R5'、R6、R6'、R7、R7'、R8、R8'は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキル、−NHC(O)NR1R2、または−NHC(O)NR1R2で置換されたC1〜C15アルキルである。
R4、R5、R6、R7、R8は、水素、ハロゲン、C1〜C15アルキル、C3〜C15シクロアルキル、アリール、アリールアルキル、−CF3、−NHC(O)NR1R2、
−NHC(O)NR1R2で置換されたC1〜C15アルキル、
−NHC(O)NRR2で置換されたアリール、または
−NHC(O)NR1R2で置換されたアリールアルキルであり;
R9、R10は、同時にまたは互いに独立して水素、またはC1〜C5アルキルであり;
nは、0〜10の数である。
R11、R22は、同時にまたは互いに独立して水素、−OHまたはC1〜C15アルキルであり;
R12、R14、R16、R18、R20は、同時にまたは互いに独立して水素、−OHまたはC1〜C5アルキルであり;
R13、R15、R17、R19、R21は、同時にまたは互いに独立して水素、−OH、−NH2またはC1〜C5アルキルであり;
ここで、
m、n、o、s、p、q、tは、同時にまたは互いに独立して0〜10、特に0〜5の数であり;ここで、
i)m、s、uは、同時にもしくは互いに独立して1〜10、特に1〜5の数である;および/または
ii)p,t,uは、同時にもしくは互いに独立して1〜10、特に1〜5の数である。
R30は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキル、アリール、アリールアルキルであり;
R32、R34は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキルであるか、または一緒になってC3〜C15アルキレン環を形成し;
R33、R35は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキル、または一緒になってC3〜C15アルキレン環を形成する]を有している。
R30は、水素、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、ヘプチル、オクチル、ノニル、デカニルまたはフェニルであり;
R32、R34は、同時にまたは互いに独立して水素、C1〜C5アルキルまたはフェニルであり;
R33、R35は、同時にまたは互いに独立して水素、C1〜C5アルキルまたはフェニルである。
a)シアナミド1〜50重量部、
b)一般式(I)、(II)および/または(IV)の少なくとも1種の尿素誘導体1〜50重量部、
c)少なくとも1種の粘度調整剤0.01〜50重量部、
d)一般式(VI)のイミダゾリンおよび/または一般式(VII)のイミダゾールのクラスからの少なくとも1種の硬化促進剤0〜10重量部、
e)少なくとも1種の安定剤0〜10重量部
を含んでいる。
a)粘度調整剤および硬化促進剤を有する液状硬化剤
装置:二重壁反応容器500ml、サーモスタット、KPG撹拌器、3枚パドル型金属撹拌器、温度計、粉末漏斗、
実施:前記粉末漏斗を介して、まずシアナミド、種々の尿素(B1、B2、B4)、粘度調整剤(M3)ならびに硬化促進剤(l1〜l6)を前記反応容器に入れる。次に、前記二重壁反応容器に40〜42℃の温水を送り込んで、3枚パドル型金属撹拌器(200rpm)の電源を入れる。ここで、粘度調整剤に応じて、35〜40℃の内部温度にて、20〜40分後に液状硬化剤が製造される。続いて、この液状硬化剤を20〜25℃に冷却して、ガラス容器に詰め替えて、23℃で貯蔵する。
装置:二重壁反応容器500ml、サーモスタット、KPG撹拌器、3枚パドル型金属撹拌器、温度計、粉末漏斗、
実施:前記粉末漏斗を介して、まずシアナミド、種々の尿素(B1、B2、B4)、ならびに粘度調整剤(M1〜M10)を前記反応容器に入れる。次に、前記二重壁反応容器に40〜42℃の温水を送り込んで、3枚型パドル撹拌器(200rpm)の電源を入れる。ここで、粘度調整剤に応じて、35〜40℃の内部温度にて、20〜40分後に液状硬化剤が製造される。 続いて、この液状硬化剤を20〜25℃に冷却して、ガラス容器に詰め替えて、23℃で貯蔵する。
a)本発明によるエポキシ樹脂組成物の組成
使用試験のために、本発明による液状硬化剤を有するエポキシ樹脂組成物を、同一の混合割合(それぞれエポキシ樹脂100重量部、液状硬化剤10重量部)で使用した。
