JP2016503113A - 低放出性エポキシ樹脂製品用の硬化剤 - Google Patents
低放出性エポキシ樹脂製品用の硬化剤 Download PDFInfo
- Publication number
- JP2016503113A JP2016503113A JP2015551164A JP2015551164A JP2016503113A JP 2016503113 A JP2016503113 A JP 2016503113A JP 2015551164 A JP2015551164 A JP 2015551164A JP 2015551164 A JP2015551164 A JP 2015551164A JP 2016503113 A JP2016503113 A JP 2016503113A
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- Prior art keywords
- bis
- curing agent
- epoxy resin
- aminomethyl
- adduct
- 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.)
- Granted
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 89
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 86
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 75
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims abstract description 30
- CUFXMPWHOWYNSO-UHFFFAOYSA-N 2-[(4-methylphenoxy)methyl]oxirane Chemical compound C1=CC(C)=CC=C1OCC1OC1 CUFXMPWHOWYNSO-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000203 mixture Substances 0.000 claims description 51
- 150000001412 amines Chemical class 0.000 claims description 46
- 229920000768 polyamine Polymers 0.000 claims description 44
- -1 2-ethylhexyl Chemical group 0.000 claims description 28
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 22
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 20
- 125000003700 epoxy group Chemical group 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 11
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 claims description 7
- 125000001033 ether group Chemical group 0.000 claims description 7
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 claims description 6
- 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 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 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 5
- 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 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 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 claims description 3
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical group NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 claims description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 2
- IGSBHTZEJMPDSZ-UHFFFAOYSA-N 4-[(4-amino-3-methylcyclohexyl)methyl]-2-methylcyclohexan-1-amine Chemical compound C1CC(N)C(C)CC1CC1CC(C)C(N)CC1 IGSBHTZEJMPDSZ-UHFFFAOYSA-N 0.000 claims description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 2
