JP2017533328A - 高温適用のための向上させたゲル化時間を有するアミドポリアミン - Google Patents
高温適用のための向上させたゲル化時間を有するアミドポリアミン Download PDFInfo
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- JP2017533328A JP2017533328A JP2017523970A JP2017523970A JP2017533328A JP 2017533328 A JP2017533328 A JP 2017533328A JP 2017523970 A JP2017523970 A JP 2017523970A JP 2017523970 A JP2017523970 A JP 2017523970A JP 2017533328 A JP2017533328 A JP 2017533328A
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- polyamine
- aminopropyl
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 44
- 229920000768 polyamine Polymers 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 229920000647 polyepoxide Polymers 0.000 claims description 15
- 150000001735 carboxylic acids Chemical class 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims description 13
- 150000002118 epoxides Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 238000000576 coating method Methods 0.000 claims description 10
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical group C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims description 10
- 239000003784 tall oil Substances 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 7
- ZAXCZCOUDLENMH-UHFFFAOYSA-N 3,3,3-tetramine Chemical compound NCCCNCCCNCCCN ZAXCZCOUDLENMH-UHFFFAOYSA-N 0.000 claims description 6
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 6
- 229920002873 Polyethylenimine Polymers 0.000 claims description 5
- 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 claims description 5
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 claims description 5
- -1 amide amine Chemical class 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 3
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 3
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 claims description 3
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- OTBHHUPVCYLGQO-UHFFFAOYSA-N bis(3-aminopropyl)amine Chemical compound NCCCNCCCN OTBHHUPVCYLGQO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims description 3
- YCSRPJMGDRNYCY-UHFFFAOYSA-N n'-[2-[bis(3-aminopropyl)amino]ethyl]propane-1,3-diamine Chemical compound NCCCNCCN(CCCN)CCCN YCSRPJMGDRNYCY-UHFFFAOYSA-N 0.000 claims description 3
- XVQKINPUNPALRP-UHFFFAOYSA-N n'-[3-[bis(3-aminopropyl)amino]propyl]propane-1,3-diamine Chemical compound NCCCNCCCN(CCCN)CCCN XVQKINPUNPALRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000466 oxiranyl group Chemical group 0.000 claims description 3
- 229920000333 poly(propyleneimine) Polymers 0.000 claims description 3
- 239000004848 polyfunctional curative Substances 0.000 claims description 3
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 3
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical group C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims 1
- 239000004593 Epoxy Substances 0.000 abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 14
- 239000003822 epoxy resin Substances 0.000 description 13
- CZRCFAOMWRAFIC-UHFFFAOYSA-N 5-(tetradecyloxy)-2-furoic acid Chemical compound CCCCCCCCCCCCCCOC1=CC=C(C(O)=O)O1 CZRCFAOMWRAFIC-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000001408 amides Chemical class 0.000 description 9
- 229920003986 novolac Polymers 0.000 description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 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 4
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000007655 standard test method Methods 0.000 description 3
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- 229930185605 Bisphenol Natural products 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000463 material Substances 0.000 description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- LMVLMHGTZULBRX-UHFFFAOYSA-N 2-[2,2,2-tris(2-hydroxyphenyl)ethyl]phenol Chemical compound OC1=CC=CC=C1CC(C=1C(=CC=CC=1)O)(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LMVLMHGTZULBRX-UHFFFAOYSA-N 0.000 description 1
- LJBWJFWNFUKAGS-UHFFFAOYSA-N 2-[bis(2-hydroxyphenyl)methyl]phenol Chemical compound OC1=CC=CC=C1C(C=1C(=CC=CC=1)O)C1=CC=CC=C1O LJBWJFWNFUKAGS-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
