FI97145B - Härdningskomponenter för syntetiska hartser och deras användning - Google Patents
Härdningskomponenter för syntetiska hartser och deras användning Download PDFInfo
- Publication number
- FI97145B FI97145B FI881615A FI881615A FI97145B FI 97145 B FI97145 B FI 97145B FI 881615 A FI881615 A FI 881615A FI 881615 A FI881615 A FI 881615A FI 97145 B FI97145 B FI 97145B
- Authority
- FI
- Finland
- Prior art keywords
- alkyl
- curing component
- group
- groups
- formula
- Prior art date
Links
- 229920003002 synthetic resin Polymers 0.000 title description 6
- 239000000057 synthetic resin Substances 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 239000012948 isocyanate Substances 0.000 claims abstract description 19
- 229920000768 polyamine Polymers 0.000 claims abstract description 18
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 16
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims abstract description 8
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical group O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000000654 additive Substances 0.000 claims abstract description 5
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 5
- 239000003085 diluting agent Substances 0.000 claims abstract description 4
- 239000000047 product Substances 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 150000002118 epoxides Chemical class 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 239000004922 lacquer Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims 2
- 101150047265 COR2 gene Proteins 0.000 claims 1
- 101100467189 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) QCR2 gene Proteins 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 6
- 239000003973 paint Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- -1 x being CN Chemical group 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 13
- 238000004821 distillation Methods 0.000 description 11
- 239000004848 polyfunctional curative Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 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 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 239000005056 polyisocyanate Substances 0.000 description 7
- 229920001228 polyisocyanate Polymers 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical group CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 125000005442 diisocyanate group Chemical group 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 125000005587 carbonate group Chemical group 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000005676 cyclic carbonates Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KMBPCQSCMCEPMU-UHFFFAOYSA-N n'-(3-aminopropyl)-n'-methylpropane-1,3-diamine Chemical compound NCCCN(C)CCCN KMBPCQSCMCEPMU-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical class O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-dioxonaphthalene Natural products C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- BOKGTLAJQHTOKE-UHFFFAOYSA-N 1,5-dihydroxynaphthalene Chemical compound C1=CC=C2C(O)=CC=CC2=C1O BOKGTLAJQHTOKE-UHFFFAOYSA-N 0.000 description 1
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- ZPANWZBSGMDWON-UHFFFAOYSA-N 1-[(2-hydroxynaphthalen-1-yl)methyl]naphthalen-2-ol Chemical compound C1=CC=C2C(CC3=C4C=CC=CC4=CC=C3O)=C(O)C=CC2=C1 ZPANWZBSGMDWON-UHFFFAOYSA-N 0.000 description 1
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- IFQLLGFCFOQPFA-UHFFFAOYSA-N 2-[3-[3-(oxiran-2-yl)nonan-3-yloxy]nonan-3-yl]oxirane Chemical compound C1OC1C(CC)(CCCCCC)OC(CC)(CCCCCC)C1CO1 IFQLLGFCFOQPFA-UHFFFAOYSA-N 0.000 description 1
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-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
- 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 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical class 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
- QZWKEPYTBWZJJA-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine-4,4'-diisocyanate Chemical compound C1=C(N=C=O)C(OC)=CC(C=2C=C(OC)C(N=C=O)=CC=2)=C1 QZWKEPYTBWZJJA-UHFFFAOYSA-N 0.000 description 1
- FNVOFDGAASRDQY-UHFFFAOYSA-N 3-amino-2,2-dimethylpropan-1-ol Chemical compound NCC(C)(C)CO FNVOFDGAASRDQY-UHFFFAOYSA-N 0.000 description 1
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- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Photoreceptors In Electrophotography (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
- Saccharide Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Claims (13)
1. Aminogrupper innehällande härdningskomponent (A) för föreningar (B), som innehäller epoxid- eller 1,3-di- 5 oxolan-2-on-grupper, kännetecknad av, att härdningskomponenten (A) är en reaktionsprodukt av (ax) CH-aktiva alkylestrar eller av addukter av CH-aktiva alkyl-estrar och isocyanat med (a2) polyaminer.
