JP2013536883A - 改善された機械的特性、特に、高められた破断伸びを有するポリメタクリルイミドフォーム - Google Patents
改善された機械的特性、特に、高められた破断伸びを有するポリメタクリルイミドフォーム Download PDFInfo
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- JP2013536883A JP2013536883A JP2013526376A JP2013526376A JP2013536883A JP 2013536883 A JP2013536883 A JP 2013536883A JP 2013526376 A JP2013526376 A JP 2013526376A JP 2013526376 A JP2013526376 A JP 2013526376A JP 2013536883 A JP2013536883 A JP 2013536883A
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- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
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- 229910052749 magnesium Inorganic materials 0.000 description 2
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- ZHQXMHOJBJSNGB-UHFFFAOYSA-N carbonic acid;2-hydroxy-2-methylpropanenitrile Chemical compound OC(O)=O.CC(C)(O)C#N ZHQXMHOJBJSNGB-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- BLCKNMAZFRMCJJ-UHFFFAOYSA-N cyclohexyl cyclohexyloxycarbonyloxy carbonate Chemical compound C1CCCCC1OC(=O)OOC(=O)OC1CCCCC1 BLCKNMAZFRMCJJ-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- CGBYBGVMDAPUIH-ARJAWSKDSA-N dimethylmaleic acid Chemical compound OC(=O)C(/C)=C(/C)C(O)=O CGBYBGVMDAPUIH-ARJAWSKDSA-N 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GZXSDYYWLZERLF-UHFFFAOYSA-N ethyl n-ethylcarbamate Chemical compound CCNC(=O)OCC GZXSDYYWLZERLF-UHFFFAOYSA-N 0.000 description 1
- CUICPJOPYVMUPK-UHFFFAOYSA-N ethyl n-tert-butylcarbamate Chemical compound CCOC(=O)NC(C)(C)C CUICPJOPYVMUPK-UHFFFAOYSA-N 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- DUVTXUGBACWHBP-UHFFFAOYSA-N methyl 2-(1h-benzimidazol-2-ylmethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCC1=NC2=CC=CC=C2N1 DUVTXUGBACWHBP-UHFFFAOYSA-N 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
- CNPHCSFIDKZQAK-UHFFFAOYSA-N n-prop-2-enylprop-2-enamide Chemical compound C=CCNC(=O)C=C CNPHCSFIDKZQAK-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005385 peroxodisulfate group Chemical group 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000004616 structural foam Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- KQYLUTYUZIVHND-UHFFFAOYSA-N tert-butyl 2,2-dimethyloctaneperoxoate Chemical compound CCCCCCC(C)(C)C(=O)OOC(C)(C)C KQYLUTYUZIVHND-UHFFFAOYSA-N 0.000 description 1
- MRETXWVWJPDBKQ-UHFFFAOYSA-N tetraethyl methanetetracarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)(C(=O)OCC)C(=O)OCC MRETXWVWJPDBKQ-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- AGZPNUZBDCYTBB-UHFFFAOYSA-N triethyl methanetricarboxylate Chemical compound CCOC(=O)C(C(=O)OCC)C(=O)OCC AGZPNUZBDCYTBB-UHFFFAOYSA-N 0.000 description 1
- BNOIMFITGLLJTH-UHFFFAOYSA-N trimethyl methanetricarboxylate Chemical compound COC(=O)C(C(=O)OC)C(=O)OC BNOIMFITGLLJTH-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical class [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
