FI73235C - Blandning, vilken aer haerdbar under inverkan av luftfuktighet. - Google Patents
Blandning, vilken aer haerdbar under inverkan av luftfuktighet. Download PDFInfo
- Publication number
- FI73235C FI73235C FI801720A FI801720A FI73235C FI 73235 C FI73235 C FI 73235C FI 801720 A FI801720 A FI 801720A FI 801720 A FI801720 A FI 801720A FI 73235 C FI73235 C FI 73235C
- Authority
- FI
- Finland
- Prior art keywords
- alkyl group
- carbon atoms
- group
- hexahydropyrimidine
- mixture
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000012948 isocyanate Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 21
- -1 N'-substituted imidazolidine Chemical class 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- DKYBVKMIZODYKL-UHFFFAOYSA-N 1,3-diazinane Chemical compound C1CNCNC1 DKYBVKMIZODYKL-UHFFFAOYSA-N 0.000 claims description 16
- 150000002513 isocyanates Chemical class 0.000 claims description 14
- 239000004848 polyfunctional curative Substances 0.000 claims description 12
- 229920001228 polyisocyanate Polymers 0.000 claims description 12
- 239000005056 polyisocyanate Substances 0.000 claims description 12
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 11
- 229920000647 polyepoxide Polymers 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 229930040373 Paraformaldehyde Natural products 0.000 description 15
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 14
- 229920002866 paraformaldehyde Polymers 0.000 description 14
- 238000007363 ring formation reaction Methods 0.000 description 14
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 150000002461 imidazolidines Chemical class 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 8
- 230000008878 coupling Effects 0.000 description 7
- 238000010168 coupling process Methods 0.000 description 7
- 238000005859 coupling reaction Methods 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000004922 lacquer Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 150000001728 carbonyl compounds Chemical class 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 3
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 238000010926 purge Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- GFOQOXYNTHEFFL-UHFFFAOYSA-N 1,3-dibenzyl-1,3-diazinane Chemical compound C=1C=CC=CC=1CN(C1)CCCN1CC1=CC=CC=C1 GFOQOXYNTHEFFL-UHFFFAOYSA-N 0.000 description 2
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 description 2
- XRDWVJXCKSCRON-UHFFFAOYSA-N 1,3-dibutyl-1,3-diazinane Chemical compound CCCCN1CCCN(CCCC)C1 XRDWVJXCKSCRON-UHFFFAOYSA-N 0.000 description 2
- CSMFFPADQNMRLV-UHFFFAOYSA-N 1,3-didodecyl-1,3-diazinane Chemical compound CCCCCCCCCCCCN1CCCN(CCCCCCCCCCCC)C1 CSMFFPADQNMRLV-UHFFFAOYSA-N 0.000 description 2
- RFLORVZCOADQJY-UHFFFAOYSA-N 1-(3-acetyl-1,3-diazinan-1-yl)ethanone Chemical compound CC(=O)N1CCCN(C(C)=O)C1 RFLORVZCOADQJY-UHFFFAOYSA-N 0.000 description 2
- RELOFIKZGIJATN-UHFFFAOYSA-N 2-imidazolidin-1-ylethanol Chemical compound OCCN1CCNC1 RELOFIKZGIJATN-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- LAGWVZPUXSKERV-UHFFFAOYSA-N cyclohexane;isocyanic acid Chemical compound N=C=O.C1CCCCC1 LAGWVZPUXSKERV-UHFFFAOYSA-N 0.000 description 2
- 125000004386 diacrylate group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 2
