KR101590981B1 - 벤질화된 폴리아민 경화제 - Google Patents
벤질화된 폴리아민 경화제 Download PDFInfo
- Publication number
- KR101590981B1 KR101590981B1 KR1020147010875A KR20147010875A KR101590981B1 KR 101590981 B1 KR101590981 B1 KR 101590981B1 KR 1020147010875 A KR1020147010875 A KR 1020147010875A KR 20147010875 A KR20147010875 A KR 20147010875A KR 101590981 B1 KR101590981 B1 KR 101590981B1
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- benzylated
- benzyl
- benzaldehyde
- amine
- 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.)
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- 229920000768 polyamine Polymers 0.000 title claims abstract description 102
- 239000000203 mixture Substances 0.000 claims abstract description 131
- -1 benzaldehyde compound Chemical class 0.000 claims abstract description 81
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 66
- 239000004593 Epoxy Substances 0.000 claims abstract description 56
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 51
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 15
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 13
- 125000004956 cyclohexylene group Chemical group 0.000 claims abstract description 11
- 150000001412 amines Chemical class 0.000 claims description 62
- 239000000047 product Substances 0.000 claims description 44
- 239000003822 epoxy resin Substances 0.000 claims description 38
- 229920000647 polyepoxide Polymers 0.000 claims description 38
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 37
- 238000000576 coating method Methods 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 19
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- 239000000853 adhesive Substances 0.000 claims description 16
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- 239000000376 reactant Substances 0.000 claims description 14
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 9
- 238000009408 flooring Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 150000003935 benzaldehydes Chemical class 0.000 claims description 7
- 239000000565 sealant Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 238000010276 construction Methods 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- GKXVJHDEWHKBFH-UHFFFAOYSA-N xylylenediamine group Chemical group C=1(C(=CC=CC1)CN)CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims description 6
- BDYVWDMHYNGVGE-UHFFFAOYSA-N [2-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCCC1CN BDYVWDMHYNGVGE-UHFFFAOYSA-N 0.000 claims description 5
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical class NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 claims description 5
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 claims description 4
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 3
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 3
- 229940073608 benzyl chloride Drugs 0.000 claims description 3
- MBXXQYJBFRRFCK-UHFFFAOYSA-N benzyl fluoride Chemical compound FCC1=CC=CC=C1 MBXXQYJBFRRFCK-UHFFFAOYSA-N 0.000 claims description 3
- FIRQYUPQXNPTKO-UHFFFAOYSA-N ctk0i2755 Chemical class N[SiH2]N FIRQYUPQXNPTKO-UHFFFAOYSA-N 0.000 claims description 3
- XJTQJERLRPWUGL-UHFFFAOYSA-N iodomethylbenzene Chemical compound ICC1=CC=CC=C1 XJTQJERLRPWUGL-UHFFFAOYSA-N 0.000 claims description 3
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
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- 238000006243 chemical reaction Methods 0.000 description 21
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 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 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 description 16
- 239000000463 material Substances 0.000 description 16
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 14
- 238000005574 benzylation reaction Methods 0.000 description 14
- WTFAGPBUAGFMQX-UHFFFAOYSA-N 1-[2-[2-(2-aminopropoxy)propoxy]propoxy]propan-2-amine Chemical compound CC(N)COCC(C)OCC(C)OCC(C)N WTFAGPBUAGFMQX-UHFFFAOYSA-N 0.000 description 13
- 238000004519 manufacturing process Methods 0.000 description 13
- 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 12
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 229940106691 bisphenol a Drugs 0.000 description 7
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 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
