EP0000605B1 - Härtungsmittel für wässerige Epoxydharzdispersionen, deren Herstellung und Verwendung - Google Patents
Härtungsmittel für wässerige Epoxydharzdispersionen, deren Herstellung und Verwendung Download PDFInfo
- Publication number
- EP0000605B1 EP0000605B1 EP78200101A EP78200101A EP0000605B1 EP 0000605 B1 EP0000605 B1 EP 0000605B1 EP 78200101 A EP78200101 A EP 78200101A EP 78200101 A EP78200101 A EP 78200101A EP 0000605 B1 EP0000605 B1 EP 0000605B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- adduct
- weight
- polyamine
- component
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 229920000647 polyepoxide Polymers 0.000 title claims description 72
- 239000003822 epoxy resin Substances 0.000 title claims description 62
- 239000006185 dispersion Substances 0.000 title claims description 39
- 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 claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000004848 polyfunctional curative Substances 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims description 52
- -1 epoxide compound Chemical class 0.000 claims description 42
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 229920000768 polyamine Polymers 0.000 claims description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 229920001281 polyalkylene Polymers 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- 239000007795 chemical reaction product Substances 0.000 claims description 15
- 229920000570 polyether Polymers 0.000 claims description 15
- 229920005862 polyol Polymers 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 14
- 150000003077 polyols Chemical class 0.000 claims description 14
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002118 epoxides Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- 235000013824 polyphenols Nutrition 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000008199 coating composition Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 description 26
- 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 22
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 17
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 15
- IGFHQQFPSIBGKE-UHFFFAOYSA-N 4-nonylphenol Chemical compound CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 12
- 125000003700 epoxy group Chemical group 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 8
- 125000002947 alkylene group Chemical group 0.000 description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 8
- 239000004568 cement Substances 0.000 description 8
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- XPXMKIXDFWLRAA-UHFFFAOYSA-N hydrazinide Chemical compound [NH-]N XPXMKIXDFWLRAA-UHFFFAOYSA-N 0.000 description 5
- 229920000962 poly(amidoamine) Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000004570 mortar (masonry) Substances 0.000 description 4
- 239000011253 protective coating Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 230000000630 rising effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- LLPKQRMDOFYSGZ-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole Chemical compound CC1=CN=C(C)N1 LLPKQRMDOFYSGZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 2
- BTXXTMOWISPQSJ-UHFFFAOYSA-N 4,4,4-trifluorobutan-2-one Chemical compound CC(=O)CC(F)(F)F BTXXTMOWISPQSJ-UHFFFAOYSA-N 0.000 description 2
- BQACOLQNOUYJCE-FYZZASKESA-N Abietic acid Natural products CC(C)C1=CC2=CC[C@]3(C)[C@](C)(CCC[C@@]3(C)C(=O)O)[C@H]2CC1 BQACOLQNOUYJCE-FYZZASKESA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000006004 Quartz sand Substances 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000010425 asbestos Substances 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229910052895 riebeckite Inorganic materials 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- RZUNIXAGSKNOIB-HSFFGMMNSA-N (1z,3e)-cyclododeca-1,3-diene Chemical compound C1CCCC\C=C/C=C/CCC1 RZUNIXAGSKNOIB-HSFFGMMNSA-N 0.000 description 1
- UJOYFRCOTPUKAK-MRVPVSSYSA-N (R)-3-ammonio-3-phenylpropanoate Chemical compound OC(=O)C[C@@H](N)C1=CC=CC=C1 UJOYFRCOTPUKAK-MRVPVSSYSA-N 0.000 description 1
- IUGDILGOLSSKNE-UHFFFAOYSA-N 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane Chemical compound C1=CC(O)=CC=C1C(C(Cl)(Cl)Cl)C1=CC=C(O)C=C1 IUGDILGOLSSKNE-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-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
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical class C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 1