- GMTFURRRXIRGLH-UHFFFAOYSA-N C12CCCC2C2(CN)CC1CC2 Chemical compound C12CCCC2C2(CN)CC1CC2 GMTFURRRXIRGLH-UHFFFAOYSA-N 0.000 claims description 2
- DPNYVVLIXCRDQZ-UHFFFAOYSA-N [5-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine [6-(aminomethyl)-2-bicyclo[2.2.1]heptanyl]methanamine Chemical compound NCC1CC2CC1CC2CN.NCC1CC2CC(CN)C1C2 DPNYVVLIXCRDQZ-UHFFFAOYSA-N 0.000 claims description 2
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 claims description 2
- AVKNGPAMCBSNSO-UHFFFAOYSA-N cyclohexylmethanamine Chemical compound NCC1CCCCC1 AVKNGPAMCBSNSO-UHFFFAOYSA-N 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 27
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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 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 description 17
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-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
- 239000010410 layer Substances 0.000 description 13
- 229920003319 Araldite® Polymers 0.000 description 12
- 150000004985 diamines Chemical class 0.000 description 12
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 239000000853 adhesive Substances 0.000 description 7
- 230000001070 adhesive effect Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
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- 239000007789 gas Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
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- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 5
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- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 4
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- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- NMWCVZCSJHJYFW-UHFFFAOYSA-M sodium;3,5-dichloro-2-hydroxybenzenesulfonate Chemical compound [Na+].OC1=C(Cl)C=C(Cl)C=C1S([O-])(=O)=O NMWCVZCSJHJYFW-UHFFFAOYSA-M 0.000 description 1
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- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical class C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 1
- YQKGJRGUAQVYNL-UHFFFAOYSA-N tris(1,2-dichloropropan-2-yl) phosphate Chemical compound ClCC(Cl)(C)OP(=O)(OC(C)(Cl)CCl)OC(C)(Cl)CCl YQKGJRGUAQVYNL-UHFFFAOYSA-N 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- HQUQLFOMPYWACS-UHFFFAOYSA-N tris(2-chloroethyl) phosphate Chemical compound ClCCOP(=O)(OCCCl)OCCCl HQUQLFOMPYWACS-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 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
