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WO2023032943A1 - Composition thermodurcissable - Google Patents

Composition thermodurcissable Download PDF

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Publication number
WO2023032943A1
WO2023032943A1 PCT/JP2022/032494 JP2022032494W WO2023032943A1 WO 2023032943 A1 WO2023032943 A1 WO 2023032943A1 JP 2022032494 W JP2022032494 W JP 2022032494W WO 2023032943 A1 WO2023032943 A1 WO 2023032943A1
Authority
WO
WIPO (PCT)
Prior art keywords
thermosetting composition
composition according
thermosetting
thermoset
acetone
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.)
Ceased
Application number
PCT/JP2022/032494
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English (en)
Japanese (ja)
Inventor
謙一 八木
恭子 中井
雄一 加藤
栄一 須藤
聖史 酒井
修 馬渕
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toyoda Gosei Co Ltd
Original Assignee
Toyoda Gosei Co Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Toyoda Gosei Co Ltd filed Critical Toyoda Gosei Co Ltd
Priority to DE112022003178.6T priority Critical patent/DE112022003178T5/de
Publication of WO2023032943A1 publication Critical patent/WO2023032943A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

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
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4014—Nitrogen containing compounds
    • C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
    • 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
    • C08G59/68—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 catalysts used
    • C08G59/686—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 catalysts used containing nitrogen

