JP2018500423A - 複合材料用のエポキシ系樹脂組成物 - Google Patents
複合材料用のエポキシ系樹脂組成物 Download PDFInfo
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- 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 3
- 239000012943 hotmelt Substances 0.000 description 3
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- 229920013657 polymer matrix composite Polymers 0.000 description 3
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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
- 229920003319 Araldite® Polymers 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- VAGOJLCWTUPBKD-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=1)=CC=CC=1N(CC1OC1)CC1CO1 VAGOJLCWTUPBKD-UHFFFAOYSA-N 0.000 description 1
- AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- 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
- C08G59/226—Mixtures of di-epoxy compounds
-
- 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
- C08G59/24—Di-epoxy compounds carbocyclic
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- 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
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- 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
- C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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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
- C08G59/50—Amines
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- C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
- C08L81/06—Polysulfones; Polyethersulfones
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- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
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- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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- Polymers & Plastics (AREA)
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- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
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Abstract
Description
本発明の一実施態様によれば、エポキシ系樹脂組成物は:
(A)エポキシ成分であって:
(i)以下の構造(I)によって表わされるビスフェノールF二官能性エポキシ:
(ii)以下の構造(II)によって表わされるアントラシル化合物:
;及び
(iii)三官能性エポキシ
を含む、エポキシ成分と、
(B)熱可塑性ポリマーと;
(C)アミン含有硬化剤と
を含有し、
エポキシ成分の100重量部につき、三官能性エポキシが30部未満、好ましくは20〜29部の量で存在し、二官能性エポキシがアントラシル化合物より多い量で存在する。
49〜51部の二官能性エポキシ、
24〜26部のアントラシル化合物、及び
23〜25部の三官能性エポキシ樹脂
を含有する。
4−グリシジルオキシ−N,N−ジグリシジルアニリン(Huntsman Advanced MaterialsからAraldite(登録商標)MY0510として市販);
3−グリシジルオキシ−N,N−ジグリシジルアニリン(Huntsman Advanced MaterialsからAraldite(登録商標)MY0610として市販)
が含まれる。
本明細書に記載されるエポキシ系樹脂組成物は、複合材料、特にプリプレグを作製するために適している。この文脈における複合材料は、繊維強化樹脂複合材を指し、これはマトリックス樹脂に埋め込まれた強化樹脂からなる。本明細書で使用される用語「プリプレグ」は、硬化性マトリックス樹脂を含浸させた一層の繊維材料を指す。繊維強化材料は、織布又は不織布のプライの形態とするか、又は一方向性のテープの形態とすることができる。「一方向性テープ」は、シート状の構成において同じ方向に整列した一層の強化繊維を指す。本明細書で使用される用語「プリプレグレイアップ」は、積層配列にレイアップされた複数のプリプレグプライを指す。例として、プリプレグプライの数は2〜100、又は10〜50とすることができる。
(1)溶融した含浸用のマトリックス樹脂組成物の(温)浴槽に繊維を連続的に通し、繊維を完全に又は実質的に完全に湿らせること;又は
(2)一番上と下の樹脂フィルムを、平行に配置された連続的な一方向性繊維又はファブリックプライに対して押し付けながら、80℃から300℃の範囲内の温度で加熱すること
が含まれる。