- XJRAOMZCVTUHFI-UHFFFAOYSA-N isocyanic acid;methane Chemical compound C.N=C=O.N=C=O XJRAOMZCVTUHFI-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000000565 sealant Substances 0.000 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 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- RXUVWJWQFPJWOV-OWOJBTEDSA-N (e)-1,2-diisocyanatoethene Chemical compound O=C=N\C=C\N=C=O RXUVWJWQFPJWOV-OWOJBTEDSA-N 0.000 description 1
- ATWLRNODAYAMQS-UHFFFAOYSA-N 1,1-dibromopropane Chemical compound CCC(Br)Br ATWLRNODAYAMQS-UHFFFAOYSA-N 0.000 description 1
- AYCUWIWOZKQLMI-UHFFFAOYSA-N 1,2,3,5-tetrachloro-4,6-diisocyanatobenzene Chemical compound ClC1=C(Cl)C(N=C=O)=C(Cl)C(N=C=O)=C1Cl AYCUWIWOZKQLMI-UHFFFAOYSA-N 0.000 description 1
- MTZUIIAIAKMWLI-UHFFFAOYSA-N 1,2-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC=C1N=C=O MTZUIIAIAKMWLI-UHFFFAOYSA-N 0.000 description 1
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- YCKZTKPSXPJYQB-UHFFFAOYSA-N 1,3,5-tribromo-2,4-diisocyanatobenzene Chemical compound BrC1=CC(Br)=C(N=C=O)C(Br)=C1N=C=O YCKZTKPSXPJYQB-UHFFFAOYSA-N 0.000 description 1
- KZAKHJLUHQYIBM-UHFFFAOYSA-N 1,3-dibutyl-2,2-dimethyl-1,3-diazinane Chemical compound CCCCN1CCCN(CCCC)C1(C)C KZAKHJLUHQYIBM-UHFFFAOYSA-N 0.000 description 1
- PUGRJTJYMUABQZ-UHFFFAOYSA-N 1,3-dibutylimidazolidine Chemical compound CCCCN1CCN(CCCC)C1 PUGRJTJYMUABQZ-UHFFFAOYSA-N 0.000 description 1
- KVWRWYHVNAAYHJ-UHFFFAOYSA-N 1,3-dicyclohexylimidazolidine Chemical compound C1CN(C2CCCCC2)CN1C1CCCCC1 KVWRWYHVNAAYHJ-UHFFFAOYSA-N 0.000 description 1
- ZGNPQKNTQZMSLY-UHFFFAOYSA-N 1,3-didodecylimidazolidine Chemical compound CCCCCCCCCCCCN1CCN(CCCCCCCCCCCC)C1 ZGNPQKNTQZMSLY-UHFFFAOYSA-N 0.000 description 1
- SMWUDAKKCDQTPV-UHFFFAOYSA-N 1,3-dimethylimidazolidine Chemical compound CN1CCN(C)C1 SMWUDAKKCDQTPV-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- RQBUVIFBALZGPC-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenyl)benzene Chemical compound C1=CC(N=C=O)=CC=C1C1=CC=C(N=C=O)C=C1 RQBUVIFBALZGPC-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- IPAHMIKXVYEMHP-UHFFFAOYSA-N C1CN(C(N(C1)C2=CC=CC=C2)CCC(=O)O)C3=CC=CC=C3 Chemical compound C1CN(C(N(C1)C2=CC=CC=C2)CCC(=O)O)C3=CC=CC=C3 IPAHMIKXVYEMHP-UHFFFAOYSA-N 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
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- CJFUNHVCACZJQN-UHFFFAOYSA-N N=C=O.N=C=O.C1=CC=C2CC3=CC=CC=C3C2=C1 Chemical compound N=C=O.N=C=O.C1=CC=C2CC3=CC=CC=C3C2=C1 CJFUNHVCACZJQN-UHFFFAOYSA-N 0.000 description 1
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- ITEATYZKOTUJMO-UHFFFAOYSA-N N=C=O.N=C=O.OC(O)=O Chemical class N=C=O.N=C=O.OC(O)=O ITEATYZKOTUJMO-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
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- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
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- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
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- 230000004888 barrier function Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- KTPIWUHKYIJBCR-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohex-4-ene-1,2-dicarboxylate Chemical compound C1C=CCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 KTPIWUHKYIJBCR-UHFFFAOYSA-N 0.000 description 1
- XFUOBHWPTSIEOV-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) cyclohexane-1,2-dicarboxylate Chemical compound C1CCCC(C(=O)OCC2OC2)C1C(=O)OCC1CO1 XFUOBHWPTSIEOV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