2. Härdningskomponenten enligt patentkrav 1, 10 kännetecknad av, att (a1) har formeln I, \ CH - y \ J 15. m väri Rx är en kolvätegrupp med 1-12 C-atomer; x är CN, C0NH2, CONRiH, CONR^' , COR^ R1C=NR1' eller N02, varvid Ra och R:' kan vara samma eller olika och betecknar Sainina som ovan; 20 y är väte eller Rx med den ovanstäende betydelsen, varvid m=l i bäda fallen; O tl eller (C-NH)n - R2, väri R2 är en n-värd kolvätegrupp, som eventuellt kan vara avbruten av heteroatomer (O,N), och 25 m®n>l, företrädesvis 1-10.
3. Härdningskomponent enligt patentkrav 2, kännetecknad av, att i formeln I Rj är en (Cj-Ce)-alkyl, x är en C00-(Ci-C6)-alkyl eller CO-(C^-Cg) -alkyl och y O 30 är väte eller (C-NH)n - R2. • 4. Härdningskomponent enligt patentkrav 2 eller 3, kännetecknad av, att n är 1, 2 eller 3.
5. Härdningskomponent enligt nägot av patentkraven 1-4, kännetecknad av, att (ax) en adduk-35 tionsprodukt av en ester av malonsyra, acetättiksyra eller 97145 cyanättiksyra med 1-6 C-atomer i estergruppen, eller en adduktionsprodukt av dessa föreningar och isocyanater.
6. Härdningskomponent enligt ndgot av patentkraven 1-5, kännetecknad av, att (a2) har minst tvd 5 primära aminogrupper eller en primär och en sekundär ami-nogrupp.
7. Härdningskomponent enligt nägot av patentkraven 1-6, kännetecknad av, att (a2) har formeln il, 10 H2N-(R3NH)p-R4 II väri p är 0 eller ett heltal 1-6, företrädesvis 1-4, R3 är en tvävärd, företrädesvis icke-aromatisk kolvätegrupp 15 med 2-18 C-atomer, företrädesvis en förgrenad eller oförgrenad alkylengrupp med 2-10 C-atomer, eller en cyk-loalkylengrupp med 5-12 C-atomer, eller en aralkylen-grupp med 7-12 C-atomer, och Λ
20 R, är H eller -R,-N ' varl 9ruppen R, betecknar samma som ovan och R5 och R6 är oberoende av va-randra H, en (C3 - C20)-alkyl, hydroxi-(C3 - C16)-alkyl, företrädesvis -CH2-CH-R6 (R6 är H, en (03 - C12)-alkyl,
25 OH O 0^-0-(^ - C12)-alkyl, -CH2-0-aryl, -CHj-O-C-iCj - C12)-alkyl eller CH2-CH-CN (R7 är H eller (C^Cg)-alkyl) eller R5 och R6 R7 är en del av en alifatisk ring med 5, 6 eller 7 medlemmar 30 sd, att om m är 0, R4 är inte H.
8. Härdningskomponent enligt ndgot av patentkraven 1-7, kännetecknad av, att förhdllande mel-lan esterekvivalenter av (a3) samt eventuellt närvarande C=0-eller Ν=Η3'-ekvivalenter och aminekvivalenter av (a2) 35 är 1:2 - 1:20. li Itu I Itl tlt ai ; : 27 97145
9. Härdningskomponent enligt nägot av patentkraven 1-7, kännetecknad av, att den har formeln III
5 Z' *s S N \ (iii) \ cal- y \ z ' / · 10 väri y och m betecknar sanuna som i formeln I, R3, R4 och p betecknar samma som i formeln II, R5 är väte eller samma som i formeln I; O R5 " I z är väte, CN, C-N-( R3NH)p-R4, CONH2, CONR^, CONRjRj ' , C0R3 15 eller R1C=NR1', om y är H eller Rx? O Rs -f z är väte, CN, C-N-(R3NH)p-R4, C0NH2, CONRjH eller CONRjRj ', 0 om y är (C-NH)n-R2. 20 10. Härdningsbar blandning, som är baserad pä en härdningskomponent (A), en förening (B), som innehäller epoxid- och/eller 1,3-dioxolan-2-on-grupper, eventuellt ett utspädningsmedel (C) samt eventuella tillsattsämnen (D), kännetecknad av, att komponenten (A) som 25 en härdningskomponent är enligt nägot av patentkraven 1 -8.