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 150000002989 phenols Chemical class 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
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- 238000006268 reductive amination reaction Methods 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
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- XYXBMCIMPXOBLB-UHFFFAOYSA-N 3,4,5-tris(dimethylamino)-2-methylphenol Chemical compound CN(C)C1=CC(O)=C(C)C(N(C)C)=C1N(C)C XYXBMCIMPXOBLB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 3
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- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 2
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- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- XZAHJRZBUWYCBM-UHFFFAOYSA-N [1-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1(CN)CCCCC1 XZAHJRZBUWYCBM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- PTFIPECGHSYQNR-UHFFFAOYSA-N cardanol Natural products CCCCCCCCCCCCCCCC1=CC=CC(O)=C1 PTFIPECGHSYQNR-UHFFFAOYSA-N 0.000 description 1
- 235000020226 cashew nut Nutrition 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000010960 cold rolled steel Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- AXEYWFGSQDLHDX-UHFFFAOYSA-N hexane-1,3,6-triamine Chemical compound NCCCC(N)CCN AXEYWFGSQDLHDX-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000333 poly(propyleneimine) Polymers 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 238000005891 transamination reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Natural products NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13/242,153 US8729213B2 (en) | 2011-09-23 | 2011-09-23 | Benzylated polyamine curing agents |
| US13/242,153 | 2011-09-23 | ||
| PCT/US2012/039234 WO2013043241A1 (en) | 2011-09-23 | 2012-05-24 | Benzylated polyamine curing agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140082724A KR20140082724A (ko) | 2014-07-02 |
| KR101590981B1 true KR101590981B1 (ko) | 2016-02-02 |
Family
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013161481A1 (ja) * | 2012-04-27 | 2013-10-31 | 三菱瓦斯化学株式会社 | エポキシ樹脂硬化剤、エポキシ樹脂組成物、及びガスバリア性接着剤、並びにガスバリア性積層体 |
| US10626290B2 (en) * | 2013-12-16 | 2020-04-21 | Ppg Industries Ohio, Inc. | Method of extending pot life of coating compositions |
| CN106471421B (zh) * | 2014-07-03 | 2019-07-09 | 3M创新有限公司 | 具有减小的边缘侵入和改善的颜色稳定性的量子点制品 |
| US20170260322A1 (en) | 2014-09-22 | 2017-09-14 | Evonik Degussa Gmbh | Ketimines of benzylated polyamines as curing agents |
| JP6565229B2 (ja) * | 2015-03-06 | 2019-08-28 | 東ソー株式会社 | エポキシ樹脂用硬化剤 |
| CN107428675A (zh) * | 2015-03-11 | 2017-12-01 | 三菱瓦斯化学株式会社 | 新型多胺化合物及其制造方法，以及使用其的环氧树脂用固化剂、环氧树脂组合物和环氧树脂固化物 |
| RU2725889C2 (ru) | 2015-03-23 | 2020-07-07 | Сикэ Текнолоджи Аг | Праймер или адгезив на основе эпоксидной смолы холодного отверждения |
| EP3205681A1 (de) * | 2016-02-15 | 2017-08-16 | Sika Technology AG | Härtbare zusammensetzung |
| EP3375803A1 (de) | 2017-03-14 | 2018-09-19 | Sika Technology Ag | Härter für emissionsarme epoxidharz-zusammensetzungen |
| US10774292B2 (en) | 2017-05-11 | 2020-09-15 | Ecolab Usa Inc. | Compositions and method for floor cleaning or restoration |
| CN107501524B (zh) * | 2017-08-30 | 2020-05-12 | 本源精化环保科技有限公司 | N,n’烷基化二氨基二苯基甲烷类固化剂及制备方法 |
| JP6939365B2 (ja) * | 2017-10-03 | 2021-09-22 | 三菱瓦斯化学株式会社 | アミン組成物の製造方法 |
| JP2021502455A (ja) * | 2017-11-09 | 2021-01-28 | エボニック オペレーションズ ゲーエムベーハー | ベンジル化トリアミノノナンおよびその使用 |
| CN108410406A (zh) * | 2018-03-12 | 2018-08-17 | 常州五荣化工有限公司 | 一种改性环氧树脂灌封胶的制备方法 |
| CN109401582A (zh) * | 2018-09-10 | 2019-03-01 | 张程玙 | 水利工程挡土墙用防水涂料及其制备方法 |
| EP3677648A1 (en) * | 2019-01-03 | 2020-07-08 | Sika Technology Ag | Process for detecting wear in floor coating systems and compositions thereof |
| CN109852314B (zh) * | 2019-03-11 | 2021-01-05 | 上海域金澜优实业有限公司 | 一种耐白化美缝剂 |
| CN109897568B (zh) * | 2019-03-11 | 2020-11-24 | 上海域金澜优实业有限公司 | 一种美缝剂用耐白化固化剂及其制备方法 |
| KR102298818B1 (ko) * | 2019-07-16 | 2021-09-07 | 주식회사 볼빅 | 폴리우레탄 제조용 조성물 |
| US20230068858A1 (en) * | 2020-02-24 | 2023-03-02 | Sika Technology Ag | Amine epoxy resin adduct |