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- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- RVRMXANSMFGKHA-UHFFFAOYSA-N n,n'-didodecylpropane-1,3-diamine Chemical compound CCCCCCCCCCCCNCCCNCCCCCCCCCCCC RVRMXANSMFGKHA-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
-
- 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
- C08G18/30—Low-molecular-weight compounds
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3225—Polyamines
- C08G18/3253—Polyamines being in latent form
- C08G18/3256—Reaction products of polyamines with aldehydes or ketones
-
- 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
- C08G18/64—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63
- C08G18/6415—Macromolecular compounds not provided for by groups C08G18/42 - C08G18/63 having 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
- 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
- C08G59/52—Amino carboxylic 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
- 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
- C08G59/62—Alcohols or phenols
- C08G59/64—Amino alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Thermistors And Varistors (AREA)
- Resistance Heating (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2922176 | 1979-05-31 | ||
| DE2922176A DE2922176C3 (de) | 1979-05-31 | 1979-05-31 | Wasserhärtbare Polyisocyanat- oder Polyepoxid-Gemische |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI801720A7 FI801720A7 (fi) | 1980-12-01 |
| FI73235B FI73235B (fi) | 1987-05-29 |
| FI73235C true FI73235C (fi) | 1987-09-10 |
Family
ID=6072166
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801720A FI73235C (fi) | 1979-05-31 | 1980-05-28 | Blandning, vilken aer haerdbar under inverkan av luftfuktighet. |
Country Status (10)
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2922176C3 (de) * | 1979-05-31 | 1995-11-09 | Akzo Gmbh | Wasserhärtbare Polyisocyanat- oder Polyepoxid-Gemische |
| US4427802A (en) | 1981-07-27 | 1984-01-24 | Hexcel Corporation | Heterocyclic multifunctional amine adducts and curable compositions containing the same |
| US4629769A (en) * | 1985-09-30 | 1986-12-16 | Texaco Inc. | 4,4,6-trimethylhexahydropyrimidine as an epoxy curing agent |
| JPS62127360A (ja) * | 1985-11-27 | 1987-06-09 | Kansai Paint Co Ltd | 樹脂被覆用組成物 |
| US5124210A (en) * | 1987-08-28 | 1992-06-23 | Minnesota Mining And Manufacturing Company | Substrate coated with one part moisture curable urethane composition |
| US4839455A (en) * | 1987-08-28 | 1989-06-13 | Minnesota Mining And Manufacturing Company | One part moisture curable urethane composition |
| DE59004478D1 (de) * | 1989-06-13 | 1994-03-17 | Ciba Geigy | Haftvermittler. |
| JP3034371U (ja) * | 1996-05-13 | 1997-02-18 | 博志 山本 | ブロック運搬具 |
| US6573375B2 (en) | 2000-12-20 | 2003-06-03 | Union Carbide Chemicals & Plastics Technology Corporation | Liquid thickener for surfactant systems |
| US10465039B2 (en) | 2015-11-17 | 2019-11-05 | Evonik Degussa Gmbh | Epoxy curing agents, compositions and uses thereof |
| US10556985B2 (en) | 2015-11-17 | 2020-02-11 | Evonik Operations Gmbh | Nitrogen-containing heterocyclic epoxy curing agents, compositions and methods |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3446808A (en) * | 1964-05-25 | 1969-05-27 | Universal Oil Prod Co | Borates of n-hydroxyalkyl-nitrogen-heterocyclic saturated compounds |
