DK2571917T3 - Semicarbazoner som acceleratorer til at hærde epoxyharpikser - Google Patents
Semicarbazoner som acceleratorer til at hærde epoxyharpikser Download PDFInfo
- Publication number
- DK2571917T3 DK2571917T3 DK11721758.8T DK11721758T DK2571917T3 DK 2571917 T3 DK2571917 T3 DK 2571917T3 DK 11721758 T DK11721758 T DK 11721758T DK 2571917 T3 DK2571917 T3 DK 2571917T3
- Authority
- DK
- Denmark
- Prior art keywords
- functional group
- alkylaryl
- branched
- cycloalkyl
- epoxy resin
- Prior art date
Links
- 239000003822 epoxy resin Substances 0.000 title claims description 49
- 229920000647 polyepoxide Polymers 0.000 title claims description 49
- 150000007659 semicarbazones Chemical class 0.000 title claims description 46
- 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 title description 17
- 125000000524 functional group Chemical group 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 55
- 239000003795 chemical substances by application Substances 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 19
- -1 R 2 = H Chemical group 0.000 claims description 17
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 16
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 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 claims description 10
- 150000001412 amines Chemical group 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 7
- 229940123208 Biguanide Drugs 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 6
- 235000013824 polyphenols Nutrition 0.000 claims description 6
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 150000004283 biguanides Chemical class 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 150000002357 guanidines Chemical class 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 claims description 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 claims description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 2
- 150000001448 anilines Chemical class 0.000 claims description 2
- 229930003836 cresol Natural products 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 239000004848 polyfunctional curative Substances 0.000 claims 4
- 239000004721 Polyphenylene oxide Substances 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- ZWLIYXJBOIDXLL-UHFFFAOYSA-N decanedihydrazide Chemical class NNC(=O)CCCCCCCCC(=O)NN ZWLIYXJBOIDXLL-UHFFFAOYSA-N 0.000 claims 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical class C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 claims 1
- 238000001723 curing Methods 0.000 description 59
- 229920005989 resin Polymers 0.000 description 20
- 239000011347 resin Substances 0.000 description 20
- 125000000217 alkyl group Chemical group 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 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 5
- 239000004593 Epoxy Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 150000003349 semicarbazides Chemical class 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- MYLMZXNDVMFRBH-UHFFFAOYSA-N 3-amino-1,1-diethylurea Chemical compound CCN(CC)C(=O)NN MYLMZXNDVMFRBH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- FCFXPDZISVZNJB-UHFFFAOYSA-N 3-(cyclopentylideneamino)-1,1-dimethylurea Chemical compound CN(C)C(=O)NN=C1CCCC1 FCFXPDZISVZNJB-UHFFFAOYSA-N 0.000 description 3
- PGLFGNJUOPLFLV-UHFFFAOYSA-N 3-amino-1,1-dimethylurea Chemical compound CN(C)C(=O)NN PGLFGNJUOPLFLV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- PAPCZTWPINXHDN-UHFFFAOYSA-N 1,1-dimethyl-3-(1-phenylethylideneamino)urea Chemical compound CN(C)C(=O)NN=C(C)C1=CC=CC=C1 PAPCZTWPINXHDN-UHFFFAOYSA-N 0.000 description 2
- HGUVLEFZQUHLND-UHFFFAOYSA-N 1,1-dimethyl-3-(4-methylpentan-2-ylideneamino)urea Chemical compound CC(C)CC(C)=NNC(=O)N(C)C HGUVLEFZQUHLND-UHFFFAOYSA-N 0.000 description 2
- VUIMBZIZZFSQEE-UHFFFAOYSA-N 1-(1h-indol-3-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CNC2=C1 VUIMBZIZZFSQEE-UHFFFAOYSA-N 0.000 description 2
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- UIBBSRGDMJYFAK-UHFFFAOYSA-N 3-(butan-2-ylideneamino)-1,1-dimethylurea Chemical compound CCC(C)=NNC(=O)N(C)C UIBBSRGDMJYFAK-UHFFFAOYSA-N 0.000 description 2
- WRACXYFTJDBUCC-UHFFFAOYSA-N 3-(cyclohexylideneamino)-1,1-dimethylurea Chemical compound CN(C)C(=O)NN=C1CCCCC1 WRACXYFTJDBUCC-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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000001994 activation Methods 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 229940024874 benzophenone Drugs 0.000 description 2