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/182—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents
- C08G59/184—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing using pre-adducts of epoxy compounds with curing agents with amines
-
- 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
- C08G59/5006—Amines aliphatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Abstract
Description
R1は、その2つの第一級アミノ基を除去した後のTMDの二官能性残基を表し、
R2は、そのエポキシ基を除去した後のクレシルグリシジルエーテルの残基を表す。
脂肪族、脂環式又はアリール脂肪族第一級ジアミン、特に2,2−ジメチル−1,3−プロパンジアミン、1,3−ペンタンジアミン(DAMP)、1,5−ペンタンジアミン、1,5−ジアミノ−2−メチルペンタン(MPMD)、2−ブチル−2−エチル−1,5−ペンタンジアミン(C11−ネオジアミン)、1,6−ヘキサンジアミン、2,5−ジメチル−1,6−ヘキサンジアミン、2,2,4−及び2,4,4−トリメチルヘキサメチレンジアミン、1,7−ヘプタンジアミン、1,8−オクタンジアミン、1,9−ノナンジアミン、1,10−デカンジアミン、1,11−ウンデカンジアミン、1,12−ドデカンジアミン、1,2−、1,3−及び1,4−ジアミノシクロヘキサン、ビス(4−アミノシクロヘキシル)メタン、ビス(4−アミノ−3−メチルシクロヘキシル)メタン、ビス(4−アミノ−3−エチルシクロヘキシル)メタン、ビス(4−アミノ−3,5−ジメチルシクロヘキシル)メタン、ビス(4−アミノ−3−エチル−5−メチルシクロヘキシル)メタン、1−アミノ−3−アミノメチル−3,5,5−トリメチルシクロヘキサン(=イソホロンジアミン又はIPD)、2−及び4−メチル−1,3−ジアミノシクロヘキサン及びそれらの混合物、1,3−ビス(アミノメチル)シクロヘキサン、1,4−ビス(アミノメチル)シクロヘキサン、2,5(2,6)−ビス(アミノメチル)−ビシクロ[2.2.1]ヘプタン(NBDA)、3(4),8(9)−ビス(アミノメチル)トリシクロ[5.2.1.02,6]−デカン(TCD−ジアミン)、1,4−ジアミノ−2,2,6−トリメチルシクロヘキサン(TMCDA)、1,8−メンタンジアミン、3,9−ビス(3−アミノプロピル)−2,4,8,10−テトラオキサスピロ[5.5]ウンデカン及び1,3−ビス(アミノメチル)ベンゼン(MXDA);
2つ又は3つの第一級脂肪族アミノ基を有する第三級アミノ基含有ポリアミン、特にN,N’−ビス(アミノプロピル)−ピペラジン、N,N−ビス(3−アミノプロピル)メチルアミン、N,N−ビス(3−アミノプロピル)エチルアミン、N,N−ビス(3−アミノプロピル)プロピルアミン、N,N−ビス(3−アミノプロピル)シクロヘキシルアミン、N,N−ビス(3−アミノプロピル)−2−エチル−ヘキシルアミン、トリス(2−アミノエチル)アミン、トリス(2−アミノプロピル)−アミン、トリス(3−アミノプロピル)アミン、及び天然脂肪酸由来の脂肪アミンの2回のシアノエチル化及び続く還元の生成物、例えば、トリアミーン(Triameen)(登録商標)Y12D及びトリアミーン(Triameen)(登録商標)YT(Akzo Nobel製)として入手可能なN,N−ビス(3−アミノプロピル)ドデシルアミン及びN,N−ビス(3−アミノプロピル)牛脂アルキルアミン;
エーテル基含有脂肪族第一級ポリアミン、特にビス(2−アミノエチル)エーテル、3,6−ジオキサオクタン−1,8−ジアミン、4,7−ジオキサデカン−1,10−ジアミン、4,7−ジオキサデカン−2,9−ジアミン、4,9−ジオキサドデカン−1,12−ジアミン、5,8−ジオキサドデカン−3,10−ジアミン、4,7,10−トリオキサトリデカン−1,13−ジアミン及びこれらのジアミンのより高重合度なオリゴマー、ビス(3−アミノプロピル)ポリテトラヒドロフラン及び他のポリテトラヒドロフランジアミン、1,4−ジメチロールシクロヘキサンのプロポキシ化及び続くアミノ化から生成され、特にジェファミン(Jeffamine)(登録商標)RFD−270(Huntsman製)として入手可能な脂環式エーテル基含有ジアミン、並びにポリオキシアルキレンジオール及びポリオキシアルキレントリオールのアミノ化の通常の生成物であり、また、例えば、ジェファミン(Jeffamine)(登録商標)(Huntsman製)、ポリエーテルアミン(BASF製)又はPC amines(商標)(Nitroil製)の名前で入手可能であるポリオキシアルキレンジアミン又はポリオキシアルキレントリアミン、特にジェファミン(Jeffamine)(登録商標)D−230、ジェファミン(Jeffamine)(登録商標)D−400、ジェファミン(Jeffamine)(登録商標)D−2000、ジェファミン(Jeffamine)(登録商標)D−4000、ジェファミン(Jeffamine)(登録商標)T−403、ジェファミン(Jeffamine)(登録商標)T−3000、ジェファミン(Jeffamine)(登録商標)T−5000、ジェファミン(Jeffamine)(登録商標)EDR−104、ジェファミン(Jeffamine)(登録商標)EDR−148及びジェファミン(Jeffamine)(登録商標)EDR−176、並びにBASF又はNitroil製の対応するアミン;
