JP6236044B2 - 新規な樹脂硬化剤 - Google Patents
新規な樹脂硬化剤 Download PDFInfo
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- JP6236044B2 JP6236044B2 JP2015154373A JP2015154373A JP6236044B2 JP 6236044 B2 JP6236044 B2 JP 6236044B2 JP 2015154373 A JP2015154373 A JP 2015154373A JP 2015154373 A JP2015154373 A JP 2015154373A JP 6236044 B2 JP6236044 B2 JP 6236044B2
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- 238000000034 method Methods 0.000 claims description 5
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- 239000011737 fluorine Substances 0.000 description 11
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
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- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 3
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- 150000002009 diols Chemical class 0.000 description 2
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- PFURGBBHAOXLIO-PHDIDXHHSA-N trans-cyclohexane-1,2-diol Chemical compound O[C@@H]1CCCC[C@H]1O PFURGBBHAOXLIO-PHDIDXHHSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 2
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 description 1
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
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- MRBFWTDIRYEDBQ-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid Chemical compound NCCC1=CC=C(C(O)=O)C=C1 MRBFWTDIRYEDBQ-UHFFFAOYSA-N 0.000 description 1
- LYWVNPSVLAFTFX-UHFFFAOYSA-N 4-methylbenzenesulfonate;morpholin-4-ium Chemical compound C1COCCN1.CC1=CC=C(S(O)(=O)=O)C=C1 LYWVNPSVLAFTFX-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
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- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000004643 cyanate ester Substances 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 229920000642 polymer Polymers 0.000 description 1
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/60—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in meta- or para- positions
-
- 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
- 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
- C07C233/42—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 a carbon atom of a six-membered aromatic ring
- C07C233/43—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 a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/38—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having the nitrogen atom of the carboxamide group bound to a carbon atom of a ring other than a six-membered aromatic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/28—Ethers with hydroxy compounds containing oxirane rings
- C07D303/30—Ethers of oxirane-containing polyhydroxy compounds in which all hydroxyl radicals are etherified with oxirane-containing hydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/36—Compounds containing oxirane rings with hydrocarbon radicals, substituted by nitrogen atoms
-
- 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
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- 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
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3227—Compounds containing acyclic nitrogen atoms
-
- 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
- C08G59/5033—Amines aromatic
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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Description
X1−B−X2
によって表すことができ、式中、X1及びX2の各々は、上記で論じた通り少なくとも1つの官能性反応基を含み、官能性反応基は、例えば芳香族脂環式基又は複素環式基など、堅くて非官能性の環状単位に付着していてよい。例として、ベンゼン、ナフタレン、アントラセン、シクロヘキサン、ピリジン、フラン、チオフェン、好ましくはベンゼンがある。環状単位は、今度は、アルキル、ハロゲン、エステル、及びエーテルなど、さらなる非反応性官能性を有することができる。B配置(sequence)は、X1及びX2の各々において環状単位に結合している。
粉砕した3−ニトロベンゾイルクロリド100グラムを、500mlクロロベンゼン中ジアミノエタン15.43g及びトリエチルアミン27.2gを含む撹拌している容器に、室温で30分かけて加えた。38℃の発熱が記録された。温度を1時間、50℃に上げた。生成物を冷却し、ろ過し、アセトン及び水で洗浄し、真空中で乾燥させて非常に淡い黄色粉末66g(72.5%)を得た。このジニトロ化合物65gを取り、1リットルフラスコ中、窒素ブリードさせながら工業用メタノール変性アルコール250ml中に分散させ、活性炭上10%パラジウム3gを加え、2時間かけてヒドラジン水和物50mlを滴下添加することによって還元した。ニトロ化合物を溶解すると混合物は40℃に発熱し、褐色化した。次いで、温度を70℃に上げ、90分間これを維持し、次いで冷却した。
ジニトロ前駆物質を最初に調製した。trans−1,2−ジアミノシクロヘキサン28.44gを、トリエチルアミン26.4g及びクロロベンゼン300gと一緒に1000mlフラスコ中に秤量した。機械で撹拌しながら、粉末化した3−ニトロベンゾイルクロリド97gを室温で1時間かけて加え、流動性を維持するために必要に応じてさらなるクロロベンゼンを加えた。混合物は30℃に発熱した。混合物を冷却し、ろ過し、IMS及び水で洗浄した。80℃で乾燥させた後、融点266℃の白色粉末71g、収率69%が得られた。
クロロベンゼン(500ml)中trans−1,2−シクロヘキサンジオール(20g)及びトリエチルアミン(36.5g)から、1時間かけて3−ニトロベンゾイルクロリド(67.09g)をゆっくりと加えることによって、ジニトロ前駆物質を調製した。温度を2時間50℃に上げた。生成物をろ過してトリエチルアミン塩酸塩を除去した。ろ液をロータリーエバポレートにかけ、黄色油が得られ、これが結晶化したらろ過し、IMSで洗浄し、融点102〜104℃の白色粉末41g(58%)が得られた。
先のエステル−アミン1に関して、ジオールのp−アミノエチルベンゾエートとのエステル交換反応によって、この化合物の調製を試みた。生成物は単離されなかった。ジオールが立体障害を非常に受けているか、又は非常に揮発性のため周囲圧力で反応できないことが想定される。したがって、通常の酸塩化物/アルコールエステル化反応を使用するのが必要であった。
上記の硬化剤を、エポキシ樹脂との反応について試験した。以下の混合物を調製し、180℃で2時間硬化させた。試験は、TA Instruments DMA上、25℃から250℃まで5℃/分で加熱し、1Hzの周波数を用いて行った。
*この場合、MY721をジグリシジル−1,2−シクロヘキサンカルボキシレート2.84gとブレンドした。
本発明の諸態様は、以下のとおり要約することができる。
[1].