- 238000005266 casting Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PJRHFTYXYCVOSJ-UHFFFAOYSA-N cyclopropyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CC1 PJRHFTYXYCVOSJ-UHFFFAOYSA-N 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical compound C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 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
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000007725 thermal activation Methods 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
- JLNXKNOBVAFFFT-UHFFFAOYSA-N 1,1-diethyl-3-(1-phenylethylideneamino)urea Chemical compound CCN(CC)C(=O)NN=C(C)C1=CC=CC=C1 JLNXKNOBVAFFFT-UHFFFAOYSA-N 0.000 description 1
- PVWJZBUMBQDHEJ-UHFFFAOYSA-N 1,1-diethyl-3-(propan-2-ylideneamino)urea Chemical compound CCN(CC)C(=O)NN=C(C)C PVWJZBUMBQDHEJ-UHFFFAOYSA-N 0.000 description 1
- YZRWCYUQZHRZMD-UHFFFAOYSA-N 1,1-dimethyl-3-(propan-2-ylideneamino)urea Chemical compound CN(C)C(=O)NN=C(C)C YZRWCYUQZHRZMD-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- QTAKWZOXNRFSJQ-UHFFFAOYSA-N 3-(benzhydrylideneamino)-1,1-dimethylurea Chemical compound C=1C=CC=CC=1C(=NNC(=O)N(C)C)C1=CC=CC=C1 QTAKWZOXNRFSJQ-UHFFFAOYSA-N 0.000 description 1
- GMVWXZPAXSIJGS-UHFFFAOYSA-N 3-(cyclopentylideneamino)-1,1-diethylurea Chemical compound CCN(CC)C(=O)NN=C1CCCC1 GMVWXZPAXSIJGS-UHFFFAOYSA-N 0.000 description 1
- XHJQWVCYORHJBO-UHFFFAOYSA-N 3-(dicyclopropylmethylideneamino)-1,1-dimethylurea Chemical compound C1CC1C(=NNC(=O)N(C)C)C1CC1 XHJQWVCYORHJBO-UHFFFAOYSA-N 0.000 description 1
- FSVYIXFTGRWWDV-UHFFFAOYSA-N 3-[[cyclopropyl(phenyl)methylidene]amino]-1,1-dimethylurea Chemical compound C=1C=CC=CC=1C(=NNC(=O)N(C)C)C1CC1 FSVYIXFTGRWWDV-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005494 Chlorotoluron Substances 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005533 Fluometuron Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BFDWWMRWLXGJNX-UHFFFAOYSA-N N-[(4-ethylphenyl)diazenyl]-N-methylacetamide Chemical compound CCC1=CC=C(N=NN(C)C(C)=O)C=C1 BFDWWMRWLXGJNX-UHFFFAOYSA-N 0.000 description 1
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- 230000001133 acceleration Effects 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
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- 229910052801 chlorine Inorganic materials 0.000 description 1
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- BJFGVYCULWBXKF-UHFFFAOYSA-M chlormerodrin Chemical compound Cl[Hg]CC(OC)CNC(N)=O BJFGVYCULWBXKF-UHFFFAOYSA-M 0.000 description 1
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- 238000000576 coating method Methods 0.000 description 1
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- 150000002148 esters Chemical class 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
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- RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 238000013467 fragmentation Methods 0.000 description 1
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- 230000006870 function Effects 0.000 description 1
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- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000007620 mathematical function Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- UUIRQFMZIGGUJL-UHFFFAOYSA-N n'-hydroxy-4-piperidin-1-ylbutanimidamide Chemical compound ON=C(N)CCCN1CCCCC1 UUIRQFMZIGGUJL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- GCSHUYKULREZSJ-UHFFFAOYSA-N phenyl(pyridin-2-yl)methanone Chemical compound C=1C=CC=NC=1C(=O)C1=CC=CC=C1 GCSHUYKULREZSJ-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Claims (9)
1. Anvendelse af mindst en semicarbazon med den almene formel (I),
formula (I) hvor R1 = en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R2 = H, en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R3, R4 = samtidigt eller af hinanden, H, en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, alkylaryl-funktionel gruppe, aryl-funktionel gruppe, heteroaryl-funktionel gruppe eller CN; eller R1 = en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R2 = H, en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R3 og R4 = alkylen med -(CH2)n- og 2 < n < 11, som en hærdningsaccelerator til at hærde epoxyharpikssammensætninger ved hjælp af varmeaktiverbar hærder.