- DNVUITIVPMGLBU-UHFFFAOYSA-N 1,3,5-trithiane 1,1,3,3,5,5-hexaoxide Chemical compound O=S1(=O)CS(=O)(=O)CS(=O)(=O)C1 DNVUITIVPMGLBU-UHFFFAOYSA-N 0.000 description 1
- 229940058015 1,3-butylene glycol Drugs 0.000 description 1
- PRBHEGAFLDMLAL-UHFFFAOYSA-N 1,5-Hexadiene Natural products CC=CCC=C PRBHEGAFLDMLAL-UHFFFAOYSA-N 0.000 description 1
- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
- JPZYXGPCHFZBHO-UHFFFAOYSA-N 1-aminopentadecane Chemical compound CCCCCCCCCCCCCCCN JPZYXGPCHFZBHO-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- WPZJSWWEEJJSIZ-UHFFFAOYSA-N 2,6-dibromo-4-[(3,5-dibromo-4-hydroxyphenyl)methyl]phenol Chemical compound C1=C(Br)C(O)=C(Br)C=C1CC1=CC(Br)=C(O)C(Br)=C1 WPZJSWWEEJJSIZ-UHFFFAOYSA-N 0.000 description 1
- BBBUAWSVILPJLL-UHFFFAOYSA-N 2-(2-ethylhexoxymethyl)oxirane Chemical compound CCCCC(CC)COCC1CO1 BBBUAWSVILPJLL-UHFFFAOYSA-N 0.000 description 1
- WISUILQECWFZCN-UHFFFAOYSA-N 2-(oxiran-2-ylmethylsulfanylmethyl)oxirane Chemical compound C1OC1CSCC1CO1 WISUILQECWFZCN-UHFFFAOYSA-N 0.000 description 1
- XBQRPFBBTWXIFI-UHFFFAOYSA-N 2-chloro-4-[2-(3-chloro-4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C=1C=C(O)C(Cl)=CC=1C(C)(C)C1=CC=C(O)C(Cl)=C1 XBQRPFBBTWXIFI-UHFFFAOYSA-N 0.000 description 1
- QHCCOYAKYCWDOJ-UHFFFAOYSA-N 2-ethyl-1h-benzimidazole Chemical compound C1=CC=C2NC(CC)=NC2=C1 QHCCOYAKYCWDOJ-UHFFFAOYSA-N 0.000 description 1
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 1
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical group CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical group CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- VQMPTVQCADWACQ-UHFFFAOYSA-N 3-methylpentan-3-amine Chemical compound CCC(C)(N)CC VQMPTVQCADWACQ-UHFFFAOYSA-N 0.000 description 1
- NOGYFAIHVRCHRE-UHFFFAOYSA-N 4-[(3,5-difluoro-4-hydroxyphenyl)methyl]-2,6-difluorophenol Chemical compound C1=C(F)C(O)=C(F)C=C1CC1=CC(F)=C(O)C(F)=C1 NOGYFAIHVRCHRE-UHFFFAOYSA-N 0.000 description 1
- IJSGQDFHZUWQES-UHFFFAOYSA-N 4-[(4-chlorophenyl)-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(Cl)=CC=1)C1=CC=C(O)C=C1 IJSGQDFHZUWQES-UHFFFAOYSA-N 0.000 description 1
- MIFGCULLADMRTF-UHFFFAOYSA-N 4-[(4-hydroxy-3-methylphenyl)methyl]-2-methylphenol Chemical compound C1=C(O)C(C)=CC(CC=2C=C(C)C(O)=CC=2)=C1 MIFGCULLADMRTF-UHFFFAOYSA-N 0.000 description 1
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 description 1
- RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-UHFFFAOYSA-N 0.000 description 1
- YZYGDZRBLOLVDY-UHFFFAOYSA-N 4-[cyclohexyl-(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1CCCCC1 YZYGDZRBLOLVDY-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- IWYRWIUNAVNFPE-UHFFFAOYSA-N Glycidaldehyde Chemical compound O=CC1CO1 IWYRWIUNAVNFPE-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical group NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical group OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000011280 coal tar Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229930003836 cresol Chemical group 0.000 description 1
- ZOLLIQAKMYWTBR-RYMQXAEESA-N cyclododecatriene Chemical compound C/1C\C=C\CC\C=C/CC\C=C\1 ZOLLIQAKMYWTBR-RYMQXAEESA-N 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004070 electrodeposition Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 150000002193 fatty amides Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Substances O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- SXCBDZAEHILGLM-UHFFFAOYSA-N heptane-1,7-diol Chemical compound OCCCCCCCO SXCBDZAEHILGLM-UHFFFAOYSA-N 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- VXXLEXCQCSPKFI-UHFFFAOYSA-N n-butylcyclohexanamine Chemical compound CCCCNC1CCCCC1 VXXLEXCQCSPKFI-UHFFFAOYSA-N 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000009182 swimming Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- VSRBKQFNFZQRBM-UHFFFAOYSA-N tuaminoheptane Chemical compound CCCCCC(C)N VSRBKQFNFZQRBM-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
- 239000002023 wood 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31525—Next to glass or quartz
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31529—Next to metal
Definitions
- DE-A-1925941 describes epoxy resin hardener emulsions which contain, as hardener component, an aminoamide adduct which is an aminoamide of a fatty acid and an alkylene polyamine and which is the reaction product of the aminoamide with 10-40 percent by weight (based on the weight the highly volatile aminoamide adduct components) is monoepoxide, which consists of an aliphatic monoepoxide with 2-12 C atoms or of a monoepoxide substituted by a phenyl radical.