| WO2025181188A1 (en) * | 2024-02-27 | 2025-09-04 | Evonik Operations Gmbh | Benzylated polyalkylene polyamines composition with enhanced epoxy coatings performance |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB2045269A (en) * | 1979-03-15 | 1980-10-29 | Zeiss Jena Veb Carl | Thermoplastic Polymers from Diamines and Diepoxides |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE1923062A1 (de) | 1968-05-10 | 1969-11-20 | Meisei Chemical Works Co Ltd | Verfahren zur Verbesserung der Farbechtheit von gefaerbtem Celluloseacetatmaterial |
| US3624671A (en) | 1968-08-23 | 1971-11-30 | Pellicer Carlos F | Reinforced plastic tubing |
| US3634316A (en) | 1968-08-23 | 1972-01-11 | Showa Denko Kk | Sulfur-vulcanizable natural and synthetic rubbery polymers containing xylylene diamines as antiozonants |
| JPS5245773B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-02-12 | 1977-11-18 | ||
| JPS4917418A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1972-06-05 | 1974-02-15 | ||
| JPS5245773A (en) * | 1975-10-09 | 1977-04-11 | Dai Tekkosho:Kk | Cloth fitting/removing mechanism in dewatering apparatus |
| JPS605938B2 (ja) * | 1979-01-27 | 1985-02-14 | 三菱製紙株式会社 | 有機電子写真感光体の製造方法 |
| US4308085A (en) | 1980-07-28 | 1981-12-29 | Jenoptik Jena Gmbh | Process for the preparation of high molecular thermoplastic epoxide-amine-polyadducts |
| IN166475B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1985-12-12 | 1990-05-19 | Council Scient Ind Res | |
| JPS63172721A (ja) * | 1987-01-10 | 1988-07-16 | Minoru Sugisawa | ホルムアルデヒド重縮合物硬化反応エポキシ樹脂に水を混合したバインダ−に多量の無機系微粉を混合し常温硬化により整形後、加熱によるバインダ−樹脂の炭素結合を行う方法 |
| US5208959A (en) | 1991-05-10 | 1993-05-11 | Huck Patents, Inc. | Offset nose assembly with pin releasing assembly for fastener installation tools |
| US5280091A (en) | 1992-02-07 | 1994-01-18 | Air Products And Chemicals, Inc. | Epoxy resins cured with mixed methylene bridged poly(cyclohexyl-aromatic)amine curing agents |
| GB2364305A (en) | 2000-07-03 | 2002-01-23 | Secr Defence | Redox-active self assembled metallomacrocycles |
| US7396902B2 (en) | 2003-02-13 | 2008-07-08 | Mitsubishi Gas Chemical Company, Inc. | Epoxy resin curing agent of aliphatic diamine/styrene addition product |
| CN1966601A (zh) * | 2005-11-17 | 2007-05-23 | 中国科学院兰州化学物理研究所 | 一种高温抗振防腐蚀密封剂 |
| JP4917418B2 (ja) | 2006-12-14 | 2012-04-18 | タイコエレクトロニクスジャパン合同会社 | 端子挿入装置 |
| US8147964B2 (en) | 2007-02-07 | 2012-04-03 | Air Products And Chemicals, Inc. | Benzylated polyalkylene polyamines and uses thereof |
| US8518547B2 (en) | 2007-02-07 | 2013-08-27 | Air Products And Chemicals, Inc. | Alkylated polyalkylene polyamines and uses thereof |
| US8168296B2 (en) * | 2007-02-07 | 2012-05-01 | Air Products And Chemicals, Inc. | Benzylated polyalkylene polyamines and uses thereof |
| US8318309B2 (en) | 2007-02-07 | 2012-11-27 | Air Products And Chemicals, Inc. | Benzylated aminopropylated alkylenediamines and uses thereof |
| CN102061011B (zh) * | 2010-12-17 | 2012-08-08 | 无锡阿科力化工有限公司 | 插层剂及其制备方法 |
| CN102061061B (zh) * | 2010-12-17 | 2012-02-22 | 无锡阿科力化工有限公司 | 剥离型蒙脱土和环氧树脂复合材料的制备方法 |
| EP2546230A1 (de) * | 2011-07-15 | 2013-01-16 | Sika Technology AG | Emissionsarmer Härter für Epoxidharze |
-
2011
- 2011-09-23 US US13/242,153 patent/US8729213B2/en active Active
-
2012
- 2012-05-24 EP EP12726527.0A patent/EP2758446B1/en active Active
- 2012-05-24 KR KR1020147010875A patent/KR101590981B1/ko active Active
- 2012-05-24 IN IN2907CHN2014 patent/IN2014CN02907A/en unknown
- 2012-05-24 WO PCT/US2012/039234 patent/WO2013043241A1/en active Application Filing
- 2012-05-24 JP JP2014531807A patent/JP5969612B2/ja active Active
- 2012-05-24 ES ES12726527.0T patent/ES2637367T3/es active Active
- 2012-05-24 CN CN201280045841.3A patent/CN103814057B/zh active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2045269A (en) * | 1979-03-15 | 1980-10-29 | Zeiss Jena Veb Carl | Thermoplastic Polymers from Diamines and Diepoxides |
Also Published As
| Publication number | Publication date |
|---|---|
| JP5969612B2 (ja) | 2016-08-17 |
| JP2014531496A (ja) | 2014-11-27 |
| EP2758446A1 (en) | 2014-07-30 |
| ES2637367T3 (es) | 2017-10-13 |
| EP2758446B1 (en) | 2017-07-05 |
| CN103814057A (zh) | 2014-05-21 |
| WO2013043241A1 (en) | 2013-03-28 |
| KR20140082724A (ko) | 2014-07-02 |
| US20130079435A1 (en) | 2013-03-28 |
| US8729213B2 (en) | 2014-05-20 |
| IN2014CN02907A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-07-03 |
| CN103814057B (zh) | 2016-08-17 |
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