2. Anvendelse ifølge krav 1, kendetegnet ved, at den varmeaktiverbare hærder er valgt fra gruppen bestående af aminer, amider, guanidiner, biguanider, carboxylsyreanhydrider eller polyphenoler.
3. Anvendelse ifølge enten krav 1 eller krav 2, kendetegnet ved, at dicyandi-amid anvendes som den varmeaktiverbar hærder.
4. Anvendelse ifølge mindst et af de foregående krav 1 til 3, kendetegnet ved, at semicarbazon eller blandinger af semicarbazoner er/anvendes i en mængde på fra 0,1 til 15 vægt-%, baseret på epoxyharpikssammensætningen.
5. Anvendelse ifølge mindst et af kravene 1 til 4, kendetegnet ved, at semicarbazon eller blandinger af semicarbazoner er/anvendes i et forhold på fra 0,1 til 15 dele, baseret på 100 dele epoxyharpiks.
6. Epoxyharpikssammensætning, der omfatter a) en epoxyharpiks med mindst en reaktiv epoxygruppe, b) mindst en varmeaktiverbar hærder, c) mindst en semicarbazon med den almene formel (I) som en hærdningsaccelerator
formula (I) hvor R1 = en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R2 = H, en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R3, R4 = samtidigt eller uafhængigt af hinanden, H, en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, alkylaryl-funktionel gruppe, aryl-funktionel gruppe, heteroaryl-funktionel gruppe eller CN; eller R1 = en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R2 = H, en forgrenet eller lineær alkyl-funktionel gruppe, cycloalkyl-funktionel gruppe, aryl-funktionel gruppe eller alkylaryl-funktionel gruppe, R3 og R4 = alkylen med -(CH2)n- og 2 < n < 11.
7. Epoxyharpikssammensætning ifølge krav 6, kendetegnet ved, at R1 = methyl, ethyl, benzyl eller phenyl, R2 = H, methyl, ethyl, benzyl eller phenyl, R3, R4 = samtidigt eller uafhængigt af hinanden, H, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, benzyl eller phenyl, eller R1 = methyl, ethyl, benzyl eller phenyl, R2 = H, methyl, ethyl, benzyl eller phenyl, R3 og R4 = alkylen med -(CH2)n- og 2 < n < 6.
8. Epoxyharpikssammensætning ifølge krav 7 eller krav 8, kendetegnet ved, at epoxyharpiksen er udvalgt fra gruppen bestående af glycidyl-polyether af 2,2-bis(4-hydroxyphenyl)-propan (bisphenol A), derivatet deraf, der er substitueret med brom (tetrabrombisphenol A), glycidyl-polyether af 2,2-bis(4-hydroxy-phe-nyl)-methan (bisphenol F) og glycidyl-polyether af novolakharpikser og anilin eller substituerede aniliner, fortrinsvis P-aminophenol eller 4,4'-diamino-diphenyl-methan.
9. Epoxyharpikssammensætning ifølge ethvert af kravene 6 til 8, kendetegnet ved, at biguanider, fortrinsvis ortho-tolylbiguanid (OTB), methylendianilin (MDA, DDM), para-amino-cyclohexyl-metan (PACM), 3,3'- eller 4,4'-diamino-diphenyl-sulfon (DDS), polyetheraminer, dicyandiamid (DCD), adipinsyre- eller sebacin-syre-dihydrazider, pyromellitsyre, trimellitsyre- eller phthalsyreanhydrider, phenol-novolakker eller cresol-novolakker eller blandinger deraf, er indeholdt som varmeaktiverbar hærder.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102010020882A DE102010020882A1 (de) | 2010-05-18 | 2010-05-18 | Semicarbazone zur Härtung von Epoxidharzen |
| PCT/EP2011/058042 WO2011144659A1 (de) | 2010-05-18 | 2011-05-18 | Semicarbazone als beschleuniger zur härtung von epoxidharzen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DK2571917T3 true DK2571917T3 (da) | 2017-03-20 |
Family
ID=44320293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK11721758.8T DK2571917T3 (da) | 2010-05-18 | 2011-05-18 | Semicarbazoner som acceleratorer til at hærde epoxyharpikser |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9403976B2 (da) |