- an aminoamide adduct which is an aminoamide of a fatty acid and an alkylene polyamine and which is the reaction product of the aminoamide with 10-40 percent by weight (based on the weight the highly volatile aminoamide adduct components) is monoepoxide, which consists of an aliphatic monoepoxide with 2-12 C atoms or of a monoepoxide substituted by a phenyl radical.
- CH-A-487955 describes curable, aqueous dispersions which contain a hardener for the epoxy resin which is liquid at room temperature, the hydrogen being bound directly to the nitrogen in the hardener, which is formed by addition of non-aliphatic epoxide, which is only a terminal 1, Contains 2-epoxy group per molecule, or aliphatic epoxy, which contains on average one or more than one terminal, 1,2-epoxy group per molecule, and a stoichiometric excess of a poly (aminoamide) condensation product, which consists of an alkylene polyamine of the formula wherein the alkylene radical can be the ethylene, propylene, butylene, pentylene or hexylene radical, n is an integer greater than zero, and a copolymer of a conjugated unsaturated fatty acid or an amide-dying acid derivative with an aromatic vinyl compound is available.
- a hardener for the epoxy resin which is liquid at room temperature
- the hydrogen being bound directly to the nitrogen
- aqueous dispersions preferably also contain an accelerator for curing.
- accelerators are compounds which contain at least one tertiary amino nitrogen atom and one phenolic hydroxyl group.
- the dispersions contain orthophosphoric acid or a liquid aliphatic monocarboxylic acid, e.g. B. acetic acid.
- These epoxy hardener dispersions also have insufficient stability and only provide relatively soft and mechanically sensitive protective coatings. Furthermore, the presence of the dissociating acids leads to instability of the dispersion, since the acid anion (A) can react with the epoxy group according to the following scheme and consumes epoxy groups: O
- FR-A-2068390 describes water-dilutable auxiliaries for the emulsification and curing of epoxy resins which consist of reaction products from glycidyl ethers of polyalkylene polyether polyols and polyamines.
- FR-A-2128773 describes a curing agent for epoxy resins in the form of a reaction product of a) at least one diamine, b) a polyfunctional polymer, e.g. B. a butadiene homo- or copolymer and optionally c) a polyepoxide.
- the proportion of amine a) is 20-80%, based on the reaction product from a), b) and c).
- these mixtures are only used in organic solvent systems.
- the polymeric components b) used there are not polyalkylene-polyether-polyols and the amine excess there is significantly higher than in the curing agents according to the invention.
- the adduct is composed of 2 to 4 equivalents of component a1) and 0.2 to 1.5 equivalents of component a2) with 80-20% by weight of component B) and up to 0.5, preferably 0 , 1 to 0.3 equivalents of component C) available.
- A1 is preferably water-insoluble and a2 is water-soluble.
- Another object of the invention is also a method for producing the hardening agents, as described in claims 5 to 7.
- the hydroxyl groups of the polyalkylene polyether polyol are preferably reacted with the epoxy groups at 20 to 200.degree.
- the invention also relates to the use of the curing agents obtained by the abovementioned processes together with polyfunctional epoxy compounds and what water and optionally emulsifiers for the production of curable, optionally film-forming dispersions as coating or coating agents.