Definitions

  • thermosetting compositions relate to thermosetting compositions.
  • thermosetting compositions are widely used in various applications such as fiber-reinforced plastics and adhesive materials. Such thermosetting compositions are disclosed, for example, in US Pat.
  • thermosetting compositions have been conventionally studied, including Patent Document 1 and Patent Document 2.
  • Patent Document 1 Technologies related to thermosetting compositions have been conventionally studied, including Patent Document 1 and Patent Document 2.
  • the current situation is that the technique for improving the mechanical properties of the resulting thermoset is insufficient.
  • thermosetting composition capable of forming a thermoset having excellent mechanical properties. It is to provide things.
  • thermosetting composition containing a main agent having a glycidyl ether group and a solid latent curing agent, and having a particle size of 40 ⁇ m or less before thermosetting.
  • thermosetting composition according to ⁇ 1> which has a viscosity at 25°C of 24 Pa ⁇ s or less as measured with an E-type viscometer.
  • thermoset obtained by heat-curing the thermosetting composition at 150 ° C. for 30 minutes is added with 15.8 times the mass of acetone of the thermoset, and ultrasonically treated for 30 minutes with an ultrasonic disperser.
  • thermosetting composition according to ⁇ 1> or ⁇ 2> wherein the dry matter of the acetone extraction solution obtained by applying is 1.1% by mass or less with respect to the total amount of the thermosetting composition.
  • ⁇ 4> The thermosetting composition according to any one of ⁇ 1> to ⁇ 3>, wherein the latent curing agent is 1 equivalent with respect to the epoxy equivalent of the main agent.
  • ⁇ 5> The thermosetting composition according to any one of ⁇ 1> to ⁇ 4>, wherein the latent curing agent contains dicyandiamide.
  • thermosetting composition according to ⁇ 5>, which is 0.036 or less.
  • thermosetting composition according to ⁇ 6> wherein the intensity ratio I CN /I CO obtained from the acetone extraction solution has a coefficient of variation obtained by dividing the standard deviation by the average value of 0.22 or less. thing.
  • ⁇ 8> The thermosetting composition according to any one of ⁇ 1> to ⁇ 7>, wherein the main agent is bisphenol A diglycidyl ether.
  • ⁇ 9> The thermosetting composition according to any one of ⁇ 1> to ⁇ 8>, which contains a curing accelerator.
  • the curing accelerator contains 3-(3,4-dichlorophenyl)-1,1-dimethylurea.
  • thermosetting composition capable of forming a thermoset with excellent mechanical properties is provided.
  • thermosetting composition according to the present disclosure.
  • a numerical range indicated using the symbol “ ⁇ ” means a range including the numerical values before and after the symbol “ ⁇ ” as the minimum and maximum values, respectively.
  • the upper limit or lower limit described in a certain numerical range may be replaced with the upper limit or lower limit of another numerical range described step by step.
  • upper or lower limits described in a certain numerical range may be replaced with values shown in Examples.
  • the content of each component means the total amount of the multiple types of substances unless otherwise specified when there are multiple types of substances corresponding to each component.
  • thermosetting composition contains a main agent having a glycidyl ether group and a solid latent curing agent, and has a particle size of 40 ⁇ m or less before heat curing.
  • thermosetting compositions containing a main agent and a latent curing agent are widely used, and thermosetting products obtained from such thermosetting compositions are evaluated for degree of curing and mechanical properties. It is for example, as described in Patent Literature 1 and Patent Literature 2, spectroscopy is used to evaluate the degree of curing. However, the techniques described in these patent documents may result in insufficient mechanical properties of thermosets.
  • thermosetting composition according to the present disclosure contains a latent curing agent and has a particle size of 40 ⁇ m or less. That is, the particle size before heat curing is 40 ⁇ m or less, and the latent curing agent is uniformly dispersed. Therefore, when the thermosetting composition is cured, the thermosetting progresses uniformly, so local unevenness in curing can be reduced. Therefore, the degree of thermosetting can be increased as a whole, and a thermoset having excellent mechanical properties can be obtained.
  • the main agent having a glycidyl ether group (hereinafter sometimes simply referred to as "main agent”) is not particularly limited as long as it has a glycidyl ether group.
  • bisphenol A diglycidyl ether bisphenol F diglycidyl ether, triphenylglycidyl ether methane, tris(glycidyloxy)methane, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, tetraphenylglycidyl ether ethane, pentaerythritol poly
  • examples include glycidyl ether, tetraglycidyl ether of 1,6-bis(2-naphthyl)methane, triglycidyl ether of phloroglucinol, and epoxy resins.
  • epoxy resins include phenol novolak type epoxy resin, alkylphenol novolak type epoxy resin, naphthalene-containing novolak type epoxy resin, bisphenol A novolak type epoxy resin, triphenylmethane type (trisphenolmethane type) epoxy resin, and tetrakisphenolethane type epoxy resin.
  • Main agents having glycidyl ether groups are bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, triphenylglycidyl ether methane, tris(glycidyloxy)methane, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, and tetraphenylglycidyl.
  • It preferably contains one or more selected from the group consisting of ether ethane, pentaerythritol polyglycidyl ether, tetraglycidyl ether of 1,6-bis(2-naphthyl)methane, and triglycidyl ether of phloroglucinol.