エポキシ樹脂組成物を、以下の表1に示す配合組成に従って調製した。成分A〜Eの量は重量部で示される。
2Mitsubishi Chemical Corporationにより供給された
3Huntsman Advanced Materialsにより供給された
比較のために、実施例1において上述したものと同じ方法により、表2に開示の樹脂配合組成を用いてプリプレグ試料を調製した。成分B〜Eの量は重量部で示される。
5Sumika Excelにより供給された
Claims (11)
- (A)エポキシ成分であって:
(i)以下の構造(I)によって表わされるビスフェノールF二官能性エポキシ:
(ii)以下の構造(II)によって表わされるアントラシル化合物:
;及び
(iii)三官能性エポキシ
を含む、エポキシ成分と、
(B)ポリエーテルスルホン(PES)、ポリエーテルエーテルスルホン(PEES)、末端アミン基を有するPES−PEESコポリマーから選択される熱可塑性ポリマーと、
(C)アミン含有硬化剤と
を含み、
エポキシ成分の100重量部につき、三官能性エポキシが30部未満、好ましくは20〜29部の量で存在し、二官能性エポキシがアントラシル化合物より多い量で存在し、
アミン含有硬化剤に対するエポキシ成分の比が、エポキシド基1モルにつき0.7〜0.8モルのアミン−水素基が存在するようなものである、
硬化性エポキシ系樹脂組成物。 - 三官能性エポキシ樹脂が以下の構造(III):
によって表わされる、請求項1に記載の硬化性エポキシ系樹脂組成物。 - アミン含有硬化剤がジアミノジフェニルスルホン(DDS)又はフルオレンアミンである、請求項1に記載の硬化性エポキシ系樹脂組成物。
- 二官能性エポキシに対するアントラシル化合物の重量比が0.4〜0.6である、請求項1に記載の硬化性エポキシ系樹脂組成物。
- エポキシ成分100重量部につき:
49〜51部の二官能性エポキシ、
24〜26部のアントラシル化合物、及び
23〜25部の三官能性エポキシ樹脂
を含む、請求項1に記載の硬化性エポキシ系樹脂組成物。 - 熱可塑性ポリマーが、末端アミン基を有するPES−PEESコポリマーである、請求項1から5のいずれか一項に記載の硬化性エポキシ系樹脂組成物。
- 請求項1から6のいずれか一項に記載の硬化性エポキシ系樹脂組成物に埋め込まれた又は同硬化性エポキシ系樹脂組成物を注入した強化繊維を含む複合材料。
- 強化繊維が:炭素繊維、アラミド繊維、及びファイバーグラス繊維から選択される、請求項7に記載の複合材料。
- 請求項1から6のいずれか一項に記載の硬化性エポキシ系樹脂組成物を含浸させた一方向性繊維を含むプリプレグ。
- 一方向性繊維が:炭素繊維、アラミド繊維、及びファイバーグラス繊維から選択される、請求項9に記載のプリプレグ。
- 積層配列に配置されて、各々が請求項1から6のいずれか一項に記載の硬化性エポキシ系樹脂組成物を含浸させた一方向性繊維を含む複数のプリプレグを含む複合積層体。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201462092448P | 2014-12-16 | 2014-12-16 | |
US62/092,448 | 2014-12-16 | ||
PCT/US2015/065651 WO2016100244A1 (en) | 2014-12-16 | 2015-12-15 | Epoxy-based resin composition for composite materials |
Publications (2)
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WO2019203291A1 (ja) * | 2018-04-20 | 2019-10-24 | 三菱瓦斯化学株式会社 | 熱硬化性組成物、プリプレグ、積層板、金属箔張積層板、プリント配線板及び多層プリント配線板 |
WO2022039104A1 (ja) * | 2020-08-20 | 2022-02-24 | 日鉄ケミカル&マテリアル株式会社 | エポキシ樹脂組成物及び硬化物 |
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WO2020003122A1 (en) * | 2018-06-27 | 2020-01-02 | 3M Innovative Properties Company | Curable compositions and related methods |
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WO2019203291A1 (ja) * | 2018-04-20 | 2019-10-24 | 三菱瓦斯化学株式会社 | 熱硬化性組成物、プリプレグ、積層板、金属箔張積層板、プリント配線板及び多層プリント配線板 |
JPWO2019203291A1 (ja) * | 2018-04-20 | 2021-05-20 | 三菱瓦斯化学株式会社 | 熱硬化性組成物、プリプレグ、積層板、金属箔張積層板、プリント配線板及び多層プリント配線板 |
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CA2968081A1 (en) | 2016-06-23 |
TWI694110B (zh) | 2020-05-21 |
BR112017010254B1 (pt) | 2021-11-03 |
RU2017125004A (ru) | 2019-01-17 |
BR112017010254A2 (pt) | 2018-02-06 |
AU2015362756A1 (en) | 2017-05-18 |
JP6637503B2 (ja) | 2020-01-29 |
RU2017125004A3 (ja) | 2019-02-27 |
EP3233960B1 (en) | 2019-02-20 |
ES2726680T3 (es) | 2019-10-08 |
CA2968081C (en) | 2022-11-22 |
US20160168372A1 (en) | 2016-06-16 |
US9884959B2 (en) | 2018-02-06 |
TW201627396A (zh) | 2016-08-01 |
CN107108854A (zh) | 2017-08-29 |
EP3233960A1 (en) | 2017-10-25 |
WO2016100244A1 (en) | 2016-06-23 |
CN107108854B (zh) | 2019-03-29 |
AU2015362756B2 (en) | 2019-02-14 |
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