- the epoxies of polyunsaturated hydrocarbons (vinylcyclohexene, dicyclopentadiene, cyclohexadiene, cyclododecadiene, cyclododecatriene, isoprene, 1,5-hexadiene, butadiene, polybutadienes, divinylbenzenes and the like), oligomers of epichlorohydrin and the like, epoxy ethers and polyhydric alcohols Butylene glycols, polyglycols, thiodiglycols, glycerin, pentaerythritol, sorbitol, polyvinyl alcohol, polyallyl alcohol and the like), epoxy ether of polyhydric phenols (resorcinol, hydroquinone, bis (4-hydroxyphenyl) methane, bis (4-hydroxy-3-methylphenyl) methane , Bis (4-hydroxy-3,5-dibromophenyl) methane, bis
- phenylmethane and epoxides which have been prepared by conventional processes from polyunsaturated carboxylic acids or monounsaturated carboxylic acid esters of unsaturated alcohols, glycidyl esters, polyglycidyl esters which can be obtained by polymerizing or copolymerizing glycidyl esters of unsaturated acids or from other acidic compounds (cyanuric acid, diglycidyl sulfide, Trimethylene trisulfone or its derivatives and others) are available.
- polyfunctional epoxy compounds can be reacted individually or in a mixture, if appropriate in the presence of solvents or plasticizers, by the present process or used to prepare dispersions. They can also be used in mixtures with monoepoxides.
- monoepoxides are used in a mixture with the aforementioned epoxy compounds: epoxidized unsaturated hydrocarbons (butylene, cyclohexene, styrene oxide and others), halogen-containing epoxides, such as. B.
- epichlorohydrin epoxy ether of monohydric alcohols (methyl, ethyl, butyl, 2-ethylhexyl, dodecyl alcohol and others), epoxy ether of monohydric phenols (phenol, cresol and other phenols substituted in the o- or p-position), glycidyl esters of unsaturated carboxylic acids , epoxidized esters of unsaturated alcohols or unsaturated carboxylic acids and the acetals of glycidaldehyde.
- the preferred polyhydric phenols are: resorcinol and various bisphenols, which can be obtained by condensing phenol with aldehydes and ketones such as, for. B. formaldehyde, acetaldehyde, acetone, methyl ethyl ketone and. a., receives. Resins of this type are described in US-A-2855159 and 2589245.
- the epoxy resin has an epoxy equivalent of 160-500.
- Suitable polyalkylene polyether polyols b) which can be used for the preparation of the curing agents according to the invention include, for example, the adducts of an alkylene oxide or an alkylene oxide with a polyhydric alcohol.
- Suitable alkylene oxides are, for example, ethylene oxide, propylene oxide, butylene oxide, amylene oxide and hetero- or block copolymers of these oxides, but preferably ethylene oxide.
- Suitable polyhydric alcohols are both aliphatic alcohols individually or in a mixture, e.g.
- Ethylene glycol 1,3-propylene glycol, 1,2-propylene glycol, 1,4-butylene glycol, 1,3-butylene glycol, 1,2-butylene glycol, 1,5-pentanediol, 1,4-pentanediol, 1,3-pentanediol, 1,6-hexanediol, 1,7-heptanediol, glycerin, 1,1,1-trimethylolpropane, 1,1,1-trimethylolethane, hexane-1,2,6-triol, a-methylglucoside, pentaerythritol and sorbitol.
- the polyalkylene polyether polyols can also be prepared from other starting materials, for. B. from tetrahydrofuran and alkylene oxide-tetrahydrofuran copolymers; Epihalohydrins, e.g. Epichlorohydrin and aralkylene oxides, e.g. Styrene oxide.
- the polyalkylene polyether polyols can have either primary or secondary hydroxyl groups and are preferably polyethers made from alkylene oxides having 2 to 6 carbon atoms, e.g. B. polyethylene ether glycols, polypropylene ether glycols and polybutylene ether glycols.
- the polyalkylene polyether polyols can be prepared by any known method, e.g. B. by the method specified by Wurtz 1859 and described in Encyclopedia of Chemical Technology, Vol. 7, pp. 257 to 262, Interscience Publishers, Inc (1951) or in US-A-1922459.