  • the main agent preferably contains bisphenol A diglycidyl ether.
  • a main agent may be used individually by 1 type, and may be used in combination of 2 or more types.
  • the content of the main agent is not particularly limited, and may be, for example, 40% by mass or more relative to the total amount of the thermosetting composition.
  • the type of latent curing agent is not particularly limited, and examples thereof include dicyandiamide, imidazole compounds, organic acid hydrazides, and amine imide compounds.
  • a latent curing agent is a compound that latently has the function of initiating curing by heat.
  • the latent curing agent preferably contains dicyandiamide.
  • a latent hardening agent may be used individually by 1 type, and may be used in combination of 2 or more types.
  • the content of the latent curing agent may be adjusted as appropriate in consideration of the epoxy equivalent of the main agent and the equivalent of the latent curing agent. It is preferably between 0.36 equivalents and 0.72 equivalents.
  • thermosetting composition has a particle size of 40 ⁇ m or less before heat curing.
  • the latent curing agent is uniformly dispersed, and when the thermosetting composition is cured, the thermosetting progresses uniformly, so that local unevenness in curing can be reduced. Therefore, the degree of thermosetting can be increased as a whole, and a thermoset having excellent mechanical properties can be obtained.
  • thermosetting composition preferably has a viscosity at 25° C. measured with an E-type viscometer (hereinafter sometimes simply referred to as “viscosity”) of 25 Pa ⁇ s or less.
  • viscosity a viscosity at 25° C. measured with an E-type viscometer (hereinafter sometimes simply referred to as “viscosity”) of 25 Pa ⁇ s or less.
  • the viscosity is more preferably 23 Pa ⁇ s or less, even more preferably 22 Pa ⁇ s or less. Moreover, the lower limit of the viscosity is not particularly limited, and the lower the better.
  • thermoset obtained by thermally curing the thermosetting composition at 150 ° C. for 30 minutes is added with 15.8 times the mass of acetone and subjected to ultrasonic treatment for 30 minutes with an ultrasonic disperser. It is preferable that the dry matter of the resulting acetone-extracted solution (hereinafter sometimes simply referred to as “acetone-extracted liquid”) is 1.2% by mass or less with respect to the total amount of the thermoset.
  • acetone extraction rate The mass ratio of the dried product to the total amount of the thermoset product is sometimes called "acetone extraction rate" [%].
  • the acetone extraction rate corresponds to the ratio of the uncured thermosetting composition extracted from the thermosetting material, and is an indicator of the degree of thermosetting. That is, it can be said that the lower the acetone extraction rate, the smaller the proportion of uncured thermosetting composition and the higher the degree of thermosetting.
  • the acetone extraction rate it is possible to detect a trace amount of uncured thermosetting composition of 1.1% by mass or less, and to evaluate the degree of thermosetting with high sensitivity.
  • the degree of thermosetting can be further increased, and it becomes easier to obtain a thermoset having excellent mechanical properties.
  • the acetone extraction rate is more preferably 1.1% by mass or less, and even more preferably 1.0% by mass or less.
  • the lower limit of the acetone extraction rate is not particularly limited, and the lower the better.
  • the heat curing of the thermosetting composition is performed as follows by the spectrum intensity ratio determined by the ATR (Attenuated Total Reflection) method by FT-IR (Fourier Transform Infrared Spectroscopy). degree can be evaluated.
  • the intensity ratio I CN /ICO between the intensity I CN derived from and the intensity I CO derived from the CO single bond at 1250 cm ⁇ 1 obtained by drawing the baseline at 1280 cm ⁇ 1 to 1200 cm ⁇ 1 is 0.036. The following are preferable.
  • the intensity ICO is the intensity of the peak derived from the CO single bond of the main agent, and is the reference intensity at which the amount of substance does not change before and after heat curing.
  • the intensity I CN is a peak derived from the CN triple bond of dicyandiamide, and decreases as the CN triple bond is consumed as the heat curing progresses.
  • the intensity ratio I CN /I CO corresponds to the residual proportion of unreacted CN triple bonds and is an index of the degree of thermosetting. That is, it can be said that the lower the strength ratio I CN / ICO is, the smaller the ratio of remaining unreacted CN triple bonds is, and the higher the degree of thermosetting.
  • the intensity ratio I CN /I CO is more preferably 0.033 or less, even more preferably 0.030 or less.
  • the lower limit of the intensity ratio I CN /I CO is not particularly limited, and the lower the better.
  • the coefficient of variation obtained by dividing the standard deviation by the average value is preferably 0.225 or less.
  • the standard deviation and average value are obtained by collecting samples from five randomly selected locations of the thermosetting material obtained by thermally curing the thermosetting composition at 150 ° C. for 30 minutes, and the acetone extraction solution obtained from each sample. It is calculated from the intensity ratio I CN / ICO .
  • the coefficient of variation is more preferably 0.22 or less, even more preferably 0.215 or less.
  • thermosetting composition contains a curing accelerator, core-shell type rubber, glass fiber, carbon fiber, carbon nanotube, carbon nanofiber, antifoaming agent, plasticizer, pigment, leveling agent, surfactant, oxidizing Inhibitors, UV absorbers, and the like may be included. Each of these components may be used singly or in combination of two or more.