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- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B5/00—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts
- B32B5/18—Layered products characterised by the non- homogeneity or physical structure, i.e. comprising a fibrous, filamentary, particulate or foam layer; Layered products characterised by having a layer differing constitutionally or physically in different parts characterised by features of a layer of foamed material
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/52—Amides or imides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/42—Nitriles
- C08F220/44—Acrylonitrile
- C08F220/46—Acrylonitrile with carboxylic acids, sulfonic acids or salts thereof
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/04—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent
- C08J9/12—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent
- C08J9/14—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof using blowing gases generated by a previously added blowing agent by a physical blowing agent organic
- C08J9/142—Compounds containing oxygen but no halogen atom
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2250/00—Layers arrangement
- B32B2250/03—3 layers
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- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2266/00—Composition of foam
- B32B2266/02—Organic
- B32B2266/0214—Materials belonging to B32B27/00
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- C08J2333/18—Homopolymers or copolymers of nitriles
- C08J2333/20—Homopolymers or copolymers of acrylonitrile
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Abstract
Description
PMIフォーム、例えばEvonik Roehm社のROHACELL(登録商標)は、ストラクチュラルフォームとして複合物に使用され、そのためには繊維、多くの場合炭素繊維もしくはガラス繊維と樹脂とからなるカバー層と一緒に加工される。前記複合物の構成が、多くの場合180℃の温度で行われる一方、その構成部材は−55℃の温度でも使用される。前記カバー層およびPMIフォームの異なる熱膨張率(CTE)によって、冷却時に亀裂がコア部に生じ、これはこのような構成部材でのPMIフォームの使用に対する1つの除外基準である。一般に、航空機産業の相応の試験に合格しない。したがって、加工を行う産業、例えば航空機および宇宙産業において、しかし道路車両または鉄道車両のメーカーでも、改善された破断伸びを有するフォーム材料に高い関心が持たれている。
したがって、本発明の課題は、特に高い破断強度を有するPMIフォーム材の製造のための配合物を見出すことであった。このフォーム材はさらに、公知のPMIフォームと同様に優れた、またはさらに改善された熱機械的特性を有するものである。
前記課題は、発泡性の架橋されたポリマー、特にPMIフォームの新しい製造方法によって解決され、この方法では、前記ポリマーは、(メタ)アクリル酸、(メタ)アクリロニトリル、および少なくとも250g/molの分子量を有するジオールの(メタ)アクリル酸ジエステルを含んでいる。
・密度が30〜300kg/m3の所望の範囲にある微孔性のPMIフォームが得られる。
・所望の高い破断伸びは、−60℃〜200℃の幅広い温度範囲において保証されている。
・重合のためには、工業的に容易な方法で製造でき、かつさらなる加工ができる、均質で流動性の混合物が使用される。
・破断伸び、耐熱保形性およびクリープ挙動以外のその他の機械的特性は、商業的に入手可能な製品におけるよりも明らかに優れている。
破断伸びおよび破断強度を、引張試験を用いてISO527−2に準拠して測定した。
密度をISO845に準拠して測定する。
耐熱保形性をDIN53424に準拠して測定した。
クリープ挙動(クリープ)を、DIN53425、ASTM D621およびD2990にしたがい、180℃、2時間の測定時間かつ0.7MPaの圧力にて測定した。
メタクリル酸2487g、メタクリロニトリル2538g、およびtert−ブチルメタクリレート102gからなる混合物に、発泡剤としてtert−ブタノール355gを添加した。さらに、この混合物にtert−ブチルペルピバレート2g、tert−ブチルペル−2−エチルヘキサノエート1.8g、tert−ブチルペルベンゾエート5.1g、クミルペルネオデカノエート5.2g、酸化マグネシウム11.2gおよび離型剤(Moldwiz INT 20E)15.2gを添加した。架橋剤として、ポリエチレングリコール400のメタクリル酸ジエステル77.2gを添加した。