| EP (1) | EP2571917B1 (da) |
| CN (1) | CN102906147B (da) |
| DE (1) | DE102010020882A1 (da) |
| DK (1) | DK2571917T3 (da) |
| PL (1) | PL2571917T3 (da) |
| WO (1) | WO2011144659A1 (da) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102010020882A1 (de) | 2010-05-18 | 2011-11-24 | Alzchem Trostberg Gmbh | Semicarbazone zur Härtung von Epoxidharzen |
| BR112013013450B1 (pt) | 2011-02-23 | 2020-05-05 | Alzchem Ag | Endurecedores para resinas epóxido, composições compreendendo o mesmo e seususos |
| DE102011118501A1 (de) | 2011-11-15 | 2013-05-16 | Alzchem Ag | Alkyl- oder Dialkyl-Semicarbazone als Härter für Epoxidharze |
| DE102011118760A1 (de) | 2011-11-15 | 2013-05-16 | Alzchem Ag | Verwendung von N,N'(-Dimethyl)-Uronen sowie Verfahren zur Härtung von Epoxidharz-Zusammensetzungen |
| DE102012015315A1 (de) * | 2012-08-02 | 2014-05-15 | Alzchem Ag | Flüssige Härter zur Härtung von Epoxidharzen (I) |
| EP2880071B1 (de) * | 2012-08-02 | 2016-09-07 | AlzChem AG | Flüssige härter zur härtung von epoxidharzen (i) |
| DE102012015316A1 (de) * | 2012-08-02 | 2014-05-15 | Alzchem Ag | Flüssige Härter zur Härtung von Epoxidharzen (II) |
| WO2015113931A1 (de) * | 2014-01-29 | 2015-08-06 | Alzchem Ag | Flüssige härterzusammensetzung zur härtung von polymerharzen (ii) |
| DE102014226834A1 (de) | 2014-12-22 | 2016-06-23 | Henkel Ag & Co. Kgaa | Verwendung eines Thiolester als Härter für Epoxid-Klebstoffe |
| CN105237742A (zh) * | 2015-11-14 | 2016-01-13 | 华玉叶 | 一种高粘度固化剂组合物 |
| CN105218787A (zh) * | 2015-11-14 | 2016-01-06 | 华玉叶 | 一种高粘度固化剂组合物 |
| CN105237744A (zh) * | 2015-11-14 | 2016-01-13 | 华玉叶 | 一种高粘度固化剂组合物 |
| CN105218786A (zh) * | 2015-11-14 | 2016-01-06 | 华玉叶 | 一种高粘度固化剂组合物 |
| US11242430B2 (en) * | 2019-10-17 | 2022-02-08 | Ppg Industries Ohio, Inc. | Crosslinking compositions and coatings formed therefrom |
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| DE102010020882A1 (de) | 2010-05-18 | 2011-11-24 | Alzchem Trostberg Gmbh | Semicarbazone zur Härtung von Epoxidharzen |
| DE102011118501A1 (de) | 2011-11-15 | 2013-05-16 | Alzchem Ag | Alkyl- oder Dialkyl-Semicarbazone als Härter für Epoxidharze |
| DE102011118760A1 (de) | 2011-11-15 | 2013-05-16 | Alzchem Ag | Verwendung von N,N'(-Dimethyl)-Uronen sowie Verfahren zur Härtung von Epoxidharz-Zusammensetzungen |
-
2010
- 2010-05-18 DE DE102010020882A patent/DE102010020882A1/de not_active Withdrawn
-
2011
- 2011-05-18 DK DK11721758.8T patent/DK2571917T3/da active
- 2011-05-18 US US13/643,119 patent/US9403976B2/en not_active Expired - Fee Related
- 2011-05-18 EP EP11721758.8A patent/EP2571917B1/de active Active
- 2011-05-18 CN CN201180024146.4A patent/CN102906147B/zh not_active Expired - Fee Related
- 2011-05-18 PL PL11721758T patent/PL2571917T3/pl unknown
- 2011-05-18 WO PCT/EP2011/058042 patent/WO2011144659A1/de not_active Ceased
-
2015
- 2015-11-30 US US14/954,560 patent/US20160083575A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20130079488A1 (en) | 2013-03-28 |
| US20160083575A1 (en) | 2016-03-24 |
| CN102906147B (zh) | 2015-04-08 |
| EP2571917B1 (de) | 2016-12-07 |
| US9403976B2 (en) | 2016-08-02 |
| CN102906147A (zh) | 2013-01-30 |
| PL2571917T3 (pl) | 2017-05-31 |
| EP2571917A1 (de) | 2013-03-27 |
| DE102010020882A1 (de) | 2011-11-24 |
| WO2011144659A1 (de) | 2011-11-24 |
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