ES2237437T3 - Endurecedor aminico para resinas epoxi. - Google Patents
Endurecedor aminico para resinas epoxi.Info
- Publication number
- ES2237437T3 ES2237437T3 ES00944045T ES00944045T ES2237437T3 ES 2237437 T3 ES2237437 T3 ES 2237437T3 ES 00944045 T ES00944045 T ES 00944045T ES 00944045 T ES00944045 T ES 00944045T ES 2237437 T3 ES2237437 T3 ES 2237437T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- residue
- compound
- cycloaliphatic
- aliphatic
- 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 - Lifetime
Links
- 229920000647 polyepoxide Polymers 0.000 title claims description 26
- 239000003822 epoxy resin Substances 0.000 title claims description 24
- 239000004848 polyfunctional curative Substances 0.000 title description 16
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 2
- -1 n-octyl Chemical group 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 38
- 150000001412 amines Chemical class 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 23
- 239000004593 Epoxy Substances 0.000 claims description 18
- 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 18
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 150000003553 thiiranes Chemical class 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 229920000768 polyamine Polymers 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 9
- 239000011347 resin Substances 0.000 claims description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 8
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229920003986 novolac Polymers 0.000 claims description 6
- 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 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229930003836 cresol Natural products 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 238000005266 casting Methods 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 239000002131 composite material Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 150000002118 epoxides Chemical class 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000002253 acid Substances 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
- 239000007788 liquid Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000003580 L-valyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C(C([H])([H])[H])(C([H])([H])[H])[H] 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 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 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000000753 cycloalkyl group Chemical group 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 150000002334 glycols Chemical class 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 238000006748 scratching Methods 0.000 description 3
- 230000002393 scratching effect Effects 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 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 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical group CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 238000005191 phase separation Methods 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
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PFYHYHZGDNWFIF-UHFFFAOYSA-N (+)-DMDP Natural products OCC1NC(CO)C(O)C1O PFYHYHZGDNWFIF-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- 125000005838 1,3-cyclopentylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:2])C([H])([H])C1([H])[*:1] 0.000 description 1