- the average molar mass of component a2 is 200 to 10,000, preferably 800 to 1200.
- aliphatic, cycloaliphatic, araliphatic and heterocyclic amines or mixtures thereof can be reacted as component B with the epoxy-polyalkylene polyether polyol adducts.
- Examples include: aliphatic, saturated or unsaturated, bifunctional amines, e.g. B. lower aliphatic alkylene polyamines, such as ethylenediamine, 1,2-propylenediamine; 1,3-propylene diamine, 1,4-butylene diamine, hexamethylene diamine, 2,2,4- (2,4,4-) trimethyl hexamethylene diamine or polyalkylene polyamines, e.g. B.
- lower aliphatic alkylene polyamines such as ethylenediamine, 1,2-propylenediamine; 1,3-propylene diamine, 1,4-butylene diamine, hexamethylene diamine, 2,2,4- (2,4,4-) trimethyl hexamethylene diamine or polyalkylene polyamines, e.g. B.
- homologous polyethylene-polyamines such as diethylene triamine, triethylene tetramine, tetraethylene pentamine or analogous polypropylene polyamines, such as dipropylene triamine, or polyoxypropylene polyamines and diamines of the general formula H 2 N.CH 2 -X-CH 2 .NH 2 , where X is the divalent radicals means.
- preferred compounds of component B are xylylenediamine, 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane, 2,2,4- (2,4,4, -) - trimethylhexamethylene diamine or polyoxypropylene polyamine and mixtures thereof. It is possible to react all of the amines mentioned with the monounsaturated compound C of the type before the reaction with the epoxy-polyalkylene polyether polyol adduct to convert to so-called cyanoethylated amines and then use them instead of the pure polyamines. However, the route described below is more common. Before the reaction product of polyamines and the epoxy-polyalkylene polyether polyol adduct is reacted with the monounsaturated compound, it may be diluted with water to a solids content of 50.0 to 90% by weight.
- the reaction with the monounsaturated compound is carried out by adding z. B. acrylonitrile at 20 to 70 ° C, wherein after the addition a residence time at elevated temperature, preferably 50 to 70 ° C is appropriate.
- Acrylonitrile or methacrylonitrile are the preferred compounds of component C.
- BF 3 -benzylamine, BF 3 -mono-ethylamine, BF 3 -propylamine and BF 3 -n-butylamine are preferably used.
- a g equivalent of a hydroxyl group to be reacted with a g equivalent of an epoxy group 100 to 1, preferably 15 to 2 mmol, of the BF 3 amine complex are used.
- the reaction of the hydroxyl groups with the epoxy groups can be carried out in the temperature range from 20 to 200 ° C.
- the reaction temperature depends on the respective BF 3 amine complex.
- the reaction temperature when using BF 3 monoethylamine or BF 3 benzylamine is around 130 ° C.
- the mixtures of hydroxyl groups and epoxy group-containing compounds to be reacted are therefore expediently heated to the temperature at which the reaction proceeds at a sufficient rate, ie in 30 minutes to 15 hours.
- the reaction is expediently followed by increasing the epoxy equivalent, which indicates a decrease in the epoxide groups.
- the reaction can be stopped by cooling below the reaction temperature.
- Part of the BF 3 amine complex is consumed during the reaction by incorporating the fluoride ions into the reaction product. Any excess of the BF 3 amine complex can be rendered harmless after the reaction has ended by adding basic-acting substances such as bleaching earth, calcium oxide, calcium hydroxide, barium oxide and barium hydroxide to the complex.
- the basic substances are removed together with the products resulting from them and the BF 3 amine complexes by filtration.
- the reaction of the adduct, which still contains reactive epoxy groups, with the polyamine or the adduct of polyamine and component C is carried out at 20 to 100 ° C., preferably 20 to 40 ° C. Thereafter, a holding time at elevated temperature, preferably 50 to 80 ° C., with stirring for 1 to 3 hours is appropriate.
- the curing agents according to the invention are used, if appropriate together with emulsifying agents, for the preparation of aqueous curable epoxy resin dispersions which are used as coating or coating agents.