第二級アミノ基を有する第一級ジアミン、例えば特に3−(2−アミノエチル)アミノプロピルアミン、ビス(ヘキサメチレン)トリアミン(BHMT)、ジエチレントリアミン(DETA)、トリエチレンテトラアミン(TETA)、テトラエチレンペンタアミン(TEPA)、ペンタエチレンヘキサアミン(PEHA)及び直鎖状ポリエチレンアミンの高級同族体、例えば、5個〜7個のエチレンアミンユニットを有するポリエチレンポリアミン(いわゆる「高級(higher)エチレンポリアミン」、HEPA)、ジプロピレントリアミン(DPTA)、N−(2−アミノエチル)−1,3−プロパンジアミン(N3−アミン)、N,N’−ビス(3−アミノプロピル)エチレンジアミン(N4−アミン)、N,N’−ビス(3−アミノプロピル)−1,4−ジアミノブタン、N5−(3−アミノプロピル)−2−メチル−1,5−ペンタンジアミン、N3−(3−アミノペンチル)−1,3−ペンタンジアミン、N5−(3−アミノ−1−エチルプロピル)−2−メチル−1,5−ペンタンジアミン又はN,N’−ビス(3−アミノ−1−エチルプロピル)−2−メチル−1,5−ペンタンジアミン等の少なくとも2つの第一級アミノ基を有する、第一級ジ−及びポリアミンの複数回のシアノエチル化又はシアノブチル化、及び続く水素化の生成物;
1つの第一級アミノ基と少なくとも1つの第二級アミノ基とを含有するポリアミン、例えば特にN−ブチル−1,2−エタンジアミン、N−ヘキシル−1,2−エタンジアミン、N−(2−エチルヘキシル)−1,2−エタンジアミン、N−シクロヘキシル−1,2−エタンジアミン、4−アミノメチル−ピペリジン、N−(2−アミノエチル)ピペラジン、N−メチル−1,3−プロパンジアミン、N−ブチル−1,3−プロパンジアミン、N−(2−エチルヘキシル)−1,3−プロパンジアミン、N−シクロヘキシル−1,3−プロパンジアミン、3−メチルアミノ−1−ペンチルアミン、3−エチルアミノ−1−ペンチルアミン、3−シクロヘキシルアミノ−1−ペンチルアミン、N−ココアルキル−1,3−プロパンジアミン等の脂肪ジアミン、第一級脂肪族ジアミンと、アクリロニトリル、マレイン酸又はフマル酸ジエステル、シトラコン酸ジエステル、アクリル酸及びメタクリル酸エステル、アクリル酸及びメタクリル酸アミド並びにイタコン酸ジエステルとの、1:1のモル比で反応させたマイケル型付加反応の生成物、さらに、第一級ポリアミンと、アルデヒド又はケトンとの部分的還元的アルキル化の生成物、特にこれまでに述べられた2つの第一級アミノ基を有するポリアミン、特に1,6−ヘキサンジアミン、1,5−ジアミノ−2−メチルペンタン、1,3−ビス(アミノメチル)シクロヘキサン、1,4−ビス(アミノメチル)シクロヘキサン、1,3−ビス(アミノメチル)ベンゼン、BHMT、DETA、TETA、TEPA、DPTA、N3−アミン及びN4−アミンのN−モノアルキル化生成物(ここで好ましいアルキル基はベンジル、イソブチル、ヘキシル及び2−エチルヘキシルである)、並びに部分的にスチレン化されたポリアミン、特に市販のガスカミン(Gaskamine)(登録商標)240(三菱ガス化学株式会社製);
第二級ジアミン、例えば特にこれまでに述べられた2つの第一級アミノ基を有するポリアミンのN,N’−ジアルキル化生成物、特に1,6−ヘキサンジアミン、1,5−ジアミノ−2−メチル−ペンタン、1,3−ビス(アミノメチル)シクロヘキサン、1,4−ビス(アミノメチル)−シクロヘキサン、1,3−ビス(アミノメチル)ベンゼン、BHMT、DETA、TETA、TEPA、DPTA、N3−アミン又はN4−アミンのN,N’−ジアルキル化生成物(ここで好ましいアルキル基は2−フェニルエチル、ベンジル、イソブチル、ヘキシル及び2−エチルヘキシルである)。
商標名チオコール(Thiokol)(登録商標)(Morton Thiokol製、例えばSPI Suppliesから又はToray Fine Chemicalsから入手可能)、特にタイプLP−3、LP−33、LP−980、LP−23、LP−55、LP−56、LP−12、LP−31、LP−32及びLP−2として知られている;また商標名チオプラスト(Thioplast)(登録商標)(Akzo Nobel製)、特にタイプG 10、G 112、G 131、G 1、G 12、G 21、G 22、G 44及びG 4として知られている、液状メルカプタン末端ポリスルフィドポリマー;
例えば、ポリオキシアルキルレンジオール及びポリオキシアルキルレントリオールを、エピクロロヒドリン又はアルキレンオキシドと反応させた後に、硫化水素ナトリウムと反応させることによって入手可能なメルカプタン末端ポリオキシアルキルレンエーテル;
商標名キャップキュア(Capcure)(登録商標)(Cognis製)、特にタイプWR−8、LOF及び3−800として知られている、ポリオキシアルキルレン誘導体の形態のメルカプタン末端化合物;
チオカルボン酸のポリエステル、例えば、ペンタエリスリトールテトラメルカプトアセテート、トリメチロールプロパントリメルカプトアセテート、グリコールジメルカプトアセテート、ペンタエリスリトールテトラ−(3−メルカプトプロピオネート)、トリメチロールプロパン−トリ−(3−メルカプトプロピオネート)及びグリコールジ−(3−メルカプトプロピオネート)、並びに、ポリオキシアルキルレンジオール及びポリオキシアルキルレントリオール、エトキシ化トリメチロールプロパン及びポリエステルジオールと、チオグリコール酸及び2−又は3−メルカプトプロピオン酸等のチオカルボン酸とのエステル化生成物;並びに、