  • curing accelerators examples include 3-(3,4-dichlorophenyl)-1,1-dimethylurea, phosphine compounds, imidazole compounds, quaternary ammonium salts, and tertiary amines. From the viewpoint of thermosetting, the curing accelerator preferably contains 3-(3,4-dichlorophenyl)-1,1-dimethylurea.
  • the content of the curing accelerator is not particularly limited, and may be appropriately set in consideration of the application.
  • core-shell type rubber include acryl-butadiene core-shell rubber.
  • ductility can be imparted to the resulting thermoset.
  • the thermosetting composition has a particle size of 40 ⁇ m or less before being heat-cured, the inclusion of the acryl-butadiene core-shell rubber can more preferably exhibit ductility.
  • thermosetting composition ⁇ Method for producing thermosetting composition>
  • the method for producing the thermosetting composition according to the present disclosure is not particularly limited, the following method for producing the thermosetting composition according to the present disclosure can be suitably used.
  • a method for producing a thermosetting composition according to the present disclosure includes a step of dispersing a mixture containing a main agent having a glycidyl ether group and a solid latent curing agent with three rolls. By dispersing the mixture using three rolls, it becomes easy to make the particle size 40 ⁇ m or less before heat curing. Thereby, a thermosetting composition according to the present disclosure can be produced.
  • the mixture may contain the above other components in addition to the main agent and the latent curing agent.
  • the details of the main agent, latent curing agent and other components are as described above.
  • thermosetting composition A mixture was prepared by mixing the following main agent, latent curing agent, curing accelerator and additive (core-shell type rubber).
  • Comparative Example 1 A mixture prepared in the same manner as in Example 1 was stirred at 30° C. for 5 minutes using a planetary mixer. Thus, a thermosetting composition of Comparative Example 1 was produced.
  • Comparative Example 2 A mixture prepared in the same manner as in Example 1 was stirred at 10° C. for 90 minutes using a planetary mixer. Thus, a thermosetting composition of Comparative Example 2 was produced.
  • thermoset ⁇ Preparation of thermoset>
  • the thermosetting composition is poured into a molding jig (two aluminum plates coated with Teflon (registered trademark) are stacked via a 4 mm thick spacer) and heat cured in a constant temperature bath at 150°C for 30 minutes.
  • a plate-shaped thermoset material having a thickness of 4 mm was obtained.
  • thermosetting composition and thermoset > Particle size, viscosity, acetone extraction rate, strength ratio I CN /I CO , coefficient of variation, tensile strength, elongation at break, and flexural modulus were evaluated for the thermosetting composition and thermoset according to the following procedures.
  • the particle size was measured by the grain gauge (grind gauge) method according to JIS K 5600-2-5:1999.
  • thermosetting composition Using an E-type viscometer (“TV-25 type” manufactured by Toki Sangyo Co., Ltd.), the viscosity of the thermosetting composition at 25° C. was measured.
  • the acetone extraction rate was calculated for five samples, and the average value thereof was taken as the acetone extraction rate of the thermoset. [Spectral intensity ratio] Acetone extracts were obtained for the five samples in a manner similar to that described above for acetone extractability.
  • the acetone extract was analyzed by the ATR method by FT-IR using a diamond crystal to obtain a spectroscopic spectrum.
  • the intensity I CN derived from the CN triple bond at 2200 cm -1 obtained by drawing a baseline at 2260 cm -1 to 2120 cm -1 and the baseline at 1280 cm -1 to 1200 cm -1
  • the intensity ratio I CN /I CO with the intensity I CO derived from the resulting 1250 cm ⁇ 1 CO single bond was calculated.
  • the intensity ratio I CN / ICO was calculated for the five acetone extracts, and the average value thereof was taken as the intensity ratio I CN / ICO of the thermoset. [Coefficient of variation] Using the intensity ratio I CN /I CO obtained from the five acetone extracts described above, the standard deviation was calculated and the coefficient of variation was calculated by dividing the standard deviation by the mean.
  • thermoset The tensile strength and elongation at break of the thermoset were measured by performing a tensile test according to JIS K 7238-2:2009.
  • the flexural modulus of the thermoset was measured by performing a flexural test according to JIS K 7238-2:2009. Also, in the bending test, the presence or absence of cracks in the thermoset was confirmed.
  • Table 1 shows the above evaluation results.
  • thermosetting composition of Example 1 While achieving tensile strength and flexural modulus equivalent to those of Comparative Examples 1 and 2, the elongation at break is superior, and cracking is suppressed. It was possible to obtain a product, that is, a thermoset product with excellent mechanical properties.
  • thermosetting composition since the particle size of the thermosetting composition was large, the elongation at break of the thermoset was small, and the thermoset was cracked in the bending test, resulting in poor mechanical properties.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition thermodurcissable comprenant un agent principal avec un groupe éther glycidylique, et un agent de durcissement latent solide, la taille des particules avant durcissement thermique étant inférieure ou égale à 40 µm.
PCT/JP2022/032494 2021-09-01 2022-08-30 Composition thermodurcissable Ceased WO2023032943A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE112022003178.6T DE112022003178T5 (de) 2021-09-01 2022-08-30 Unter Wärme aushärtbare Zusammensetzung