- the epoxy resins curable with the curing agents according to the invention can contain further additives, such as, for. B. wetting agents, preferred wetting agents are the commercially available, non-ionic wetting agents based on modified alkylphenol, such as. B. alkylphenoxypoly (ethyleneoxy) ethanol, a condensate of nonylphenol and ethylene oxide, containing 9-10 moles of ethylene oxide per mole of nonylphenol, etc.
- modified alkylphenol such as. B. alkylphenoxypoly (ethyleneoxy) ethanol, a condensate of nonylphenol and ethylene oxide, containing 9-10 moles of ethylene oxide per mole of nonylphenol, etc.
- the epoxy resins are generally introduced into water, so that the dispersion preferably contains up to 50% by weight of water. If a combination of epoxy resin and curing agent according to the invention is used as block filler or if pigments are present, the water content can even be 90% by weight. If colored coating mixtures are produced from epoxy resins and curing agents according to the invention, various additives can be added to the dispersion of epoxy resin and the curing agent according to the invention. These include pigments such as titanium dioxide, iron oxide, fillers such as asbestos, talc, mortar and other cement-like substances, pigment dispersants and other conventional coloring and coating aids.
- the dispersion of epoxy resins and water-based hardening agents according to the invention can be used in any known manner. Suitable methods include: brushing, rolling, spraying, pouring, dipping, squeegees, pressing, filling, electrodeposition, screen printing, etc.
- the dispersion of epoxy resins and hardening agents according to the invention can be used as a base coat, filler, clear sealer, protective coating, coatings, seals, thin mortar, mortar, etc. Their use is particularly expedient where corrosion resistance is desired.
- the dispersions can also be used with epoxy resin / thermoplastic mixtures such as coal tar, vinyl polymers, etc. It can be used as a binder for pressed carbon, conductive floor coverings and leveling compounds, as an adhesive for wood, fabric, leather and metal and for various types of substrates such as cemented floors, walls, swimming pools, glass, glazed bricks etc.
- the epoxy resin dispersion can be mixed with mortar or cement, the water being used as an emulsion to make the cement pasty.
- the water in the cement mixture can be used as a solvent for the epoxy resin dispersion.
- Addition of the hardening agent according to the invention enables uniform mixing of cement and epoxy resin hardener dispersion. It is thus possible to obtain epoxy resin hardener dispersion hardened cement.
- the viscosities are measured at 25 ° C. in a falling ball viscometer according to Höppler.
- the character ⁇ -_ means «approximately» and EV epoxy equivalent weight.
- the viscosity of the product is 9600 mPa.s. This product is used as a preliminary product for the production of the curing agents according to the invention.
- the curing agent obtained is now 82%, has an HAV of 159 and a viscosity of 2330 mPa.s.
- Example 1A was repeated. After a 4.5 hour hold time at 170 ° C, an EV value of 391 was obtained.
- the curing agent obtained is now 81.5%, has an HAV of 197 and a viscosity of 13450 m.Pa.s.
- Example 4 C The procedure was as described in Example 3 C.
- the curing agent obtained is 81.5%, has an HAV of 197 and a viscosity of 13120 mPa.s.
- Example 3 A and B were repeated.
- Example 1 A and B Example 1 A and B were repeated.
- Example 12 C 590 g of the 80% solution are now reacted with 53 g of acrylonitrile (0.2 val per hydrogen amine) as described under Example 1 C.
- the HAV is now 161
- the viscosity is 3940 mPa.s. 1.25 val each, based on epoxy groups, of the precursors listed under Example 13 A to 19 A were followed up with 136 g xylylenediamine (2 val) and 170 g 1-amino-3-aminomethyl-3,5,5-trimethylcyclohexane (2 val)
- Example 3 B implemented.
- Products 13B to 19B were implemented according to Example 3C.
- the dispersions showed excellent stability within the processing time (i.e. until the start of the crosslinking reaction between the resin and hardener components), which was 30 minutes to 5 hours.
- the aqueous dispersions using epoxy resin A were applied in a layer thickness of approximately 200 pm to phosphated iron sheets and asbestos-cement plates.
- the dispersions showed excellent stability within the processing time (i.e. until the start of the crosslinking reaction between the resin and hardener components), which was 30 minutes to 3 hours.
- the emulsion paint produced with epoxy resin A and the films produced therefrom showed test results similar to those with epoxy resin C.