硬化剤が、安定な環状配置に調節できる安定な鎖状配置を有する調節可能な構造単位を含み、環状配置は、化学的吸引相互作用を示す少なくとも2個の末端構成要素を有する鎖状配置の構成要素を含み、2個の末端構成要素を分離することによって環状配置から鎖状配置に調節して戻すことができる、硬化剤を含む硬化性樹脂。
[2].
化学的吸引相互作用が、共有結合よりも弱い、1項に記載の硬化性樹脂。
[3].
化学的吸引相互作用が水素結合である、1項又は2項に記載の硬化性樹脂。
[4].
調節可能な構造単位が、窒素、酸素、又はフッ素に結合している利用可能な水素、及び利用可能な窒素、酸素、又はフッ素の構成要素を含み、利用可能な水素及び利用可能な窒素、酸素、又はフッ素は、3個から10個までの原子構成要素によって分離されている、3項に記載の硬化性樹脂。
[5].
利用可能な窒素、酸素、又はフッ素が酸素である、4項に記載の硬化性樹脂。
[6].
利用可能な水素が窒素に結合している、4項又は5項に記載の硬化性樹脂。
[7].
調節可能な構造単位が−CO−構造を含む、1から6項までのいずれか一項に記載の硬化性樹脂。
[8].
調節可能な単位が少なくとも1個の−CO−単位及び少なくとも1個の−NH−単位を含み、C及びNが1個から8個までの原子構成要素の鎖によって分離されている、7項に記載の硬化性樹脂。
[9].
調節可能な構造単位が−CO−NH−構造を含む、7項又は8項に記載の硬化性樹脂。
[10].
調節可能な構造単位が−CO−O−構造を含む、7から9項までのいずれか一項に記載の硬化性樹脂。
[11].
化学的吸引相互作用が、1kJmol −1 から200kJmol −1 まで、好ましくは2kJmol −1 から50kJmol −1 まで、より好ましくは5kJmol −1 から30kJmol −1 までの強度を有する、1から10項までのいずれか一項に記載の硬化性樹脂。
[12].
各々が対応する鎖状配置からの1個を超える環状配置を形成することができる、1から11項までのいずれか一項に記載の硬化性樹脂。
[13].
2個の異なる鎖状配置から2個の環状配置を形成することができる、12項に記載の硬化性樹脂。
[14].
硬化性樹脂がエポキシ樹脂であり、硬化剤である場合、アミン官能基を有する、1から13項までのいずれか一項に記載の硬化性樹脂。
[15].
X1−B−X2によって表すことができ、X1及びX2の各々が少なくとも1個の官能性反応基を含み、官能性反応基が強固な非官能性の環状単位に付着しており、B配置がX1及びX2の各々において環状単位に結合しているバックボーンを含む、1から14項までのいずれか一項に記載の硬化性樹脂。
[16].
X1基及びX2基上の官能性反応基がB配置に対してメタ又はパラである、15項に記載の硬化性樹脂。
[17].
X1及びX2の各々がベンゼン環であり、−NH 2 官能性反応基がB配置に対してメタ又はパラである硬化剤である、16項に記載の硬化性樹脂。
[18].
B配置が少なくとも2個の−CO−基を含む、15から17項までのいずれか一項に記載の硬化性樹脂。
[19].
B配置が、1個から8個の原子構成要素によって分離されている2個の−CO−NH−構造を含む、18項に記載の硬化性樹脂。
[20].
B配置が、1個から8個の原子構成要素によって分離されている2個の−CO−O−構造を含む、18項に記載の硬化性樹脂。
[21].