- MEEKGULDSDXFCN-UHFFFAOYSA-N 2-pentylphenol Chemical compound CCCCCC1=CC=CC=C1O MEEKGULDSDXFCN-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 description 1
- XRBNDLYHPCVYGC-UHFFFAOYSA-N 4-phenylbenzene-1,2,3-triol Chemical group OC1=C(O)C(O)=CC=C1C1=CC=CC=C1 XRBNDLYHPCVYGC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 0 C*(C)(N*)NC(*)=O Chemical compound C*(C)(N*)NC(*)=O 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/54—Amino amides>
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- 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
- C08G59/20—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 epoxy compounds used
- C08G59/22—Di-epoxy compounds
-
- 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
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- 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)
Abstract
Description
本発明は、エポキシ硬化剤、特にアミドポリアミンを含有するエポキシ硬化剤に関する。
本発明は、比較的低い温度で硬化し、改善されたポットライフを有する硬化剤を提供することによって、従来のアミドアミン硬化剤に係る問題を解決するものである。
(A)分子内に、オキシラン構造の少なくとも2個のエポキシド基を有する、少なくとも1種のフェニルグリシジルエーテルポリエポキシドを含有するエポキシド成分、
(B)1モル当量のポリアミンと、1.15〜1.30モル当量のトール油脂肪酸とを反応させることによって得られる、ポリアミンとトール油脂肪酸とのアミドアミンを含有する硬化剤成分
を含有するエポキシド系組成物に関する。
以下の定義を本明細書で用いる:
「硬化」とは、ポリマー鎖の架橋によってエポキシ樹脂を強化又は硬くすること(アミン、チオール、カルボン酸、アルコール、及びカルボン酸無水物などの硬化剤によって起こる)を意味し、粘度計を用いて、経時的な粘度の増加によって測定される。
を有する。
本発明の特定の態様を説明するために以下の実施例を提供するが、これらは、本明細書に添付された請求項の範囲を制限するものではない。これらの実施例は、TOFAとDETAとのアミドアミンの比較であり、DETA対TOFAの比が1:1.15〜1:1.30である場合、潜在性又はゲル化時間(20,000cPまでの粘度増加により測定)が、1:1のモル比を有するDETA対TOFAから製造する場合よりも2〜3倍増加することを表す。TETA及びTOFAから製造されたアミドアミンによっても同様の結果が得られた。さらに、硬化の速度(65℃で完全な硬度を発現するための時間により測定)は、実質的に変化しなかった。
ポリアミンと0.15モル過剰のTOFAからアミドアミンを製造する手順
ジエチレントリアミン(DETA)(供給元;Air Products社)を含有するポリアミン(1.0モル)を、熱電対、窒素吸入口、及び冷却器を備える反応釜に装入した。そして、ポリアミンをトール油脂肪酸(1.15モル、供給元;Air Products社)で処理した。この混合物を225℃に加熱し、水が完全に留去されるまでこの温度で保持した。この混合物を室温に冷却した。
ポリアミンと0.30モル過剰のTOFAからアミドアミンを製造する手順
ジエチレントリアミン(DETA)(供給元;Air Products社)を含有するポリアミン(1.0モル)を、熱電対、窒素吸入口、及び冷却器を備える反応釜に装入した。そして、ポリアミンをトール油脂肪酸(1.30モル)で処理した。この混合物を225℃に加熱し、水が完全に留去されるまでこの温度で保持した。この混合物を室温に冷却した。
実施例1の硬化剤(そのアミン水素当量(AHEW)により決定された量)を、100gのビスフェノールAジグリシジルエーテル(EPON(登録商標)828エポキシ)と、スパチュラを用いて、200mLのガラスジャー中で混合する。前記混合物15gを、ディスポーザブル型アルミニウム製容器(Brookfield社のHT−2DB)に移す。ディスポーザブル型アルミニウム製スピンドル(Brookfield社のSC4−27D)を、硬化剤混合物を有する容器に入れ、粘度計(Brookfield社のRVDV−II+Pro)を起動して、1分間に1つの速度でデータポイントを収集する。ポットライフは、25℃で20,000cPに達するまでの時間(h)として記録する。完全な硬化は、目視、及び触感による硬度によって特定する。表1に試験結果をまとめる。
Claims (12)
- エポキシド系組成物であって、
(A)分子内において、オキシラン構造の少なくとも2個のエポキシド基を有する、少なくとも1種のフェニルグリシジルエーテルポリエポキシドを含有するエポキシド成分、及び
(B)1モル当量のポリアミンと、1.15〜1.30モル当量のトール油脂肪酸とを反応させることによって得られる、ポリアミンとトール油脂肪酸とのアミドアミンを含有する硬化剤成分
を含有する前記組成物。 - 請求項1に記載の組成物であって、エポキシド成分と硬化剤成分を組み合わせた後、約11時間〜約30時間以内において、約20,000cP未満の粘度を有する前記組成物。
- 請求項1に記載の組成物であって、約60℃〜約100℃の間の硬化温度を有する前記組成物。
- 少なくとも1種のカルボン酸と、少なくとも1種のポリアミンとを反応させることを含む、硬化剤を製造するための方法。
- 請求項4に記載の方法であって、ポリアミンに対して約0.15モル〜約0.30モル過剰のカルボン酸を190℃超の温度で反応させる前記方法。
- 請求項4に記載の方法であって、カルボン酸が、オクタン酸、2−エチルヘキサン酸、デカン酸、ドデカン酸、及びトール油脂肪酸、及びダイマー脂肪酸から成る群より選択される少なくとも1種を含む前記方法。
- 請求項4に記載の方法であって、ポリアミンが、ポリエチレンアミン、ジプロピレントリアミン、ポリプロピレンアミン、N−3−アミノプロピルエチレンジアミン、アミノプロピル化エチレンジアミン、アミノプロピル化プロピレンジアミン、1,6−ヘキサンジアミン、3,3,5−トリメチル−1,6−ヘキサンジアミン、トリプロピレンテトラミン、N−3−アミノプロピル−1,3−ジアミノプロパン、N,N’−ビス(3−アミノプロピル)−1,3−ジアミノプロパン、N,N,N’−トリス(3−アミノプロピル)−1,3−ジアミノプロパン、2−メチル−1,5−ペンタンジアミン、N,N’−ビス(3−アミノプロピル)エチレンジアミン(N4)、N,N,N’−トリス(3−アミノプロピル)エチレンジアミン(N5)、及びこれらの任意の組み合わせから成る群より選択される少なくとも1種を含む前記方法。
- 請求項1に記載の組成物であって、硬化剤が、請求項4の方法によって製造される前記組成物。
- 被覆を作製するための、請求項1に記載の組成物の使用。
- 請求項10に記載の使用であって、被覆が、パイプラインの内部に適用される前記使用。
- 請求項10に記載の使用であって、被覆が、約80部の硬化剤に対して約100部の樹脂を含む前記使用。
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KR20200109790A (ko) * | 2019-03-14 | 2020-09-23 | 주식회사 케이씨씨 | 아민-아마이드 수지 조성물 및 이의 제조 방법 |
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WO2016073564A1 (en) | 2016-05-12 |
KR102532938B1 (ko) | 2023-05-16 |
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US20160122467A1 (en) | 2016-05-05 |
JP6720164B2 (ja) | 2020-07-08 |
KR20220016280A (ko) | 2022-02-08 |
US10174154B2 (en) | 2019-01-08 |
CA2966520A1 (en) | 2016-05-12 |
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KR20170078797A (ko) | 2017-07-07 |
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