JP2021119221A - エポキシ樹脂 - Google Patents
エポキシ樹脂 Download PDFInfo
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- JP2021119221A JP2021119221A JP2021062577A JP2021062577A JP2021119221A JP 2021119221 A JP2021119221 A JP 2021119221A JP 2021062577 A JP2021062577 A JP 2021062577A JP 2021062577 A JP2021062577 A JP 2021062577A JP 2021119221 A JP2021119221 A JP 2021119221A
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- Prior art keywords
- formula
- compound
- epoxy resin
- curable epoxy
- resin preparation
- 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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- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 127
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 124
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 53
- 239000000835 fiber Substances 0.000 claims abstract description 34
- 239000000463 material Substances 0.000 claims abstract description 30
- 239000002131 composite material Substances 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims description 75
- 238000004519 manufacturing process Methods 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 19
- 239000011347 resin Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 239000004593 Epoxy Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 150000004985 diamines Chemical group 0.000 claims description 12
- 125000003700 epoxy group Chemical group 0.000 claims description 12
- 239000011159 matrix material Substances 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 239000002657 fibrous material Substances 0.000 claims description 10
- -1 alicyclic amine Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 3
- 150000004982 aromatic amines Chemical class 0.000 claims description 3
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical group OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
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- 239000000203 mixture Substances 0.000 abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 14
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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 54
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
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- 239000000243 solution Substances 0.000 description 28
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N isopropyl alcohol Natural products CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229910004298 SiO 2 Inorganic materials 0.000 description 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
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- HURSUNYVRTZMIX-UHFFFAOYSA-N 2-[[4-[4-[4-(oxiran-2-ylmethoxy)phenoxy]phenoxy]phenoxy]methyl]oxirane Chemical compound C(C1CO1)OC1=CC=C(OC2=CC=C(C=C2)OC2=CC=C(C=C2)OCC2CO2)C=C1 HURSUNYVRTZMIX-UHFFFAOYSA-N 0.000 description 7