分散容器250mlに、エポキシ樹脂(Epikote828 LVEL)100重量部、および表1〜表3に記載の本発明による硬化剤10重量部を秤量導入して、溶解機で500rpmで2分間混合する。続いて、この混合物を真空で10分間脱気する。
貯蔵容器:ガラスビーカー
真空:真空ポンプ標準(15〜20mbar)。
エポキシ樹脂組成物E2、E20を、加熱可能な貯蔵容器内で混合し、あらかじめ加熱する。導入チューブを、前記貯蔵容器に導入して固定し、導出チューブ(注入試験の構成は表5を参照)を安全バルブを介して真空ポンプに連結し、ポンプの電源を入れる。前記熱板(加熱可能な成形型を模倣するもの)を、注入温度にする。真空をかけて、前記エポキシ樹脂組成物を繊維複合物で吸引する。完全に含浸させた後、導入チューブおよび導出チューブを外して蓋をして、ここで、前記構成全体が、熱板上で完全に硬化して積層体になる。完全な硬化および冷却の後、この積層体を前記構成から取り出す。
Claims (17)
- エポキシ樹脂を硬化させるための液状硬化剤であって、以下
a)シアナミド;
b)一般式(I)
R1、R2は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキル、または一緒になってC3〜C10アルキレン環を形成し;
R3は、水素、C1〜C15アルキル、C3〜C15シクロアルキル、アリール、アリールアルキル、
−NHC(O)NR1R2で置換されたC1〜C15アルキル、
−NHC(O)NR1R2で置換されたC3〜C15シクロアルキル、
−NHC(O)NR1R2で置換されたアリール、または
−NHC(O)NR1R2で置換されたアリールアルキルである]の少なくとも1種の尿素誘導体;
ならびに
c)モノオール、ポリオール、ケトン、アルデヒド、ニトリル、カルボン酸エステルまたはそれらの混合物の群から選択される少なくとも1種の粘度調整剤
を含む前記液状硬化剤。 - シアナミドと、一般式(I)の少なくとも1種の尿素誘導体とを、シアナミド:尿素誘導体または尿素誘導体混合物のモル比1:1〜4:1で含むことを特徴とする、請求項1に記載の液状硬化剤。
- アリール、アリールアルキル、−NHC(O)NR1R2で置換されたアリールまたは−NHC(O)NR1R2で置換されたアリールアルキルであるR3基が、一般式(III)
R4、R5、R6、R7、R8は、水素、C1〜C15アルキル、C3〜C15シクロアルキル、アリール、アリールアルキル、−NHC(O)NR1R2、
−NHC(O)NR1R2で置換されたC1〜C15アルキル、
−NHC(O)NR1R2で置換されたアリール、または
−NHC(O)NR1R2で置換されたアリールアルキルであり;
R9、R10は、同時にまたは互いに独立して水素またはC1〜C5アルキルであり;
nは、0〜10の整数である]の基を表すことを特徴とする、請求項1または2に記載の液状硬化剤。 - 前記尿素誘導体の一般式(I)において、
R1、R2は、同時にまたは互いに独立して水素またはC1〜C15アルキルであり;
R3は、水素、C1〜C15アルキル、C3〜C15シクロアルキル、
−NHC(O)NR1R2で置換されたC1〜C15アルキル、または
−NHC(O)NR1R2で置換されたC3〜C15シクロアルキルであることを特徴とする、請求項1または2に記載の液状硬化剤。 - 一般式(I)で示される尿素誘導体が、1−メチル尿素、1,1−ジメチル尿素、1,3−ジメチル尿素、3−フェニル−1,1−ジメチル尿素、1,1’−(メチレンジ−p−フェニレン)−ビス−(3,3−ジメチル尿素)、1,1’−(2−メチル−m−フェニレン)−ビス−(3,3−ジメチル尿素)および/または1,1’−(4−メチル−m−フェニレン)−ビス−(3,3−ジメチル尿素)の群から選択されることを特徴とする、請求項1または2に記載の液状硬化剤。
- 前記粘度調整剤は、それ自身が少なくとも100℃の沸点を有することを特徴とする、請求項1から5までのいずれか1項に記載の液状硬化剤。
- 前記粘度調整剤が、一般式(V)
R11、R22は、同時にまたは互いに独立して水素、−OHまたはC1〜C10アルキルであり;
R12、R14、R16、R18、R20は、同時にまたは互いに独立して水素、−OHまたはC1〜C5アルキルであり;
R13、R15、R17、R19、R21は、同時にまたは互いに独立して、水素、−OH、−NH2またはC1〜C5アルキルであり(ただし、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 およびR 22 の全てが同時にアルキルではなく、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 およびR 22 の全てが同時に水素ではなく、且つ、R 11 、R 12 、R 13 、R 14 、R 15 、R 16 、R 17 、R 18 、R 19 、R 20 、R 21 およびR 22 の少なくとも1つは−OHである);