11. Härdningsbar blandning enligt patentkrav 10, kännetecknad av, att härdningskomponenten (A) redan har reagerat med en del av föreningen (B). 30 12. Härdningsbar blandning enligt patentkrav 10 eller 11, kännetecknad av, att komponenten (B) är ett epoxidharts med en medelmolekylvikt (Μ„) av cir-ka 300 - 20000.
13. Användning av en härdningskomponent enligt nä-35 got av patentkraven 1 - 9 i härdningsbara blandningar, speciellt i lackprodukter.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3711947 | 1987-04-09 | ||
| DE19873711947 DE3711947A1 (de) | 1987-04-09 | 1987-04-09 | Haertungskomponente fuer kunstharze und deren verwendung |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI881615A0 FI881615A0 (sv) | 1988-04-07 |
| FI881615L FI881615L (sv) | 1988-10-10 |
| FI97145B true FI97145B (sv) | 1996-07-15 |
| FI97145C FI97145C (sv) | 1996-10-25 |
Family
ID=6325196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI881615A FI97145C (sv) | 1987-04-09 | 1988-04-07 | Härdningskomponenter för syntetiska hartser och deras användning |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4859788A (sv) |
| EP (1) | EP0286933B1 (sv) |
| JP (1) | JP2610644B2 (sv) |
| AT (1) | ATE101403T1 (sv) |
| AU (1) | AU601833B2 (sv) |
| CA (1) | CA1340337C (sv) |
| DE (2) | DE3711947A1 (sv) |
| DK (1) | DK193188A (sv) |
| ES (1) | ES2061538T3 (sv) |
| FI (1) | FI97145C (sv) |
| IE (1) | IE61573B1 (sv) |
| NO (1) | NO171683C (sv) |
| PT (1) | PT87200B (sv) |
| ZA (1) | ZA882444B (sv) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5134205A (en) * | 1987-03-02 | 1992-07-28 | King Industries | Certain hydroxyalkyl carbamate compounds, homopolymers and copolymers thereof and uses thereof |
| US5844165A (en) * | 1987-03-26 | 1998-12-01 | Thiokol Corporation | Energetic nitro malonate polyester binders |
| DE3733552A1 (de) * | 1987-10-03 | 1989-04-13 | Herberts Gmbh | Kathodisch abscheidbares waessriges elektrotauchlack-ueberzugsmittel und dessen verwendung |
| DE3734916A1 (de) * | 1987-10-15 | 1989-04-27 | Hoechst Ag | Haertungskomponente fuer kunstharze, diese enthaltende haertbare mischungen sowie deren verwendung |
| US5888654A (en) * | 1988-02-08 | 1999-03-30 | Courtaulds Performance Films | High performance epoxy based laminating adhesive |
| DE3909593A1 (de) | 1989-03-23 | 1990-09-27 | Hoechst Ag | Bindemittel, ihre herstellung und anwendung in haertbaren mischungen |
| ATE96158T1 (de) * | 1989-04-26 | 1993-11-15 | Bayer Ag | Bindemittelkombinationen, ein verfahren zu ihrer herstellung und ihre verwendung. |
| JPH06102765B2 (ja) * | 1990-03-26 | 1994-12-14 | 新日鐵化学株式会社 | 無溶剤型塗料組成物 |
| DE4342721A1 (de) * | 1993-12-15 | 1995-06-22 | Hoechst Ag | Elastisches Epoxidharz-Härter-System |
| DE4342722A1 (de) * | 1993-12-15 | 1995-06-22 | Hoechst Ag | Elastisches Epoxidharz-Härter-System |
| ES2131623T5 (es) * | 1993-12-21 | 2006-08-01 | Basf Corporation | Composicion de revestimiento endurecible de carbonatos ciclicos. |