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000004848 polyfunctional curative Substances 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 5
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- 125000003118 aryl group Chemical group 0.000 description 5
- 238000000132 electrospray ionisation Methods 0.000 description 5
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 description 5
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- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 4
- WUPRYUDHUFLKFL-UHFFFAOYSA-N 4-[3-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(OC=2C=CC(N)=CC=2)=C1 WUPRYUDHUFLKFL-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UVXIFYUJZWURAR-UHFFFAOYSA-N [3-(4-aminobenzoyl)phenyl]-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(C(=O)C=2C=CC(N)=CC=2)=C1 UVXIFYUJZWURAR-UHFFFAOYSA-N 0.000 description 4
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- 239000000377 silicon dioxide Substances 0.000 description 4
- 241000894007 species Species 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- QGMGHALXLXKCBD-UHFFFAOYSA-N 4-amino-n-(2-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1C(=O)NC1=CC=CC=C1N QGMGHALXLXKCBD-UHFFFAOYSA-N 0.000 description 3
- LNZYGCIEXZSTCV-UHFFFAOYSA-N CN(CC1OC1)CC1OC1 Chemical compound CN(CC1OC1)CC1OC1 LNZYGCIEXZSTCV-UHFFFAOYSA-N 0.000 description 3
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- FYDKNKUEBJQCCN-UHFFFAOYSA-N lanthanum(3+);trinitrate Chemical compound [La+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O FYDKNKUEBJQCCN-UHFFFAOYSA-N 0.000 description 3
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- HIXFSHWMTVMNID-UHFFFAOYSA-N 1,3-bis(3-methoxyphenoxy)benzene Chemical compound COC1=CC=CC(OC=2C=C(OC=3C=C(OC)C=CC=3)C=CC=2)=C1 HIXFSHWMTVMNID-UHFFFAOYSA-N 0.000 description 2
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- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
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- C07D303/02—Compounds containing oxirane rings
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/14—Peroxides
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- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
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- C08K5/00—Use of organic ingredients
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Abstract
Description
本願は、2016年7月25日に出願された米国仮出願番号62/366,443号の優先権、及び2016年10月4日に出願された豪州仮出願番号第2016904019号の優先権を主張するものであり、これらの内容は、参照によってここに組み込まれる。
式中、
X1はそれぞれ同じであり、かつO及びC(O)から選択され、
X2はそれぞれ同じであり、かつC(O)から選択され、
R1がそれぞれ水素であり、かつR2がそれぞれエポキシド基から選択されるか、又はR2がそれぞれ水素であり、かつR1がそれぞれエポキシド基から選択される。
(a)X1がOであるとき、エポキシド基は、
であり、
(b)X1がC(O)であるとき、エポキシド基は、
であり、かつ
(c)X2がC(O)であるとき、
(i)R2がHであり、かつR1が、
若しくは、
であるか、又は
(ii)R1がHであり、かつR2が、
である。
エポキシ樹脂が、式3の化合物:
を含み、
式中、
Xはそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
Rはそれぞれ同じであり、かつエポキシド基であり、かつ
硬化剤は、式4:
のジアミン硬化剤を含み、
