JP2010530908A - エポキシドの硬化のための触媒 - Google Patents
エポキシドの硬化のための触媒 Download PDFInfo
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- JP2010530908A JP2010530908A JP2010511597A JP2010511597A JP2010530908A JP 2010530908 A JP2010530908 A JP 2010530908A JP 2010511597 A JP2010511597 A JP 2010511597A JP 2010511597 A JP2010511597 A JP 2010511597A JP 2010530908 A JP2010530908 A JP 2010530908A
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- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 125000000962 organic group Chemical group 0.000 claims abstract description 20
- 150000001450 anions Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 7
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- 239000004831 Hot glue Substances 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 1
- TVTPFWIMEPZIDB-UHFFFAOYSA-N OB(O)O.C1=CN=CN1.C1=CN=CN1.C1=CN=CN1 Chemical class OB(O)O.C1=CN=CN1.C1=CN=CN1.C1=CN=CN1 TVTPFWIMEPZIDB-UHFFFAOYSA-N 0.000 description 1
- XPFRXWCVYUEORT-UHFFFAOYSA-N Phenacemide Chemical compound NC(=O)NC(=O)CC1=CC=CC=C1 XPFRXWCVYUEORT-UHFFFAOYSA-N 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920002732 Polyanhydride Polymers 0.000 description 1
- 229920002873 Polyethylenimine Polymers 0.000 description 1
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 description 1
- QLBRROYTTDFLDX-UHFFFAOYSA-N [3-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCCC(CN)C1 QLBRROYTTDFLDX-UHFFFAOYSA-N 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- IMUDHTPIFIBORV-UHFFFAOYSA-N aminoethylpiperazine Chemical compound NCCN1CCNCC1 IMUDHTPIFIBORV-UHFFFAOYSA-N 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- XMSVKICKONKVNM-UHFFFAOYSA-N bicyclo[2.2.1]heptane-3,4-diamine Chemical compound C1CC2(N)C(N)CC1C2 XMSVKICKONKVNM-UHFFFAOYSA-N 0.000 description 1
- 150000001642 boronic acid derivatives Chemical class 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- QVKQJEWZVQFGIY-UHFFFAOYSA-N dipropyl hydrogen phosphate Chemical compound CCCOP(O)(=O)OCCC QVKQJEWZVQFGIY-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000012990 dithiocarbamate Substances 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- 229940005631 hypophosphite ion Drugs 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 229960003396 phenacemide Drugs 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical compound [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000962 poly(amidoamine) Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VOZKAJLKRJDJLL-UHFFFAOYSA-N tolylenediamine group Chemical group CC1=C(C=C(C=C1)N)N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