付加的なメルカプト基含有化合物、特に2,4,6−トリメルカプト−1,3,5−トリアジン、2,2’−(エチレンジオキシ)−ジエタンチオール(トリエチレングリコールジメルカプタン)及びエタンジチオール等。
ビスフェノールA、ビスフェノールF又はビスフェノールA/F、ここでAはアセトンを表し、Fはホルムアルデヒドを表しており、これらはこれらのビスフェノールの調製用の出発物質として働く。ビスフェノールFの場合、位置異性体も存在することができ、特に2,4’−及び2,2’−ヒドロキシフェニルメタンから誘導することができる;
ジヒドロキシベンゼン誘導体、例えばレゾルシノール、ヒドロキノン及びピロカテコール;
他のビスフェノール又はポリフェノール、例えばビス−(4−ヒドロキシ−3−メチルフェニル)−メタン、2,2−ビス−(4−ヒドロキシ−3−メチルフェニル)−プロパン(ビスフェノールC)、ビス−(3,5−ジメチル−4−ヒドロキシフェニル)−メタン、2,2−ビス−(3,5−ジメチル−4−ヒドロキシフェニル)−プロパン、2,2−ビス−(3,5−ジブロモ−4−ヒドロキシフェニル)−プロパン、2,2−ビス−(4−ヒドロキシ−3−tert−ブチルフェニル)−プロパン、2,2−ビス−(4−ヒドロキシフェニル)−ブタン(ビスフェノールB)、3,3−ビス−(4−ヒドロキシフェニル)−ペンタン、3,4−ビス−(4−ヒドロキシフェニル)−ヘキサン、4,4−ビス−(4−ヒドロキシフェニル)−ヘプタン、2,4−ビス−(4−ヒドロキシフェニル)−2−メチルブタン、2,4−ビス−(3,5−ジメチル−4−ヒドロキシフェニル)−2−メチルブタン、1,1−ビス−(4−ヒドロキシフェニル)−シクロヘキサン(ビスフェノールZ)、1,1−ビス−(4−ヒドロキシフェニル)−3,3,5−トリメチルシクロヘキサン(ビスフェノールTMC)、1,1−ビス−(4−ヒドロキシフェニル)−フェニルエタン、1,4−ビス−[2−(4−ヒドロキシフェニル)−2−プロピル]−ベンゼン(ビスフェノールP)、1,3−ビス−[2−(4−ヒドロキシフェニル)−2−プロピル]−ベンゼン(ビスフェノールM)、4,4’−ジヒドロキシジフェニル(DOD)、4,4’−ジヒドロキシベンゾフェノン、ビス−(2−ヒドロキシナフタ−1−イル)−メタン、ビス−(4−ヒドロキシナフタ−1−イル)−メタン、1,5−ジヒドロキシナフタレン、トリス−(4−ヒドロキシフェニル)−メタン、1,1,2,2−テトラキス−(4−ヒドロキシフェニル)−エタン、ビス−(4−ヒドロキシフェニル)−エーテル又はビス−(4−ヒドロキシフェニル)−スルホン;
酸性条件下において得られる、フェノールとホルムアルデヒドとの縮合生成物、例えばビスフェノールFノボラックとしても知られるフェノールノボラック又はクレゾールノボラック;
芳香族アミン、例えばアニリン、トルイジン、4−アミノフェノール、4,4’−メチレンジフェニルジアミン、4,4’−メチレンジフェニルジ−(N−メチル)−アミン、4,4’−[1,4−フェニレン−ビス−(1−メチルエチリデン)]−ビスアニリン(ビスアニリンP)、4,4’−[1,3−フェニレン−ビス−(1−メチルエチリデン)]−ビスアニリン(ビスアニリンM)。
飽和又は不飽和、分岐又は未分岐、環状又は開鎖の二官能性、三官能性又は四官能性のC2〜C30アルコール、特にエチレングリコール、プロピレングリコール、ブチレングリコール、ヘキサンジオール、オクタンジオール、ポリプロピレングリコール、ジメチロールシクロヘキサン、ネオペンチルグリコール、ジブロモ−ネオペンチルグリコール、ヒマシ油、トリメチロールプロパン、トリメチロールエタン、ペンタエリスリトール、ソルビトール又はグリセロール、及びアルコキシ化グリセロール又はアルコキシ化トリメチロールプロパンのグリシジルエーテル;
水素化ビスフェノールA、F若しくはA/F液状樹脂、又は水素化ビスフェノールA、F若しくはA/Fのグリシジル化生成物;
アミド又は複素環窒素塩基のN−グリシジル誘導体、例えばトリグリシジルシアヌレート及びトリグリシジルイソシアヌレート、並びにエピクロロヒドリンとヒダントインとの反応生成物;
オレフィン、例えば特にビニルシクロヘキセン、ジシクロペンタジエン、シクロヘキサジエン、シクロドデカジエン、シクロドデカトリエン、イソプレン、1,5−ヘキサジエン、ブタジエン、ポリブタジエン、又はジビニルベンゼンの酸化により得られるエポキシ樹脂;
が含まれる。
溶剤、希釈剤、成膜剤又は増量剤、例えば特に上記で既述の非反応性の希釈剤;
反応性希釈剤、特にエポキシ基を有する反応性希釈剤、例えば上述のもの、エポキシ化ダイズ油又は菜種油、アセトアセテート基を有する化合物、特にアセトアセチル化ポリオール、ブチロラクトン、カーボネート、アルデヒド、並びに更には反応性基を有するイソシアネート及びシリコーン;
ポリマー、特にポリアミド、ポリスルフィド、ポリビニルホルマール(PVF)、ポリビニルブチラール(PVB)、ポリウレタン(PUR)、カルボキシル基を有するポリマー、ポリアミド、ブタジエン−アクリロニトリルコポリマー、スチレン−アクリロニトリルコポリマー、ブタジエン−スチレンコポリマー、不飽和モノマーのホモポリマー又はコポリマー、特にエチレン、プロピレン、ブチレン、イソブチレン、イソプレン、酢酸ビニル及びアルキル−(メタ)アクリレートを含む群から選択される不飽和モノマーのホモポリマー又はコポリマー、特にクロロスルホン化ポリエチレン及びフッ素含有ポリマー、スルホンアミド修飾メラミン、並びに精製モンタンワックス;