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 description 1
- PISLZQACAJMAIO-UHFFFAOYSA-N 2,4-diethyl-6-methylbenzene-1,3-diamine Chemical compound CCC1=CC(C)=C(N)C(CC)=C1N PISLZQACAJMAIO-UHFFFAOYSA-N 0.000 description 1
- PFYHYHZGDNWFIF-KVTDHHQDSA-N 2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine Chemical compound OC[C@H]1N[C@H](CO)[C@@H](O)[C@@H]1O PFYHYHZGDNWFIF-KVTDHHQDSA-N 0.000 description 1
- JWTVQZQPKHXGFM-UHFFFAOYSA-N 2,5-dimethylhexane-2,5-diamine Chemical compound CC(C)(N)CCC(C)(C)N JWTVQZQPKHXGFM-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- SZCFDTYKNQJQKT-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC2OC2C1OCC1CO1 SZCFDTYKNQJQKT-UHFFFAOYSA-N 0.000 description 1
- BGYGNVSBGRDARU-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCC1OC1 BGYGNVSBGRDARU-UHFFFAOYSA-N 0.000 description 1
- XORJNZNCVGHBDZ-UHFFFAOYSA-N 2-[2-(6-oxabicyclo[3.1.0]hexan-2-yloxy)ethoxy]-6-oxabicyclo[3.1.0]hexane Chemical compound C1CC2OC2C1OCCOC1C2OC2CC1 XORJNZNCVGHBDZ-UHFFFAOYSA-N 0.000 description 1
- OJPDDQSCZGTACX-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)anilino]ethanol Chemical compound OCCN(CCO)C1=CC=CC=C1 OJPDDQSCZGTACX-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- MBNVSWHUJDDZRH-UHFFFAOYSA-N 2-methylthiirane Chemical compound CC1CS1 MBNVSWHUJDDZRH-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- PFYHYHZGDNWFIF-OMMKOOBNSA-N 2R,5R-Dihydroxymethyl-3R,4R-dihydroxy-pyrrolidine Natural products OC[C@@H]1N[C@@H](CO)[C@H](O)[C@@H]1O PFYHYHZGDNWFIF-OMMKOOBNSA-N 0.000 description 1
- 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 description 1
- RXBBSTXUVVVWRC-UHFFFAOYSA-N 3-[3-[4,4-dimethyl-3-(oxiran-2-ylmethyl)-2,5-dioxoimidazolidin-1-yl]-2-(oxiran-2-ylmethoxy)propyl]-5,5-dimethyl-1-(oxiran-2-ylmethyl)imidazolidine-2,4-dione Chemical compound O=C1N(CC(CN2C(C(C)(C)N(CC3OC3)C2=O)=O)OCC2OC2)C(=O)C(C)(C)N1CC1CO1 RXBBSTXUVVVWRC-UHFFFAOYSA-N 0.000 description 1
- NVOQLEBSTHAENC-UHFFFAOYSA-N 3-[6-(3-aminopropoxy)hexoxy]propan-1-amine Chemical compound NCCCOCCCCCCOCCCN NVOQLEBSTHAENC-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 description 1
- KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-UHFFFAOYSA-N 0.000 description 1
- NWIVYGKSHSJHEF-UHFFFAOYSA-N 4-[(4-amino-3,5-diethylphenyl)methyl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=C(CC)C=2)=C1 NWIVYGKSHSJHEF-UHFFFAOYSA-N 0.000 description 1
- JHCBFGGESJQAIQ-UHFFFAOYSA-N 4-[(4-amino-3,5-dimethylcyclohexyl)methyl]-2,6-dimethylcyclohexan-1-amine Chemical compound C1C(C)C(N)C(C)CC1CC1CC(C)C(N)C(C)C1 JHCBFGGESJQAIQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- XDDVRYDDMGRFAZ-UHFFFAOYSA-N thiobenzophenone Chemical compound C=1C=CC=CC=1C(=S)C1=CC=CC=C1 XDDVRYDDMGRFAZ-UHFFFAOYSA-N 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- VYNGFCUGSYEOOZ-UHFFFAOYSA-N triphenylphosphine sulfide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=S)C1=CC=CC=C1 VYNGFCUGSYEOOZ-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical class [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- 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
- C08G59/56—Amines together with other curing agents
-
- 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
- C08G59/66—Mercaptans
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1389/99 | 1999-07-28 | ||