| DE4343885A1 (de) * | 1993-12-22 | 1995-06-29 | Hoechst Ag | Wäßrige, strahlenhärtbare Bindemitteldispersionen |
| NL1002008C2 (nl) * | 1996-01-02 | 1997-07-03 | Akzo Nobel Nv | Thermohardende poedercoatingsamenstelling. |
| US7049387B2 (en) * | 2001-10-16 | 2006-05-23 | Georgia-Pacific Resins, Inc. | Cure accelerator system for phenolic resins |
| DE10252627A1 (de) | 2002-11-11 | 2004-05-27 | Surface Specialties Germany Gmbh & Co. Kg | Bindemittel und ihre Anwendung als Beschichtungsmaterial für die Beschichtung von Metallbehältern |
| JP3914211B2 (ja) * | 2004-03-03 | 2007-05-16 | 株式会社東芝 | ホログラム記録媒体 |
| EP1755384A1 (en) * | 2004-06-14 | 2007-02-28 | Monsanto Technology, LLC | Microcapsules having activated release of core material therein |
| JP4185026B2 (ja) * | 2004-07-16 | 2008-11-19 | 株式会社東芝 | ホログラム記録媒体およびその製造方法 |
| JP5028844B2 (ja) * | 2006-04-14 | 2012-09-19 | Ｄｉｃ株式会社 | エポキシ樹脂組成物、その硬化物、新規エポキシ化合物及びこの製造方法 |
| WO2010093970A2 (en) * | 2009-02-13 | 2010-08-19 | Monsanto Technology Llc | Encapsulation of herbicides to reduce crop injury |
| JP5562267B2 (ja) * | 2010-02-08 | 2014-07-30 | 旭化成ケミカルズ株式会社 | ブロックポリイソシアネート組成物及びこれを含む塗料組成物 |
| CN102753596B (zh) | 2010-02-08 | 2014-03-26 | 旭化成化学株式会社 | 封闭多异氰酸酯组合物和含有其的涂料组合物 |
| JP5572567B2 (ja) * | 2010-02-08 | 2014-08-13 | 旭化成ケミカルズ株式会社 | ブロックポリイソシアネート組成物を製造する方法 |
| JP5572566B2 (ja) * | 2010-02-08 | 2014-08-13 | 旭化成ケミカルズ株式会社 | ブロックポリイソシアネート組成物及びこれを含む塗料組成物 |
| JP5572565B2 (ja) * | 2010-02-08 | 2014-08-13 | 旭化成ケミカルズ株式会社 | ブロックポリイソシアネート組成物を製造する方法 |
| JP5562271B2 (ja) * | 2010-06-04 | 2014-07-30 | 旭化成ケミカルズ株式会社 | ブロックポリイソシアネート組成物の製造方法 |
| AU2011291580B2 (en) | 2010-08-18 | 2015-08-20 | Monsanto Technology Llc | Early applications of encapsulated acetamides for reduced injury in crops |
| EP2785762A2 (en) | 2011-12-01 | 2014-10-08 | Dow Global Technologies LLC | Liquid accelerator composition for hardeners |
| MX383040B (es) | 2014-01-27 | 2025-03-13 | Monsanto Technology Llc | Concentrados herbicidas acuosos. |
| CA3066746A1 (en) | 2017-06-13 | 2018-12-20 | Monsanto Technology Llc | Microencapsulated herbicides |
| PY2005101A (es) | 2019-01-30 | 2021-01-08 | Monsanto Tech | Herbicidas de acetamida microencapsulada |
| WO2023104849A1 (en) | 2021-12-08 | 2023-06-15 | Ferro Gmbh | Environmentally friendly medium for ceramic colours for indirect decoration of glass, porcelain, bone china, enamel, and ceramics |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2174239A (en) * | 1936-03-05 | 1939-09-26 | Standard Oil Dev Co | Preparing acetyl acetic acid derivatives |
| US2152132A (en) * | 1936-12-12 | 1939-03-28 | Carbide & Carbon Chem Corp | Acetoacetyl amides and process for their preparation |
| US2325567A (en) * | 1941-04-09 | 1943-07-27 | Rohm & Haas | N-polyalkylene polyaminomalonamide |
| FR900605A (fr) * | 1943-10-15 | 1945-07-04 | Geigy Ag J R | Diamides substituées dérivant d'acides alcoylène-dicarboxyliques et leurs procédés de préparation |