B配置が、脂環式基、特にシクロヘキサンを含む、15から20項までのいずれか一項に記載の硬化性樹脂。
[22].
B配置の残りが脂環式基の2個の隣接する炭素に結合している、21項に記載の硬化性樹脂。
[23].
バックボーンが4個から12個までの原子構成要素の鎖を含む、15から22項までのいずれか一項に記載の硬化性樹脂。
[24].
130℃から260℃までの融点を有する、1から23項までのいずれか一項に記載の硬化性樹脂。
[25].
繊維構造、及び1から24項までのいずれか一項に記載の硬化性樹脂を含むプリプレグ材。
[26].
1から24項までのいずれか一項に記載の硬化性樹脂を硬化するプロセスによって得ることができる硬化樹脂。
[27].
100℃を超えるガラス転移温度を有する、26項に記載の硬化樹脂。
Claims (3)
- 3−アミノフェノールのトリグリシジル誘導体を含む硬化性エポキシ樹脂及びこの硬化性エポキシ樹脂のための硬化剤を含む硬化性樹脂であって、
前記硬化剤は、張力、せん断応力、衝撃応力又は屈曲応力に応答して、鎖状配置と環状配置との間を調節可能なものであり、かつ前記硬化剤は、X1−B−X2の式(式中、X1及びX2の各々は、1つのNH2官能性反応基を有するベンゼン環であり、Bは、シクロヘキサンの隣接する炭素に位置する2つの−CO−O−構造からなり、前記NH2官能性反応基が、前記B配置に対してパラ位に位置しており、かつ、この2つの−CO−O−構造が、アキシアル位における両方の炭素でシクロヘキサン基に結合しており、それによって前記硬化剤が鎖状構造を形成している。)で表される、上記硬化性樹脂。 - 繊維構造、及び、請求項1に記載の硬化性樹脂を含むプリプレグ材。
- 請求項1に記載の硬化性樹脂を硬化するプロセスによって得ることができる硬化樹脂。
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GB201402053D0 (en) | 2014-02-06 | 2014-03-26 | Hexcel Composites Ltd | Amino benzoates or benzamides as curing agents for epoxy resins |
US10119001B2 (en) | 2014-02-06 | 2018-11-06 | Hexcel Corporation | Extended room temperature storage of epoxy resins |
US10377916B2 (en) | 2015-09-01 | 2019-08-13 | United States Of America As Represented By The Administrator Of Nasa | Coatings with molecular flexibility for ice adhesion mitigation |
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CN108329222A (zh) * | 2017-12-29 | 2018-07-27 | 江苏湘园化工有限公司 | 一种制备醚、烷基二醇-双-对氨基苯甲酸酯的方法 |
CN111039795A (zh) * | 2019-12-18 | 2020-04-21 | 厦门本素药业有限公司 | (1r,2r)-(-)-n,n`-二甲基-1,2-环己二胺的制备方法 |
CN111019554B (zh) * | 2019-12-23 | 2021-09-10 | 天津渤海化学股份有限公司 | 固化树脂调节剂、双组分环氧体系胶黏剂及其制备方法 |
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US3932360A (en) * | 1974-03-14 | 1976-01-13 | Polaroid Corporation | Polyurethane elastomers prepared from diamine curing agents |
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US4645803A (en) * | 1984-02-29 | 1987-02-24 | American Cyanamid Company | Curable epoxy resin compositions |
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JPH0796607B2 (ja) * | 1987-09-07 | 1995-10-18 | 富山県 | 高分子圧電材及びその製造方法 |
DE4012946A1 (de) * | 1990-04-24 | 1991-10-31 | Basf Ag | Prepreg fuer hochleistungsverbundwerkstoffe |
US5268442A (en) * | 1990-11-13 | 1993-12-07 | Brigham Young University | Chiral copolymers with oligosiloxane spacers |
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GB2460050A (en) * | 2008-05-14 | 2009-11-18 | Hexcel Composites Ltd | Epoxy composite |
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2010
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EP2521747A2 (en) | 2012-11-14 |
WO2011083329A3 (en) | 2011-11-24 |
WO2011083329A2 (en) | 2011-07-14 |
GB201000182D0 (en) | 2010-02-24 |
US8981033B2 (en) | 2015-03-17 |
GB201004722D0 (en) | 2010-05-05 |
JP2015214711A (ja) | 2015-12-03 |
CN102695740A (zh) | 2012-09-26 |
CN102695740B (zh) | 2015-03-25 |
JP2013516533A (ja) | 2013-05-13 |
US20130217803A1 (en) | 2013-08-22 |
ES2881208T3 (es) | 2021-11-29 |
EP2521747B1 (en) | 2021-06-16 |
GB2476841A (en) | 2011-07-13 |
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