- pot life was used to denote the time which elapsed until a dispersion composed of 50 g of the epoxy resin, 50 g of water and an equivalent amount of the particular curing agent according to the invention, Example 1 C to 19 C, or until the viscosity of the dispersion was so strong it has increased that their proper processing is no longer possible.
- a mixture consisting of 80 g of fine-grained quartz sand (grain size 0.5 mm), 160 g of coarse-grained quartz sand, 80 g of cement, 11 g of epoxy resin B and 11.7 g of the curing agent according to Example 3 C according to the invention were mixed homogeneously in a mixer and mixed with 80 g Water mixed to a pasty consistency.
- This mass was processed with a squeegee to an approximately 5mm thick concrete floor covering, which after curing had excellent oil and water resistance.
- the tensile, compressive and flexural strengths of the concrete mixture are improved by the addition of the epoxy resin hardener dispersion by approx. 20%.
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Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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CH8853/77 | 1977-07-18 | ||
CH885377 | 1977-07-18 |
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EP0000605A1 EP0000605A1 (de) | 1979-02-07 |
EP0000605B1 true EP0000605B1 (de) | 1983-04-06 |
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EP78200101A Expired EP0000605B1 (de) | 1977-07-18 | 1978-07-17 | Härtungsmittel für wässerige Epoxydharzdispersionen, deren Herstellung und Verwendung |
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US (1) | US4197389A (ja) |
EP (1) | EP0000605B1 (ja) |
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IT (1) | IT1097871B (ja) |
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BR112014032644A2 (pt) | 2012-06-29 | 2017-06-27 | Dow Global Technologies Llc | dispersão aquosa de resina epoxídica, processo de dispersão aquosa, composição de revestimento, e, composição de cimento |
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US3993707A (en) * | 1973-10-23 | 1976-11-23 | Pacific Vegetable Oil Corporation | Composition for coating wet surfaces or surfaces immersed in water |
US4123402A (en) * | 1975-02-27 | 1978-10-31 | The O'brien Corporation | Curing agent for water-based epoxy resins |
JP3302453B2 (ja) * | 1993-07-12 | 2002-07-15 | マツダ株式会社 | 車両のルーフ昇降装置 |
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1978
- 1978-07-12 US US05/924,050 patent/US4197389A/en not_active Expired - Lifetime
- 1978-07-17 IT IT25810/78A patent/IT1097871B/it active
- 1978-07-17 DE DE7878200101T patent/DE2862222D1/de not_active Expired
- 1978-07-17 EP EP78200101A patent/EP0000605B1/de not_active Expired
- 1978-07-17 JP JP8621078A patent/JPS5456700A/ja active Granted
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Cited By (28)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0387418A3 (de) * | 1989-03-13 | 1991-07-31 | Rütgerswerke Aktiengesellschaft | Härtungsmittel für Epoxidverbindungen, ihre Herstellung und Verwendung |
EP0387418A2 (de) * | 1989-03-13 | 1990-09-19 | Rütgerswerke Aktiengesellschaft | Härtungsmittel für Epoxidverbindungen, ihre Herstellung und Verwendung |
US5854312A (en) * | 1992-04-21 | 1998-12-29 | Air Products And Chemicals, Inc. | Aqueous hardeners for epoxy resin systems |
EP0610787A2 (de) * | 1993-02-08 | 1994-08-17 | Hoechst Aktiengesellschaft | Härtungsmittel für wässrige Epoxidharz-Dispersionen |
US5539023A (en) * | 1993-02-08 | 1996-07-23 | Hoechst Aktiengesellschaft | Curing agents for aqueous epoxy resin dispersions |
EP0618245A2 (de) * | 1993-03-29 | 1994-10-05 | Hoechst Aktiengesellschaft | Polyol-Epoxid Additionsprodukte zur Verwendung als Emulgator für flüssige Epoxidharze |