無機及び有機フィラー、例えば脂肪酸、特にステアリン酸塩で任意に被覆された重質又は軽質炭酸カルシウム、バライト(重晶石)、タルク、粉末石英、ケイ砂、黒雲母、ドロマイト、ウォラストナイト、カオリン、マイカ(ケイ酸アルミニウムカリウム)、分子篩、酸化アルミニウム、水酸化アルミニウム、水酸化マグネシウム、シリカ、セメント、石膏、フライアッシュ、カーボンブラック、グラファイト、アルミニウム、銅、鉄、亜鉛、銀又は鋼鉄等の金属粉、PVC粉末、又は中空球;
繊維、特にガラス繊維、炭素繊維、金属繊維、セラミック繊維、又はポリアミド繊維若しくはポリエチレン繊維等のプラスチック繊維;
顔料、特に二酸化チタン及び酸化鉄;
上述の促進剤;
レオロジー改質剤、特に増粘剤又は沈降防止剤;
接着促進剤、特にオルガノアルコキシシラン;
酸化、熱、光及びUV照射に対する安定剤;
難燃物質、特に水酸化アルミニウム(ATH)、二水酸化マグネシウム(MDH)、三酸化アンチモン、五酸化アンチモン、ホウ酸(B(OH)3)、ホウ酸亜鉛、リン酸亜鉛、ホウ酸メラミン、シアヌル酸メラミン、ポリリン酸アンモニウム、リン酸メラミン、ピロリン酸メラミン、ポリ臭化ジフェニルオキシド又はジフェニルエーテル、リン酸塩、例えば特にジフェニルクレシルホスフェート、レゾルシノール−ビス−(ジフェニルホスフェート)、レゾルシノール−ジホスフェート−オリゴマー、テトラフェニルレゾルシノールジホスファイト、エチレンジアミンジホスフェート及びビスフェノールA−ビス−(ジフェニルホスフェート)、トリス−(クロロエチル)−ホスフェート、トリス−(クロロプロピル)−ホスフェート及びトリス−(ジクロロイソプロピル)−ホスフェート、トリス−[3−ブロモ−2,2−ビス−(ブロモメチル)−プロピル]−ホスフェート、テトラブロモ−ビスフェノールA、ビスフェノールAのビス−(2,3−ジブロモプロピルエーテル)、臭化エポキシ樹脂、エチレン−ビス−(テトラブロモフタルイミド)、エチレン−ビス−(ジブロモノルボルナンジカルボキシミド)、1,2−ビス−(トリブロモフェノキシ)−エタン、トリス−(2,3−ジブロモプロピル)−イソシアヌレート、トリブロモフェノール、ヘキサブロモシクロドデカン、ビス−(ヘキサクロロシクロペンタジエノ)−シクロオクタン及びクロロパラフィン;
界面活性物質、特に湿潤剤、レベリング剤、脱気剤、及び/又は消泡剤;
殺生物剤、例えば、殺藻剤、殺真菌剤又は真菌成長阻害物質。
(i)少なくとも1種のエポキシ樹脂を含有する樹脂部と、
(ii)上記の硬化剤を含有する硬化剤部と、
からなる二部式組成物である。
ガラス、ガラスセラミック、コンクリート、モルタル、レンガ、タイル、石膏及び天然石、例えば、花崗岩又は大理石;
金属及び合金、例えば、亜鉛めっき及びクロムめっき金属等の表面被覆金属及び合金を含むアルミニウム、鉄、鋼及び非鉄金属;
皮革、織物、紙、木、樹脂、例えばフェノール、メラミン又はエポキシ樹脂によって接着した木材、樹脂繊維複合材及び他のいわゆるポリマー複合材;
プラズマ、コロナ又はフレームにより任意に表面処理されたプラスチック、特に硬質及び軟質PVC、ABS、ポリカーボネート(PC)、ポリアミド(PA)、ポリエステル、PMMA、エポキシ樹脂、PUR、POM、PO、PE、PP、EPM及びEPDM;
繊維強化プラスチック、例えば、炭素繊維強化プラスチック(CFRP)、ガラス繊維強化プラスチック(GRP)及びシート成形コンパウンド(SMC);
被覆基層、例えば、粉体被覆金属又は合金;
塗装及びワニス。
「AHEW」はアミンの水素当量を表す。
「EEW」はエポキシド当量を表す。
粘度は、サーモスタットを備えるRheotec RC30コーンプレート型粘度計(円錐直径50mm、円錐角1度、円錐チップ−プレート間距離0.05mm、剪断速度10s−1)で測定した。
アラルジット(Araldite)(登録商標)DY−K(Huntsman製)、クレシルグリシジルエーテル、EEW およそ182g/Eq
アラルジット(Araldite)(登録商標)GY250(Huntsman製)、ビスフェノールAジグリシジルエーテル、EEW およそ187.5g/Eq
アラルジット(Araldite)(登録商標)DY−E(Huntsman製)、C12〜C14アルコールのモノグリシジルエーテル、EEW およそ290g/Eq
Ancamine(商標)K54(Air Products製)、2,4,6−トリス(ジメチルアミノメチル)フェノール
Vestamin(商標)TMD(Evonik製)、2,2,4−及び2,4,4−トリメチルヘキサメチレン−ジアミン、AHEW 39.6g/Eq
ダイテック(Dytek)(登録商標)A(Invista製)、1,5−ジアミノ−2−メチルペンタン、AHEW 29.0g/Eq
Vestamin(商標)IPD(Evonik製)、3−アミノメチル−3,5,5−トリメチル−シクロヘキシルジアミン(イソホロンジアミン)、AHEW 42.6g/Eq
1,3−BAC(三菱ガス化学株式会社製)、1,3−ビス(アミノメチル)シクロヘキサン、AHEW 35.5g/Eq
MXDA(三菱ガス化学株式会社製)、1,3−ビス(アミノメチル)ベンゼン
ガスカミン(Gaskamine)(登録商標)240(三菱ガス化学株式会社製)、スチレン化1,3−ビス(アミノメチル)ベンゼン、AHEW およそ103g/Eq
ジェファミン(Jeffamine)(登録商標)D−230(Huntsman製)、およそ240g/molの平均分子量のポリオキシプロピレンジアミン、AHEW 60g/Eq