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
- C08G59/68—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
-
- 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
- C08G59/688—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 phosphorus
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/249921—Web or sheet containing structurally defined element or component
- Y10T428/249924—Noninterengaged fiber-containing paper-free web or sheet which is not of specified porosity
- Y10T428/24994—Fiber embedded in or on the surface of a polymeric matrix
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
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)
- Adhesives Or Adhesive Processes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
Abstract
Description
R1及びR3は、相互に無関係に、1〜20個のC原子を有する有機基を表し、
R2、R4及びR5は、相互に無関係に、H原子又は1〜20個のC原子を有する有機基を表し、その際、R4及びR5は一緒になって脂肪族環又は芳香環を形成することもでき、かつ、
Xは、リンの酸素酸のアニオンを表し、かつ、
nは1、2又は3を表す]
の1,3置換イミダゾリウム塩の使用に関する。
本発明によれば、式I
R1及びR3は、相互に無関係に、1〜20個のC原子を有する有機基を表し、
R2、R4及びR5は、相互に無関係に、H原子、又は、1〜20個のC原子、特に1〜10個のC原子を有する有機基を表し、その際、R4及びR5は一緒になって脂肪族環又は芳香環を形成することもでき、かつ、
Xは、リンの酸素酸のアニオンを表し、かつ、
nは1、2又は3を表す]
の1,3置換イミダゾリウム塩が使用される。
R1及びR3はメチル基を表す、
R1及びR3はエチル基を表す、
R1はメチル基を表し、かつR3はエチル基を表す、
R1はメチル基を表し、かつR3はnプロピル基を表す、
R1はメチル基を表し、かつR3はnブチル基を表す、
R1はメチル基を表し、かつR3はアリル基を表す、
R1はエチル基を表し、かつR3はアリル基を表す、
R1はメチル基を表し、かつR3はベンジル基を表す、
R1はエチル基を表し、かつR3はベンジル基を表す。
R2、R4及びR5はH原子を表し、
R2は、H原子又はC1〜C4アルキル基を表し、かつR4及びR5は、H原子又はC1〜C4アルキル基を表す。
1−ブチル−3−メチル−イミダゾリウム(R1=ブチル、R3=メチル)
1−ブチル−3−エチル−イミダゾリウム(R1=ブチル、R3=エチル)
1,3−ジ−メチル−イミダゾリウム(R1=メチル、R3=メチル)
1−エチル−3−メチル−イミダゾリウム(R1=エチル、R3=メチル)
1−エチル−2,3ジメチルイミダゾリウム(R1=エチル、R2=メチル、R3=メチル)。
硬化性組成物はエポキシ化合物を含有する。特に、1〜10個のエポキシ基、有利に少なくとも2個のエポキシ基を有するエポキシ化合物が該当する。
本発明による組成物は、潜在性触媒及びエポキシ化合物に加えて、他の成分を含有してよい。
式Iのイミダゾリウム塩を含有する組成物は、貯蔵安定性である。式Iのイミダゾリウム塩は、エポキシ化合物中及び本発明による組成物で十分に可溶性である。式Iのイミダゾリウム塩は、組成物中で潜在性触媒として作用する。前記塩の、エポキシ化合物の重合又は架橋の際の有効性は極めて良好である。
エポキシ化合物として、Nan Ya社からNPEL 127Hの名称で市販品として入手可能なビスフェノールAのジグリシジルエーテル(DGEBAと略記)を使用した。
それぞれイミダゾリウム塩又はイミダゾリウム塩の混合物5質量部とエポキシ化合物100質量部とを混合した。第1表に、組成及び結果を列挙する。1X及び1XXの場合、他の成分との混合物も試験した(第2表の下方の脚注を参照のこと)。
硬化の開始及び進行を、示差走査熱量測定(DSC)を用いて試験した。そのために、組成物5〜15ミリグラムを、DSC熱量計(DSC 822, Mettler Toledo)中で、10℃/分の一定速度で加熱した。
未硬化の組成物20gを3〜4mmのフィルム厚でアルミニウムボートに入れ、160℃で1時間、次いで180℃でさらに3時間、次いで200℃でさらに1時間硬化させた。硬化した試料のTgを、DSC測定により、30℃/分の加熱速度で、3つの無関係な測定の平均値として測定した。
モル比 エポキシド:無水物 1:0.9
エポキシド100質量部に対してイミダゾリウム塩1質量部
硬化条件:100℃で3時間、及び150℃で2時間
モル比 エポキシド:ヒドロキシ 1:0.9
エポキシド+Novolak100質量部に対してイミダゾリウム塩1質量部
硬化条件:140℃で2時間、及び100℃で2時間
Claims (21)
- R1及びR3が、相互に無関係に、C1〜C10アルキル基、アリル基又はベンジル基を表す、請求項1記載の使用。