| CH138999 | 1999-07-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2237437T3 true ES2237437T3 (es) | 2005-08-01 |
Family
ID=4209292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES00944045T Expired - Lifetime ES2237437T3 (es) | 1999-07-28 | 2000-07-20 | Endurecedor aminico para resinas epoxi. |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US6759506B1 (https=) |
| EP (1) | EP1200502B1 (https=) |
| JP (1) | JP2003506337A (https=) |
| KR (1) | KR100689991B1 (https=) |
| CN (1) | CN1203105C (https=) |
| AT (1) | ATE290560T1 (https=) |
| AU (1) | AU766332B2 (https=) |
| BR (1) | BR0013182A (https=) |
| CA (1) | CA2380296A1 (https=) |
| DE (1) | DE50009735D1 (https=) |
| ES (1) | ES2237437T3 (https=) |
| HU (1) | HUP0201978A3 (https=) |
| MX (1) | MXPA02000894A (https=) |
| PL (1) | PL353277A1 (https=) |
| TR (1) | TR200200163T2 (https=) |
| TW (1) | TW487715B (https=) |
| WO (1) | WO2001009221A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2431558A1 (en) * | 2001-01-29 | 2002-08-08 | Vantico Ag | Gel coat composition |
| CN100341969C (zh) * | 2004-01-02 | 2007-10-10 | 湖南神力实业有限公司 | 快速固化双组份环氧胶粘剂及制备方法 |
| KR100804293B1 (ko) * | 2004-03-31 | 2008-02-18 | 아사히 가세이 케미칼즈 가부시키가이샤 | 에폭시 수지용 경화제 및 에폭시 수지 조성물 |
| DE102007012919B4 (de) * | 2007-03-19 | 2015-03-19 | Robert Bosch Gmbh | Zündspule |
| DE102007018414A1 (de) * | 2007-04-17 | 2008-10-23 | Wakol Gmbh | Parkettfugenkittsystem und Verfahren zur Herstellung eines Parkettfugenkitts |
| DE102009028019A1 (de) | 2009-02-04 | 2010-08-05 | Evonik Degussa Gmbh | Härtbare Zusammensetzungen auf Basis von Epoxidharzen und hetero-poly-cyclischen Polyaminen |
| EP2480586B1 (en) * | 2009-09-22 | 2014-11-12 | Dow Global Technologies LLC | Process for preparing episulfide resins |
| BR112017018406A2 (pt) | 2015-02-27 | 2018-04-17 | 3M Innovative Properties Co | adesivo estrutural em duas partes |
| CN107406576B (zh) | 2015-02-27 | 2019-04-26 | 3M创新有限公司 | 包含增韧的固化剂的双组分粘合剂 |
| ES2767281T3 (es) * | 2016-06-23 | 2020-06-17 | Evonik Operations Gmbh | Bloque de construcción reforzado hecho de hormigón aireado sometido a autoclave (AAC) |
| WO2019060513A1 (en) * | 2017-09-20 | 2019-03-28 | Ppg Industries Ohio, Inc. | A COUPLING LAYER COMPOSITION COMPRISING A POLYTHIOL |
| US11149108B1 (en) | 2018-06-26 | 2021-10-19 | National Technology & Engineering Solutions Of Sandia, Llc | Self-assembly assisted additive manufacturing of thermosets |
| KR102867642B1 (ko) * | 2023-01-11 | 2025-10-13 | 한국화학연구원 | 다관능성 아민 경화제 및 이를 포함하는 에폭시 수지 조성물 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2831830A (en) | 1954-05-24 | 1958-04-22 | Shell Dev | Sulfur-containing resinous products from polyepoxides |
| GB1082565A (en) * | 1965-04-07 | 1967-09-06 | Ciba Ltd | Epoxy resin compositions |
| US3548002A (en) * | 1968-07-10 | 1970-12-15 | Dow Chemical Co | Thiol alkylene amines |
| US3919277A (en) * | 1973-03-21 | 1975-11-11 | Polaroid Corp | Mercaptoethylation of amines |
| CH586732A5 (en) * | 1974-02-21 | 1977-04-15 | Sika Ag | Storable liq. episulphide resins - from mixts. of epoxy resins and thiourea in solvent soln. |
| JPS5182400A (ja) * | 1975-01-17 | 1976-07-19 | Asahi Denka Kogyo Kk | Kokaseiehokishijushisoseibutsu |
| DE3639488A1 (de) * | 1986-11-18 | 1988-05-19 | Basf Lacke & Farben | Kathodisch abscheidbare wasserverduennbare bindemittel, wasserverduennbare ueberzugszusammensetzungen und verfahren zur herstellung von kathodisch abscheidbaren wasserverduennbaren bindemitteln |