| JPS5137959B2 (sv) * | 1974-05-30 | 1976-10-19 | ||
| US4036985A (en) * | 1975-07-16 | 1977-07-19 | Jose Amato | Mono substituted malonic acid diamides and process of preparing them |
| DE2640295C3 (de) * | 1976-09-08 | 1979-06-13 | Hoechst Ag, 6000 Frankfurt | Einbrennlacke auf der Grundlage von freie Hydroxylgruppen enthaltenden PoIyepoxidverbindungen und blockierten Polyisocyanaten |
| US4439593A (en) * | 1983-05-26 | 1984-03-27 | Mobay Chemical Corporation | Polyurethane compositions with improved storage stability |
| AT381500B (de) * | 1985-05-29 | 1986-10-27 | Vianova Kunstharz Ag | Verfahren zur herstellung von vernetzungskomponenten und deren verwendung fuer lackbindemittel |
-
1987
- 1987-04-09 DE DE19873711947 patent/DE3711947A1/de not_active Withdrawn
-
1988
- 1988-04-02 DE DE88105356T patent/DE3887702D1/de not_active Expired - Lifetime
- 1988-04-02 AT AT88105356T patent/ATE101403T1/de not_active IP Right Cessation
- 1988-04-02 EP EP88105356A patent/EP0286933B1/de not_active Expired - Lifetime
- 1988-04-02 ES ES88105356T patent/ES2061538T3/es not_active Expired - Lifetime
- 1988-04-07 FI FI881615A patent/FI97145C/sv not_active IP Right Cessation
- 1988-04-07 US US07/178,476 patent/US4859788A/en not_active Expired - Fee Related
- 1988-04-08 ZA ZA882444A patent/ZA882444B/xx unknown
- 1988-04-08 JP JP63085560A patent/JP2610644B2/ja not_active Expired - Lifetime
- 1988-04-08 NO NO881546A patent/NO171683C/no not_active IP Right Cessation
- 1988-04-08 AU AU14417/88A patent/AU601833B2/en not_active Ceased
- 1988-04-08 DK DK193188A patent/DK193188A/da not_active Application Discontinuation
- 1988-04-08 IE IE105588A patent/IE61573B1/en not_active IP Right Cessation
- 1988-04-08 CA CA000563622A patent/CA1340337C/en not_active Expired - Fee Related
- 1988-04-08 PT PT87200A patent/PT87200B/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FI97145C (sv) | 1996-10-25 |
| EP0286933A2 (de) | 1988-10-19 |
| ZA882444B (en) | 1988-09-29 |
| US4859788A (en) | 1989-08-22 |
| ES2061538T3 (es) | 1994-12-16 |
| IE61573B1 (en) | 1994-11-16 |
| AU601833B2 (en) | 1990-09-20 |
| CA1340337C (en) | 1999-01-26 |
| NO881546L (no) | 1988-10-10 |
| DK193188A (da) | 1988-10-10 |
| DE3711947A1 (de) | 1988-10-20 |
| DE3887702D1 (de) | 1994-03-24 |
| JPS63265916A (ja) | 1988-11-02 |
| NO171683C (no) | 1993-04-21 |
| IE881055L (en) | 1988-10-09 |
| NO881546D0 (no) | 1988-04-08 |
| PT87200A (pt) | 1988-05-01 |
| DK193188D0 (da) | 1988-04-08 |
| PT87200B (pt) | 1992-07-31 |
| FI881615A0 (sv) | 1988-04-07 |
| FI881615L (sv) | 1988-10-10 |
| EP0286933A3 (en) | 1989-07-19 |
| ATE101403T1 (de) | 1994-02-15 |
| AU1441788A (en) | 1988-10-13 |
| JP2610644B2 (ja) | 1997-05-14 |
| NO171683B (no) | 1993-01-11 |
| EP0286933B1 (de) | 1994-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB | Publication of examined application | ||
| MM | Patent lapsed |
Owner name: HOECHST AKTIENGESELLSCHAFT |