ジェファミン(Jeffamine)(登録商標)RFD−270(Huntsman製)、1,4−ジメチロール−シクロヘキサンのプロポキシ化及びその後のアミノ化による脂環式エーテル基含有ジアミン、平均分子量およそ270g/mol、AHEW 67g/Eq
付加体A−1:
165.7g(1.05mol)のVestamin(商標)TMDをベッセルに入れ、加熱した。窒素雰囲気下でよく撹拌しながら、80℃の温度で2時間かけて、反応混合物の温度が85℃よりも上がらないことを確認しつつ、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kを徐々に添加した。反応混合物を80℃で2時間静置させた後、23℃に冷却し、密閉して、保管した。9.7Pa・sの粘度、341.5mg KOH/gのアミン価、及びおよそ109.1g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
付加体A−1について記載したように、186.1g(1.18mol)のVestamin(商標)TMDを、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。4.8Pa・sの粘度、361.8mg KOH/gのアミン価、及びおよそ99.4g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
付加体A−1について記載したように、186.1g(1.10mol)のVestamin(商標)TMDを、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。6.9Pa・sの粘度、351.3mg KOH/gのアミン価、及びおよそ104.2g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
付加体A−1について記載したように、116.0g(1.00mol)のダイテック(Dytek)(登録商標)Aを、200.2g(1.10mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。13.1Pa・sの粘度、355mg KOH/gのアミン価、及びおよそ109.1g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
付加体A−1について記載したように、116.0g(1.00mol)のダイテック(Dytek)(登録商標)Aを、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。5.8Pa・sの粘度、377mg KOH/gのアミン価、及びおよそ99.4g/Eqの理論AHEWを有する、透明な僅かに黄色がかった高粘度の液体が得られた。
付加体A−1について記載したように、127.6g(1.10mol)のダイテック(Dytek)(登録商標)Aを、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。3.1Pa・sの粘度、401mg KOH/gのアミン価、及びおよそ91.1g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
付加体A−1について記載したように、187.4g(1.10mol)のVestamin(商標)IPDを、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。40℃で測定した17.5Pa・sの粘度、340mg KOH/gのアミン価、及びおよそ108.7g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
付加体A−1について記載したように、156.4g(1.10mol)の1,3−BACを、182.0g(1.00mol)のアラルジット(Araldite)(登録商標)DY−Kと反応させた。59.4Pa・sの粘度、369mg KOH/gのアミン価、及びおよそ99.5g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
ベンジル化MXDA:
丸底フラスコに、17.0g(0.16mol)のベンズアルデヒド及び13.6g(0.10mol)のMXDAを、窒素雰囲気下で十分な量のイソプロパノールに溶解させた。この溶液を30分間23℃で撹拌した後、80barの水素圧、80℃の温度及び3ml/分の流量で、Pd/C固定床触媒を備える連続運転水素付加装置により水素付加した。反応の進行を追うために、IR分光法を使用して、およそ1665cm−1におけるイミンのバンドが消失したかどうかを確認した。その後、溶液を真空中、80℃で濃縮させた。得られた生成物は、20℃における0.1Pa・sの粘度、416.8mg KOH/gのアミン価、及びおよそ115.5g/Eqの理論AHEWを有する、透明な黄色がかった油であった。
ベンジル化MXDAに関するものと同じ方法で、25.6g(0.20mol)の2−エチルヘキサナール及び13.6g(0.10mol)のMXDAを反応させた。20℃における140mPa・sの粘度、308.6mg KOH/gのアミン価、及びおよそ180.3g/Eqの理論AHEWを有する、透明な僅かに黄色がかった液体が得られた。
各実施例について、硬化剤部の指示される量(重量部)で表1〜表4に示される構成要素を、遠心ミキサ(SpeedMixer(商標)DAC150、FlackTek Inc.)を用いて混合し、湿気を排除して保管した。
混合の10分後に、20℃において粘度を求めた(「粘度(10’)」)。
Claims (15)
- エポキシ樹脂を硬化するのに好適な硬化剤であって、トリメチルヘキサメチレンジアミンと、クレシルグリシジルエーテルとの少なくとも1種の付加体を含有する、硬化剤。