- R2、R4及びR5が、相互に無関係に、H原子又はC1〜C8アルキル基、C1〜C8アルケニル基、特にアリル基、フェニル基又はベンジル基を表す、請求項1又は2記載の使用。
- R2がH原子を表す、請求項1から3までのいずれか1項記載の使用。
- アニオンXが、1〜20個のC原子を有する少なくとも1の有機基を含有する、請求項1から4までのいずれか1項記載の使用。
- アニオンXがジアルキルリン酸イオンである、請求項1から5までのいずれか1項記載の使用。
- nが1を表す、請求項1から6までのいずれか1項記載の使用。
- 硬化性組成物が、少なくとも2のエポキシ基を有するエポキシ化合物を含有する、請求項1から7までのいずれか1項記載の使用。
- 硬化性組成物が、平均で2のエポキシ基を有するエポキシ化合物を含有する、請求項1から8までのいずれか1項記載の使用。
- 組成物が、エピクロロヒドリンとアルコールとの反応により得られるエポキシ化合物を含有する、請求項1から9までのいずれか1項記載の使用。
- 組成物が、水及び有機溶剤を除いて、少なくとも30質量%、有利に少なくとも50質量%がエポキシ化合物からなる、請求項1から10までのいずれか1項記載の使用。
- 組成物が、更に、他の成分、例えば無水物硬化剤又はフェノール樹脂、特にノボラックを含有する、請求項1から11までのいずれか1項記載の使用。
- 潜在性触媒の含分が、エポキシ化合物100質量部に対して0.01〜10質量部である、請求項1から12までのいずれか1項記載の使用。
- エポキシ化合物及び式Iの潜在性触媒を含有する、硬化性組成物。
- DICY及び/又はアミン架橋剤を含有する、請求項14記載の硬化性組成物。
- 窒素含有成分を硬化剤として含有する、請求項14又は15記載の硬化性組成物。
- イミダゾリウム塩中のDICYの、室温で液体でありかつ均質な混合物を含有する、請求項16記載の硬化性組成物。
- 水及び有機溶剤を除いて、少なくとも30質量%がエポキシ化合物からなる、請求項14から17までのいずれか1項記載の硬化性組成物。
- 請求項14から17までのいずれか1項記載の組成物を硬化するための方法において、硬化を200℃未満の温度で行うことを特徴とする方法。
- 被覆剤又は含浸剤としての、接着剤としての、複合材における、成形体を製造するための、又は、成形体の埋込み、結合又は固化のための注型材料としての、請求項14から17までのいずれか1項記載の硬化性組成物の使用。
- 予備含浸された繊維又は繊維織物の硬化により、又は、押出、引抜成形、巻取り及びレジントランスファ成形、レジンインフュージョン技術により複合材を製造するための、請求項14から17までのいずれか1項記載の硬化性組成物の使用。
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PCT/EP2008/057115 WO2008152002A1 (de) | 2007-06-14 | 2008-06-06 | Katalysator für die härtung von epoxiden |
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JP2014181257A (ja) * | 2013-03-18 | 2014-09-29 | Sekisui Chem Co Ltd | 熱硬化性樹脂組成物、及び、半導体装置の製造方法 |
US9018321B2 (en) | 2007-07-26 | 2015-04-28 | Ajinomoto Co., Inc. | Resin composition |
JP2017506175A (ja) * | 2014-02-19 | 2017-03-02 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | 巻成品のコーティング方法及び装置 |
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EP2158251B1 (de) | 2007-06-12 | 2012-11-28 | Basf Se | Katalysator für die härtung von epoxiden |
JP5377990B2 (ja) * | 2009-01-26 | 2013-12-25 | 株式会社ティ−アンドケイ東華 | 液状の潜在性硬化剤組成物及び一液性の硬化性エポキシド組成物 |
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- 2008-06-06 EP EP20080760685 patent/EP2158250B1/de active Active
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WO2008152002A1 (de) | 2008-12-18 |
US20100166971A1 (en) | 2010-07-01 |
CN101687977A (zh) | 2010-03-31 |
KR20100044171A (ko) | 2010-04-29 |
KR101438867B1 (ko) | 2014-09-11 |
TW200906889A (en) | 2009-02-16 |
CN101687977B (zh) | 2012-08-15 |
JP5260639B2 (ja) | 2013-08-14 |
TWI426091B (zh) | 2014-02-11 |
EP2158250A1 (de) | 2010-03-03 |
ATE531746T1 (de) | 2011-11-15 |
EP2158250B1 (de) | 2011-11-02 |
US8202580B2 (en) | 2012-06-19 |
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