ここで、
m、n、o、s、p、q、tは、同時にまたは互いに独立して0〜10の整数であり、ここで、
i)m、s、uは、同時にもしくは互いに独立して1〜10の整数である、および/または
ii)p、t、uは、同時にもしくは互いに独立して1〜10の整数である]
で示される、モノオール、ポリオールまたはそれらの混合物の群から選択されることを特徴とする、請求項1から6までのいずれか1項に記載の液状硬化剤。 - e)無機または有機の酸の群から選択される安定剤をさらに含むことを特徴とする、請求項1から7までのいずれか1項に記載の液状硬化剤。
- 前記安定剤e)が、サリチル酸、フタル酸、トルエンスルホン酸、硫酸、リン酸、もしくはそれらの無水物、もしくはそれらの混合物の群からの無機または有機の酸であることを特徴とする、請求項8に記載の液状硬化剤。
- シアナミド1重量部に対し、
一般式(I)の少なくとも1種の尿素誘導体1〜50重量部、
少なくとも1種の粘度調整剤0.01〜50重量部、または、
シアナミド50重量部に対し、
一般式(I)の少なくとも1種の尿素誘導体1〜50重量部、
少なくとも1種の粘度調整剤0.01〜50重量部
を含むことを特徴とする、請求項1から7までのいずれか1項に記載の液状硬化剤。 - a)少なくとも1種の硬化性エポキシ樹脂、および
b)請求項1から10までのいずれか1項に記載の少なくとも1種の液状硬化剤
を含むエポキシ樹脂組成物。 - a)繊維材料、
b)少なくとも1種の硬化性エポキシ樹脂、ならびに
c)請求項1から10までのいずれか1項に記載の少なくとも1種の液状硬化剤
を含む複合物材料。 - 請求項1から10までのいずれか1項に記載の液状硬化剤の、エポキシ樹脂に含浸された繊維材料を硬化させるための使用。
- 温度20℃(標準圧)にて液状で存在しており、且つ粘度1Pa・s未満を有することを特徴とする、請求項1から10までのいずれか1項に記載の液状硬化剤。
- 一般式(I)におけるR1およびR2がメチル基を表すことを特徴とする、請求項1から10までのいずれか1項に記載の液状硬化剤。
- 一般式(I)で示される尿素誘導体が、一般式(IV)
R1、R2は、同時にまたは互いに独立して水素、C1〜C15アルキル、C3〜C15シクロアルキル、または一緒になってC3〜C10アルキレン環を形成し、
R4、R5は、水素、C1〜C15アルキル、C3〜C15シクロアルキル、アリール、アリールアルキル、−NHC(O)NR1R2、
−NHC(O)NR1R2で置換されたC1〜C15アルキル、
−NHC(O)NR1R2で置換されたアリール、または
−NHC(O)NR1R2で置換されたアリールアルキルである]
の尿素誘導体であることを特徴とする、請求項1から3までのいずれか1項に記載の液状硬化剤。
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DE201210015316 DE102012015316A1 (de) | 2012-08-02 | 2012-08-02 | Flüssige Härter zur Härtung von Epoxidharzen (II) |
DE102012015315.5 | 2012-08-02 | ||
DE201210015315 DE102012015315A1 (de) | 2012-08-02 | 2012-08-02 | Flüssige Härter zur Härtung von Epoxidharzen (I) |
DE102012015316.3 | 2012-08-02 | ||
PCT/EP2013/066078 WO2014020060A2 (de) | 2012-08-02 | 2013-07-31 | Flüssige härter zur härtung von epoxidharzen (i) |
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CA2816725C (en) | 2011-02-23 | 2018-10-23 | Alzchem Ag | Novel curing agents for epoxy resins |
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