US5459180A (en) * | 1993-03-29 | 1995-10-17 | Hoechst Ag | Polyol/epoxy adducts for use as emulsifier for liquid epoxy resins |
EP0694579A2 (de) | 1994-06-30 | 1996-01-31 | Hoechst Aktiengesellschaft | Stabile, wässrige Epoxidharz-Dispersion, Verfahren zu deren Herstellung und deren Verwendung |
US5670612A (en) * | 1994-10-28 | 1997-09-23 | Mitsubishi Gas Chemical Company, Inc. | Polyamine/epoxy-containing polyoxyethylene/hydrophobic epoxy adduct curing agent |
DE19525826C1 (de) * | 1995-07-15 | 1996-10-24 | Herberts Gmbh | Wäßriges zweikomponentiges Überzugsmittel und dessen Verwendung bei Verfahren zur Herstellung von Mehrschichtlackierungen |
EP0768348A2 (de) * | 1995-09-29 | 1997-04-16 | Vianova Resins GmbH | Wässrige Beschichtungsmittel auf der Basis lösemittelarmer modifizierter Epoxidharz-Dispersionen |
US5906864A (en) * | 1996-06-25 | 1999-05-25 | Herberts Gesellschaft Mit Beschrankter Haftung | Aqueous coating composition and its use to produce filler coats |
US6008314A (en) * | 1996-06-25 | 1999-12-28 | Herberts Gmbh | Aminourethane hardeners, epoxide-based coating media and the use thereof |
US6395806B1 (en) | 1998-07-07 | 2002-05-28 | Cognis Deutschland Gmbh | Hardeners for epoxy resins, processes for producing the same and methods of using the same |
US6387988B1 (en) | 1998-07-07 | 2002-05-14 | Cognis Deutschland Gmbh | Epoxy resin hardener from aminopolyalkylene oxide/unsaturated ester, polyepoxide and amine |
US6387989B1 (en) | 1998-07-07 | 2002-05-14 | Cognis Deutschland Gmbh | Hardeners for epoxy resins, processes for producing the same and methods of using the same |
EP0995767A3 (de) * | 1998-10-19 | 2001-01-10 | U. Prümmer Polymer-Chemie GmbH | Härtungsmittel für wässrige Epoxidharzdispersionen |
EP0995767A2 (de) * | 1998-10-19 | 2000-04-26 | U. Prümmer Polymer-Chemie GmbH | Härtungsmittel für wässrige Epoxidharzdispersionen |
US6235931B1 (en) | 1998-12-30 | 2001-05-22 | Shell Oil Company | Partial oxidation of polyoxyalkylene polyol compositions to polycarboxylic acid compositions |
US6653436B2 (en) | 2000-12-08 | 2003-11-25 | Resolution Performance Products Llc | Water dispersible epoxy resins |
US6653369B2 (en) | 2001-06-15 | 2003-11-25 | Solutia Austria Gmbh | Water dilutable amine curing agents for aqueous two component epoxy resin systems |
US6911490B2 (en) | 2001-11-30 | 2005-06-28 | Solutia Austria Gmbh | Aqueous curing agents for aqueous epoxy resin dispersions |
EP1803760A1 (en) | 2005-12-30 | 2007-07-04 | Cytec Surface Specialties Austria GmbH | Aqueous aminic curing agent for epoxy resins |
EP2520599A1 (en) | 2011-05-05 | 2012-11-07 | Cytec Austria GmbH | Multifunctional primary amine, process for its preparation, and use thereof |
WO2012150312A1 (en) | 2011-05-05 | 2012-11-08 | Cytec Austria Gmbh | Multifunctional primary amine, process for its preparation, and use thereof |
EP2727968A1 (en) | 2012-11-06 | 2014-05-07 | ALLNEX AUSTRIA GmbH | Multifunctional primary amine, process for its preparation, and use thereof |
WO2014072308A2 (en) | 2012-11-06 | 2014-05-15 | Allnex Austria Gmbh | Aqueous dispersions of a multifunctional primary amine, process for its preparation, and use therof |
WO2019097039A1 (en) | 2017-11-19 | 2019-05-23 | Allnex Austria Gmbh | Multi-layer coatings and coating compositions therefor |
Also Published As
Publication number | Publication date |
---|---|
DE2862222D1 (en) | 1983-05-11 |
IT7825810A0 (it) | 1978-07-17 |
EP0000605A1 (de) | 1979-02-07 |
JPS6140688B2 (ja) | 1986-09-10 |
IT1097871B (it) | 1985-08-31 |
JPS5456700A (en) | 1979-05-07 |
US4197389A (en) | 1980-04-08 |
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