| BE756693A (fr) | 1969-09-26 | 1971-03-25 | Ciba Geigy | Composition de resine epoxyde |
| IL34305A (en) | 1970-01-30 | 1975-02-10 | Rohm & Haas | Hydrocurable compositions comprising an oxazolidine and a polyfunctional isocyanate |
| US3941753A (en) * | 1971-04-06 | 1976-03-02 | Schering Aktiengesellschaft | Prepolymers of polyisocyanates with hydroxy-enamines or hydroxy-ketimines |
| DE2259980A1 (de) * | 1972-12-07 | 1974-06-12 | Bayer Ag | Neue o,n- und n,n-acetale, ein verfahren zu ihrer herstellung und ihre verwendung zur herstellung von polyurethanen |
| US3912691A (en) * | 1973-12-14 | 1975-10-14 | Rohm & Haas | Hydrocurable compositions of hydroxy (polyalkylenecarbonyloxy)-alkyleneoxazolidine and an isocyanate |
| US4024117A (en) * | 1973-12-14 | 1977-05-17 | Rohm And Haas Company | Hydrocurable compositions of hydroxy(polyalkylenecarbonyloxy)-alkyleneoxazolidine and an isocyanate |
| DE2718100A1 (de) * | 1977-04-22 | 1978-10-26 | Bayer Ag | Verfahren zur herstellung von polyisocyanat-polyadditionsprodukten |
| DE2739313A1 (de) * | 1977-09-01 | 1979-03-15 | Bayer Ag | Cycloaminale, ein verfahren zu ihrer herstellung, sowie ihre verwendung |
| US4174337A (en) * | 1978-10-10 | 1979-11-13 | Ppg Industries, Inc. | Hydroxy-functional esters of substituted imidazolidinediones and compositions containing same |
| US4228294A (en) * | 1978-10-10 | 1980-10-14 | Ppg Industries, Inc. | Esters of imidazolidinedione-based diepoxides and coating compositions containing same |
| US4221891A (en) * | 1979-05-21 | 1980-09-09 | Ppg Industries, Inc. | Esters of imidazolidinedione-based triepoxides and coating compositions containing same |
| DE2922176C3 (de) * | 1979-05-31 | 1995-11-09 | Akzo Gmbh | Wasserhärtbare Polyisocyanat- oder Polyepoxid-Gemische |
-
1979
- 1979-05-31 DE DE2922176A patent/DE2922176C3/de not_active Expired - Fee Related
-
1980
- 1980-05-22 US US06/152,368 patent/US4289869A/en not_active Expired - Lifetime
- 1980-05-28 DK DK229380A patent/DK229380A/da not_active Application Discontinuation
- 1980-05-28 FI FI801720A patent/FI73235C/fi not_active IP Right Cessation
- 1980-05-28 BR BR8003337A patent/BR8003337A/pt unknown
- 1980-05-28 EP EP80102957A patent/EP0019906B1/de not_active Expired
- 1980-05-29 AR AR281232A patent/AR224160A1/es active
- 1980-05-30 JP JP7158680A patent/JPS56820A/ja active Granted
- 1980-05-30 NO NO801612A patent/NO153399C/no unknown
- 1980-05-30 ES ES491991A patent/ES8102163A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56820A (en) | 1981-01-07 |
| DE2922176C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1989-07-06 |
| DE2922176A1 (de) | 1981-04-02 |
| NO801612L (no) | 1980-12-01 |
| FI801720A7 (fi) | 1980-12-01 |
| EP0019906B1 (de) | 1984-10-17 |
| US4289869A (en) | 1981-09-15 |
| JPS6321690B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-05-09 |
| DK229380A (da) | 1980-12-01 |
| DE2922176C3 (de) | 1995-11-09 |
| NO153399B (no) | 1985-12-02 |
| FI73235B (fi) | 1987-05-29 |
| AR224160A1 (es) | 1981-10-30 |
| ES491991A0 (es) | 1980-12-16 |
| EP0019906A1 (de) | 1980-12-10 |
| NO153399C (no) | 1986-03-12 |
| ES8102163A1 (es) | 1980-12-16 |
| BR8003337A (pt) | 1980-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AKZO NV |