式中、Yはそれぞれ同じであり、かつO、CH2及びC(O)から選択される。
a)
(i)ここで規定する硬化性エポキシ樹脂調製物、及び
(ii)繊維材料、
を提供する工程、及び
b)工程(a)の樹脂調製物を、(i)工程(a)の繊維材料と組み合わせ、(ii)材料を硬化可能な高温に供し、含浸された繊維強化材料を形成する工程
を含むものである。
i)式5の化合物を、式6の化合物と一緒に、触媒の存在下で反応させて、式7の化合物を形成する工程、式中、Pは保護基であり、Mは金属であり、LGは脱離基である:
ii)式7の化合物を、酸触媒によりさらに反応させて、式8の化合物を形成する工程:
を含むものである。
本開示について様々な例を利用可能なことが評価されるであろうが、以下では下記の図面を参照して、幾つかの例を説明する。
用語
エポキシド含有化合物
式中、
X1はそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
R1がそれぞれ水素であり、かつR2がそれぞれエポキシド基から選択されるか、又はR2がそれぞれ水素であり、かつR1がそれぞれエポキシド基から選択される。
式中、
X2はそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
R1がそれぞれ水素であり、かつR2がそれぞれエポキシド基から選択されるか、又はR2がそれぞれ水素であり、かつR1がそれぞれエポキシド基から選択される。
式中、
X2はそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
R2はそれぞれ、エポキシド基から選択される。
置換基X1、X2、R1及びR2
エポキシド基
ここでエポキシ樹脂が、式3の化合物:
を含み、
式中、
Xはそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
Rはそれぞれ同じであり、かつエポキシド基である。
ここでエポキシ樹脂が、式3の化合物:
を含み、
式中、
Xはそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
Rはそれぞれ同じであり、かつエポキシド基である。
ここでエポキシ樹脂が、式3の化合物:
を含み、
式中、
Xはそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
Rはそれぞれ同じであり、かつエポキシド基であり、かつ
硬化剤は、式4のジアミン硬化剤:
を含み、
式中、Yはそれぞれ同じであり、かつO、CH2及びC(O)から選択される。
ここでエポキシ樹脂が、式3の化合物:
を含み、
式中、
Xはそれぞれ同じであり、かつO、CH2及びC(O)から選択され、
Rはそれぞれ同じであり、かつエポキシド基であり、かつ
硬化剤は、式4のジアミン硬化剤:
を含み、
式中、Yはそれぞれ同じであり、かつO、CH2及びC(O)から選択される。
置換基R及びX
a)塗膜形成剤、例えばジカルボン酸のエステル(例えばLusolvan FBH、BASF)、及びグリコールエーテル(例えばDowanol、Dow)、並びに
b)表面活性剤、例えば脂肪酸誘導体(例えばBermadol SPS 2543、Akzo)、及び第四級アンモニウム塩
を含むことができる。
複合材
a)
(i)ここで規定する硬化性エポキシ樹脂調製物、及び
(ii)繊維材料、
を提供する工程、及び
b)工程(a)の樹脂調製物を、(i)工程(a)の繊維材料と組み合わせ、(ii)材料を硬化可能な高温に供し、含浸された繊維強化材料を形成する工程
を含むものである。
i)式5の化合物を、式6の化合物と一緒に、触媒の存在下で反応させて、式7の化合物を形成する工程、式中、Pは保護基であり、Mは金属であり、LGは脱離基である:
ii)式7の化合物を、酸触媒によりさらに反応させて、式8の化合物を形成する工程:
を含むものである。
略語
・1,4−ビス(4−アミノフェノキシ)ベンゼン(TPE−Q)5.84g(2.00×10−2モル);
・エピクロロヒドリン(27.75g、3.00×10−1モル)
・ジクロロエタン(50ml)
・硝酸ランタン六水和物(55mg)
・NaOH(4.00g、1.00×10−1モル)、及び
・イソプロパノール(30ml)。
実施例2:N,N,N,N−テトラグリシジル 1,3−ビス−(4−アミノフェノキシ)ベンゼン(134−TGAPB)の合成
・1,3−ビス(4−アミノフェノキシ)ベンゼン(TPE−R)5.84g(2.00×10−2モル);
・エピクロロヒドリン(27.75g、3.00×10−1モル)
・ジクロロエタン(50ml)
・硝酸ランタン六水和物(55mg)
・NaOH(4.0g、1.00×10−1モル)、及び
・イソプロパノール(30ml)。
実施例3:N,N,N,N−テトラグリシジル 1,3−ビス−(3−アミノフェノキシ)ベンゼン(133−TGAPB)の合成
・1,3−ビス(3−アミノフェノキシ)ベンゼン(133−APB)5.84g(2.00×10−2モル);
・エピクロロヒドリン(27.75g、3.00×10−1モル)
・ジクロロエタン(50ml)
・硝酸ランタン六水和物(55mg)
・NaOH(4.0g、1.00×10−1モル)、及び
・イソプロパノール(30ml)。
実施例4:1,3−ビス−(3−グリシジルオキシフェノキシ)ベンゼン(133−BGOPB)の合成
工程1:1,3−ビス−(3−メトキシフェノキシ)ベンゼンの合成
工程2:1,3−ビス−(3−ヒドロキシフェノキシ)ベンゼン(133−BGOPB)の合成
工程3:1,3−ビス−(3−グリシジルオキシフェノキシ)ベンゼン(133−BGOPB)の合成
実施例5:1,4−ビス−(4−グリシジルオキシフェノキシ)ベンゼン(144−BGOPB)の合成
工程1:1,4−ビス−(4−アセトフェノキシ)ベンゼンの合成
工程2:1,4−ビス−(4−アセトキシフェノキシ)ベンゼンの合成
工程3:1,4−ビス−(4−ヒドロキシフェノキシ)ベンゼンの合成
工程4:1,4−ビス−(4−グリシジルオキシフェノキシ)ベンゼン(144−BGOPB)の合成
実施例6:メタ置換されたヒドロキシ前駆体を、エポキシ樹脂にする合成
工程1:ZnCl2/SiO2触媒の製造
工程2:ビス(4−ヒドロキシフェニル)m−キシレン(BHPmX)の実験室スケールでの合成
実施例7:パラ置換されたヒドロキシ前駆体を、エポキシ樹脂にする合成
工程1:ZnCl2/SiO2触媒の製造
工程2:ビス(4−ヒドロキシフェニル)−p−キシレン(BHPpX)の大規模合成