| DE3644371A1 (de) * | 1986-12-24 | 1988-07-07 | Hoechst Ag | Aminogruppenhaltige derivate von 1,3-bissubstituiertem propanol-2, verfahren zu ihrer herstellung und ihre verwendung |
| US4879414A (en) * | 1988-02-17 | 1989-11-07 | Henkel Corporation | Polythiols and use as epoxy resin curing agents |
| EP0370446B1 (de) | 1988-11-23 | 1996-05-15 | Ciba-Geigy Ag | Polyoxyalkylendithiole und Polyamine enthaltende härtbare Epoxidharz-Stoffgemische |
| KR100193147B1 (ko) | 1990-03-30 | 1999-06-15 | 월터클라웨인, 한느-피터 위트린 | 개질된 에폭시 수지 |
| JPH04124170A (ja) * | 1990-09-13 | 1992-04-24 | Nippon Shokubai Co Ltd | 多官能チオール化合物及びその製法 |
| JP3247741B2 (ja) * | 1992-12-17 | 2002-01-21 | 株式会社日本触媒 | エポキシ樹脂硬化剤 |
| JPH06184090A (ja) * | 1992-12-17 | 1994-07-05 | Nippon Shokubai Co Ltd | 含硫黄化合物およびその製造方法 |
| JPH07173283A (ja) * | 1993-12-17 | 1995-07-11 | Nippon Shokubai Co Ltd | 変性ポリアミドポリアミンの製造方法 |
| JPH07228567A (ja) * | 1993-12-21 | 1995-08-29 | Nippon Shokubai Co Ltd | 含硫黄化合物およびその製造方法 |
-
2000
- 2000-07-20 AU AU58287/00A patent/AU766332B2/en not_active Ceased
- 2000-07-20 DE DE50009735T patent/DE50009735D1/de not_active Expired - Lifetime
- 2000-07-20 BR BR0013182-2A patent/BR0013182A/pt not_active IP Right Cessation
- 2000-07-20 CA CA002380296A patent/CA2380296A1/en not_active Abandoned
- 2000-07-20 MX MXPA02000894A patent/MXPA02000894A/es not_active Application Discontinuation
- 2000-07-20 KR KR1020027000979A patent/KR100689991B1/ko not_active Expired - Fee Related
- 2000-07-20 HU HU0201978A patent/HUP0201978A3/hu unknown
- 2000-07-20 AT AT00944045T patent/ATE290560T1/de not_active IP Right Cessation
- 2000-07-20 PL PL00353277A patent/PL353277A1/xx not_active Application Discontinuation
- 2000-07-20 ES ES00944045T patent/ES2237437T3/es not_active Expired - Lifetime
- 2000-07-20 TR TR2002/00163T patent/TR200200163T2/xx unknown
- 2000-07-20 JP JP2001514025A patent/JP2003506337A/ja active Pending
- 2000-07-20 EP EP00944045A patent/EP1200502B1/de not_active Expired - Lifetime
- 2000-07-20 WO PCT/EP2000/006931 patent/WO2001009221A1/de not_active Ceased
- 2000-07-20 US US10/031,983 patent/US6759506B1/en not_active Expired - Lifetime
- 2000-07-20 CN CNB008108110A patent/CN1203105C/zh not_active Expired - Fee Related
- 2000-07-26 TW TW089114886A patent/TW487715B/zh active
-
2004
- 2004-03-31 US US10/815,532 patent/US7223820B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0201978A2 (en) | 2002-09-28 |
| EP1200502A1 (de) | 2002-05-02 |
| DE50009735D1 (de) | 2005-04-14 |
| AU766332B2 (en) | 2003-10-16 |
| AU5828700A (en) | 2001-02-19 |
| PL353277A1 (en) | 2003-11-03 |
| CA2380296A1 (en) | 2001-02-08 |
| KR100689991B1 (ko) | 2007-03-09 |
| CN1203105C (zh) | 2005-05-25 |
| US7223820B2 (en) | 2007-05-29 |
| WO2001009221A1 (de) | 2001-02-08 |
| TR200200163T2 (tr) | 2002-05-21 |
| US6759506B1 (en) | 2004-07-06 |
| HUP0201978A3 (en) | 2005-02-28 |
| TW487715B (en) | 2002-05-21 |
| CN1376172A (zh) | 2002-10-23 |
| MXPA02000894A (es) | 2002-08-06 |
| BR0013182A (pt) | 2002-04-02 |
| US20040186268A1 (en) | 2004-09-23 |
| ATE290560T1 (de) | 2005-03-15 |
| KR20020021163A (ko) | 2002-03-18 |
| JP2003506337A (ja) | 2003-02-18 |
| EP1200502B1 (de) | 2005-03-09 |
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