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021-142713 2021-09-01
JP2021142713A JP2023035684A (ja) 2021-09-01 2021-09-01 熱硬化性組成物

Publications (1)

Publication Number Publication Date
WO2023032943A1 true WO2023032943A1 (fr) 2023-03-09

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PCT/JP2022/032494 Ceased WO2023032943A1 (fr) 2021-09-01 2022-08-30 Composition thermodurcissable

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JP (1) JP2023035684A (fr)
DE (1) DE112022003178T5 (fr)
WO (1) WO2023032943A1 (fr)

Citations (10)

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JPS6096617A (ja) * 1983-10-31 1985-05-30 Asahi Chem Ind Co Ltd エポキシ樹脂の硬化方法
JPS60124618A (ja) * 1983-11-11 1985-07-03 エス・カー・ヴエー・トローストベルク・アクチエンゲゼルシャフト ポキシ樹脂コンパウンド用硬化剤およびその製造法
JPS6134019A (ja) * 1984-07-25 1986-02-18 Matsushita Electric Works Ltd 封止用樹脂組成物の製法
JPH0616788A (ja) * 1991-05-20 1994-01-25 Nitto Denko Corp 微粒子状硬化剤または微粒子状硬化促進剤、およびそれを含有してなるエポキシ樹脂組成物、並びに硬化方法
JPH11209580A (ja) * 1998-01-27 1999-08-03 Matsushita Electric Works Ltd エポキシ樹脂組成物及びその製造方法及びプリプレグの製造方法
JP2005239922A (ja) * 2004-02-27 2005-09-08 Taoka Chem Co Ltd 一液型液状エポキシ樹脂組成物
JP2011157491A (ja) * 2010-02-02 2011-08-18 Toray Ind Inc トウプリプレグ用エポキシ樹脂組成物およびトウプリプレグ
WO2017099060A1 (fr) * 2015-12-10 2017-06-15 三菱レイヨン株式会社 Préimprégné de câble, et récipient sous pression renforcé par un matériau composite ainsi que procédé de fabrication de celui-ci
JP2018532014A (ja) * 2015-10-13 2018-11-01 ダウ グローバル テクノロジーズ エルエルシー 高スループット製造プロセスでの使用のための速硬化性エポキシ組成物
WO2019065663A1 (fr) * 2017-09-29 2019-04-04 日鉄ケミカル＆マテリアル株式会社 Composition de résine durcissable et faisceau de fibres pré-imprégné l'utilisant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
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JPH07224144A (ja) * 1994-02-07 1995-08-22 Nippon Zeon Co Ltd エポキシ樹脂系接着性組成物の製造方法
JP2011069653A (ja) 2009-09-24 2011-04-07 Panasonic Electric Works Co Ltd エポキシ樹脂含有材料の硬化度評価方法
JP6063367B2 (ja) 2012-12-04 2017-01-18 本田技研工業株式会社 エポキシ樹脂の混練分散性評価方法

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6096617A (ja) * 1983-10-31 1985-05-30 Asahi Chem Ind Co Ltd エポキシ樹脂の硬化方法
JPS60124618A (ja) * 1983-11-11 1985-07-03 エス・カー・ヴエー・トローストベルク・アクチエンゲゼルシャフト ポキシ樹脂コンパウンド用硬化剤およびその製造法
JPS6134019A (ja) * 1984-07-25 1986-02-18 Matsushita Electric Works Ltd 封止用樹脂組成物の製法
JPH0616788A (ja) * 1991-05-20 1994-01-25 Nitto Denko Corp 微粒子状硬化剤または微粒子状硬化促進剤、およびそれを含有してなるエポキシ樹脂組成物、並びに硬化方法
JPH11209580A (ja) * 1998-01-27 1999-08-03 Matsushita Electric Works Ltd エポキシ樹脂組成物及びその製造方法及びプリプレグの製造方法
JP2005239922A (ja) * 2004-02-27 2005-09-08 Taoka Chem Co Ltd 一液型液状エポキシ樹脂組成物
JP2011157491A (ja) * 2010-02-02 2011-08-18 Toray Ind Inc トウプリプレグ用エポキシ樹脂組成物およびトウプリプレグ
JP2018532014A (ja) * 2015-10-13 2018-11-01 ダウ グローバル テクノロジーズ エルエルシー 高スループット製造プロセスでの使用のための速硬化性エポキシ組成物
WO2017099060A1 (fr) * 2015-12-10 2017-06-15 三菱レイヨン株式会社 Préimprégné de câble, et récipient sous pression renforcé par un matériau composite ainsi que procédé de fabrication de celui-ci
WO2019065663A1 (fr) * 2017-09-29 2019-04-04 日鉄ケミカル＆マテリアル株式会社 Composition de résine durcissable et faisceau de fibres pré-imprégné l'utilisant

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DE112022003178T5 (de) 2024-04-18

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