実施例8:ビス−ヒドロキシフェニル−m−キシレン(BHPmX)及びビス−ヒドロキシフェニル−p−キシレン(BHPpX)の異性体組成物
ヒドロキシ及びエポキシ樹脂合成についての概要
BHPmX
1.反応後に触媒を濾別し、DCMを完全に蒸発させる。
2.油っぽい生成物を、水で連続的に洗浄してフェノールを除去する。フェノール除去における洗浄工程を補助するので、このことは利点である。
3.最終的な生成物は、3種の異性体、高分子量のオリゴマーを含む油であり、収率は実験室で約75%である。
BHPpX
1.反応後、触媒を濾別し、生成物が溶液から晶出するまで、DCM体積を減少させる。
2.生成物をろ過して、3種の異性体を有する白色の固体を生成する。しかしながら、第三の異性体、すなわち2,2置換された異性体は、極めて低い濃度でしか存在しない。
3.最終的な生成物は、収率が約50%であり、高分子量のオリゴマーは、極めて僅かしか認められない。
実施例9:ビス(ヒドロキシフェニル)−p−キシレン(BHPpX)合成のスケールアップ
実施例10:カルボニル結合された芳香族アミン、1,3−ビス(3−アミノベンゾイル)ベンゼン(133BABB)、1,3−ビス(4−アミノベンゾイル)ベンゼン(134BABB)、及び1,4−ビス(4−アミノベンゾイル)ベンゼン(144BABB)の硬化、及び同定
樹脂の製造
・ビスフェノールA(BisA)のグリシジルエーテル
・ビスフェノールF(BisF)のグリシジルエーテル、及び
・1,4ビス(4−グリシジルエーテルフェノキシ)ベンゼン(144BGOPB)、
・1,3−ビス(3−アミノベンゾイル)ベンゼン(133BABB)
・1,3−ビス(4−アミノベンゾイル)ベンゼン(134BABB)、及び
・1,4−ビス(4−アミノベンゾイル)ベンゼン(144BABB)。
例11:メチレン結合された芳香族エポキシ樹脂、ビスアミン、1,3−ビス(3−アミノベンゾイル)ベンゼン(133BABB)、1,3−ビス(4−アミノベンゾイル)ベンゼン(134BABB)及び1,4−ビス(4−アミノベンゾイル)ベンゼン(144BABB)の硬化及び同定
樹脂の製造
表5:例11の44DDS及びMDAの硬化された系についてのtanデルタスペクトルから測定された、硬化後のTg値
例12:44ジアミノジフェニルスルホン(44DDS)で硬化された、1,4−ビス(4−グリシジルオキシフェノキシ)ベンゼン(144BGOPB)及び1,3−ビス(3−グリシジルオキシフェノキシ)ベンゼン(133BGOPB)の硬化及び同定と、44ジアミノジフェニルスルホン(44DDS)で硬化された、ビスフェノールA(BisA)のジグリシジルエーテル、及びビスフェノールF(BisF)のジグリシジルエーテルの硬化及び同定の比較
試料製造
同定
Claims (33)
- X1がそれぞれ、C(O)である、請求項1から3のいずれか一項に記載の化合物。
- 請求項1から6のいずれか一項に記載の化合物と、硬化剤とを含む、硬化性エポキシ樹脂調製物。
- 硬化剤が、脂肪族アミン、脂環式アミン、又は芳香族アミンである、請求項7に記載の硬化性エポキシ樹脂調製物。
- 硬化剤がジアミン硬化剤である、請求項7又は8に記載の硬化性エポキシ樹脂調製物。
- Y及びXがそれぞれ同じである、請求項10から14のいずれか一項に記載の硬化性エポキシ樹脂調製物。
- Y及びXがそれぞれ同じであり、かつO又はC(O)から選択される、請求項10から15のいずれか一項に記載の硬化性エポキシ樹脂調製物。
- X1がそれぞれ同じであり、かつO及びC(O)から選択される、請求項17から21のいずれか一項に記載の硬化性エポキシ樹脂調製物。
- X2がそれぞれ同じであり、かつO及びC(O)から選択される、請求項17から21のいずれか一項に記載の硬化性エポキシ樹脂調製物。
- X1がそれぞれ、C(O)である、請求項22に記載の硬化性エポキシ樹脂調製物。
- X2がそれぞれ、C(O)である、請求項23に記載の硬化性エポキシ樹脂調製物。
- さらに1つ又は複数の添加剤を含む、請求項7から25のいずれか一項に記載の硬化性エポキシ樹脂調製物。
- 請求項7から25のいずれか一項に記載の硬化性エポキシ樹脂調製物で含侵された繊維を含む、含浸された繊維強化材料。
- 硬化されたエポキシ樹脂が、請求項7から25のいずれか一項に記載の硬化性エポキシ樹脂調製物から形成されている、硬化されたエポキシ樹脂のマトリックス内に繊維材料を含む複合材。
- 以下の工程:
a)
(i)請求項7から25のいずれか一項に記載の硬化性エポキシ樹脂調製物、及び
(ii)繊維材料、
を提供する工程、及び
b)工程(a)の樹脂調製物を、(i)工程(a)の繊維材料と組み合わせ、(ii)材料を硬化可能な高温に供し、含浸された繊維強化材料を形成する工程
を含む、含浸された繊維強化材料を形成する方法。 - 硬化性エポキシ樹脂としての、又は硬化性エポキシ樹脂調製物の製造における、請求項1から6のいずれか一項に記載の化合物の使用。
- 含浸された繊維強化材料又はその複合材の製造において、硬化性エポキシ樹脂調製物を使用する、請求項30に記載の使用。
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CN115057991A (zh) | 2022-09-16 |
JP2019527753A (ja) | 2019-10-03 |
EP3487904A4 (en) | 2020-06-10 |
JP7475975B2 (ja) | 2024-04-30 |
EP4148047A1 (en) | 2023-03-15 |
US20230312812A1 (en) | 2023-10-05 |
JP2024056737A (ja) | 2024-04-23 |
US11059937B2 (en) | 2021-07-13 |
US20210355269A1 (en) | 2021-11-18 |
EP3487904A1 (en) | 2019-05-29 |
US20190248953A1 (en) | 2019-08-15 |
CN109642018A (zh) | 2019-04-16 |
JP2020183529A (ja) | 2020-11-12 |
JP6943945B2 (ja) | 2021-10-06 |
US11718707B2 (en) | 2023-08-08 |
CA3231558A1 (en) | 2018-02-01 |
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