- 前記トリメチルヘキサメチレンジアミンが、2,2,4−トリメチル−1,6−ヘキサンジアミン若しくは2,4,4−トリメチル−1,6−ヘキサンジアミン、又はこれらの異性体の混合物であることを特徴とする、請求項1に記載の硬化剤。
- 前記クレシルグリシジルエーテルが、オルト−クレシルグリシジルエーテルであることを特徴とする、請求項1又は2に記載の硬化剤。
- 前記付加体が、0.9〜2.0の範囲のトリメチルヘキサメチレンジアミン分子/クレシルグリシジルエーテル分子において、トリメチルヘキサメチレンジアミンと、クレシルグリシジルエーテルとを反応させることにより得られうることを特徴とする、請求項1〜3のいずれか一項に記載の硬化剤。
- 前記付加体に加えて、エポキシ基に対して反応性の少なくとも2つのアミンの水素を有する少なくとも1種の更なるポリアミンを更に含有することを特徴とする、請求項1〜4のいずれか一項に記載の硬化剤。
- 前記更なるポリアミンが、少なくとも2つの第一級脂肪族アミノ基を有するポリアミンであることを特徴とする、請求項5に記載の硬化剤。
- 前記少なくとも2つの第一級脂肪族アミノ基を有するポリアミンが、イソホロンジアミン、1,3−ビス(アミノメチル)シクロヘキサン、1,4−ビス(アミノメチル)シクロヘキサン、ビス(4−アミノシクロヘキシル)メタン、ビス(4−アミノ−3−メチルシクロヘキシル)メタン、2,5(2,6)−ビス(アミノメチル)ビシクロ[2.2.1]ヘプタン、3(4),8(9)−ビス(アミノメチル)トリシクロ[5.2.1.02,6]デカン、1,3−ビス(アミノメチル)ベンゼン、及び500g/molまでの平均分子量のエーテル基含有ポリアミンからなる群より選択されることを特徴とする、請求項6に記載の硬化剤。
- 前記更なるポリアミンが、少なくとも1つの第二級アミノ基を有するポリアミンであることを特徴とする、請求項5に記載の硬化剤。
- 前記少なくとも1つの第二級アミノ基を有するポリアミンが、N−モノアルキル化及びN,N’−ジアルキル化1,6−ヘキサンジアミン、1,5−ジアミノ−2−メチルペンタン、1,3−ビス(アミノメチル)シクロヘキサン、1,4−ビス(アミノメチル)シクロヘキサン、1,3−ビス(アミノメチル)ベンゼン、ビス(ヘキサメチレン)トリアミン、ジエチレントリアミン、トリエチレンテトラアミン、テトラエチレンペンタアミン、ジプロピレントリアミン、N−(2−アミノエチル)−1,3−プロパンジアミン、及びN,N’−ビス(3−アミノプロピル)エチレンジアミンからなる群から選択され、アルキル基がベンジル、2−フェニルエチル、イソブチル、ヘキシル又は2−エチルヘキシルであることを特徴とする、請求項8に記載の硬化剤。
- 前記硬化剤中における、エポキシ基に対して反応性の前記アミンの水素の5%〜90%が、前記付加体に由来することを特徴とする、請求項5〜9のいずれか一項に記載の硬化剤。
- 非反応性の希釈剤の含量が25wt%未満であることを特徴とする、請求項1〜10のいずれか一項に記載の硬化剤。
- 少なくとも1種のエポキシ樹脂と、請求項1〜11のいずれか一項に記載の硬化剤とを含有する、エポキシ樹脂組成物。
- (i)少なくとも1種のエポキシ樹脂を含有する樹脂部、及び
(ii)請求項1〜11のいずれか一項に記載の硬化剤を含有する硬化剤部
からなる二部式組成物であることを特徴とする、請求項12に記載のエポキシ樹脂組成物。 - 請求項12又は13に記載の組成物を硬化することにより得られる、硬化組成物。
- 請求項14に記載の硬化組成物を含有する物品。
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JP2018020553A (ja) * | 2016-06-23 | 2018-02-08 | エボニック デグサ ゲーエムベーハーEvonik Degussa GmbH | オートクレーブ養生気泡コンクリート(aac)製の強化された建築ブロック |
JP7014532B2 (ja) | 2016-06-23 | 2022-02-01 | エボニック オペレーションズ ゲーエムベーハー | オートクレーブ養生気泡コンクリート(aac)製の強化された建築ブロック |
JP2019218237A (ja) * | 2018-06-20 | 2019-12-26 | 株式会社大林組 | 水中硬化が可能な複合体組成物の製造方法、水中硬化が可能な建設資材の製造方法 |
Also Published As
Publication number | Publication date |
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EP2943518A2 (de) | 2015-11-18 |
WO2014108304A2 (de) | 2014-07-17 |
CN104870509B (zh) | 2018-06-08 |
CN104870509A (zh) | 2015-08-26 |
EP2943518B1 (de) | 2016-11-02 |
AU2013372262A1 (en) | 2015-07-02 |
US9790319B2 (en) | 2017-10-17 |
WO2014108304A3 (de) | 2014-12-18 |
JP6502264B2 (ja) | 2019-04-17 |
US20150344615A1 (en) | 2015-12-03 |
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