メタクリル酸2421g、メタクリロニトリル2471gからなる混合物に、発泡剤としてtert−ブタノール593gを添加した。さらに、この混合物にtert−ブチルペルピバレート2g、tert−ブチルペル−2−エチルヘキサノエート1.8g、tert−ブチルペルベンゾエート4.9g、クミルペルネオデカノエート5.1g、酸化マグネシウム10.9gおよび離型剤(Moldwiz INT 20E)14.8gを添加した。架橋剤として、ポリエチレングリコール400のメタクリル酸ジエステル75.1gを添加した。
メタクリル酸2379g、メタクリロニトリル2428g、およびtert−ブチルメタクリレート97gからなる混合物に、発泡剤としてtert−ブタノール340gを添加した。さらに、この混合物にtert−ブチルペルピバレート1.9g、tert−ブチルペル−2−エチルヘキサノエート1.8g、tert−ブチルペルベンゾエート4.8g、クミルペルネオデカノエート5.0g、酸化マグネシウム10.7gおよび離型剤(Moldwiz INT 20E)14.5gを添加した。架橋剤として、ポリエチレングリコール400のメタクリル酸ジエステル73.8gを添加した。
メタクリル酸2520g、メタクリロニトリル2572g、およびtert−ブチルメタクリレート103gからなる混合物に、発泡剤としてtert−ブタノール360gを添加した。さらに、この混合物にtert−ブチルペルピバレート2.1g、tert−ブチルペル−2−エチルヘキサノエート1.9g、tert−ブチルペルベンゾエート5.1g、クミルペルネオデカノエート5.3g、酸化マグネシウム10.3gおよび離型剤(Moldwiz INT 20E)15.4gを添加した。架橋剤として、アリルメタクリレート5.1gを添加した。
Claims (9)
- 発泡性の架橋されたポリマーの製造方法において、前記ポリマーが(メタ)アクリル酸、(メタ)アクリロニトリル、および少なくとも250g/molの分子量を有するジオールの(メタ)アクリル酸ジエステルを含んでいることを特徴とする前記方法。
- 請求項1に記載の発泡性の架橋されたポリマーの製造方法において、
(A)(メタ)アクリル酸30〜70質量%、
(メタ)アクリロニトリル30〜60質量%、
さらなるビニル性不飽和モノマー0〜35質量%、
(B)少なくとも250g/molの分子量を有するジオールの(メタ)アクリル酸ジエステル0.01〜15質量%、
(C)発泡剤0.01〜15質量%、
(D)さらなる架橋剤0〜10質量%、
(E)重合開始剤0.01〜2.0質量%、および
(F)通常の添加剤0〜20質量%
からなる混合物を、塊状重合させて板状にすることを特徴とする前記方法。 - 請求項2に記載の発泡性の架橋されたポリマーの製造方法において、前記ジオールが、ポリエーテルジオール、ポリエステルジオール、両末端官能性オリゴ(メタ)アクリレートまたはポリオレフィンジオールであり、好ましくはポリエーテルジオールであることを特徴とする前記方法。
- 請求項2または3に記載の発泡性の架橋されたポリマーの製造方法において、
(A)メタクリル酸30〜70質量%、
メタクリロニトリル30〜60質量%、
さらなるビニル性不飽和モノマー0〜30質量%、
(B)250〜1500g/molの分子量を有するジオールのメタクリル酸ジエステル0.01〜15質量%、
(C)発泡剤0.01〜15質量%、
(D)さらなる架橋剤0.01〜10質量%、
(E)重合開始剤0.01〜2.0質量%および
(F)通常の添加剤0〜20質量%
からなる混合物を、塊状重合させて板状にすることを特徴とする前記方法。 - 請求項1から4までのいずれか1項に記載の発泡性の架橋されたポリマーの製造方法において、前記混合物を塊状重合させて板状にし、場合により熱処理して、引き続き150〜250℃の温度にて発泡させることを特徴とする前記方法。
- 請求項1から4までのいずれか1項に記載の方法により製造されたポリマーの発泡によって得られることを特徴とするポリ(メタ)アクリルイミドフォーム材。
- 7.0%よりも大きい、特に9.0%よりも大きい破断伸びを有することを特徴とする、請求項6に記載のポリ(メタ)アクリルイミドフォーム材。
- 請求項6または7に記載のポリ(メタ)アクリルイミドフォーム材の層を含んでいる積層材料。
- 請求項6から8までのいずれか1項に記載のポリ(メタ)アクリルイミドフォーム材から部分的になることを特徴とする、チューブ、スピーカー、アンテナ、X線透視台、機械部品、自動車、鉄道車両、船舶、航空機、宇宙船。
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PCT/EP2011/060888 WO2012028353A1 (de) | 2010-08-31 | 2011-06-29 | Pmi-schäume mit verbesserten mechanischen eigenschaften, insbesondere mit erhöhter reissdehnung |
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DE102011085026A1 (de) | 2011-10-21 | 2013-04-25 | Evonik Röhm Gmbh | Verfahren zur Herstellung von Korngrenzenhaftung von expandierten Copolymeren auf Basis von Methacryl- und Acrylverbindungen und Anhaftung diverser Deckschichten auf dem Schaumkern |
CA2879927C (en) | 2012-07-24 | 2021-01-26 | Evonik Industries Ag | Novel shaping process for pmi foam materials and/or composite components produced therefrom |
EP3144344A1 (de) | 2015-09-15 | 2017-03-22 | Evonik Röhm GmbH | Mehrfunktionale alkohole als vernetzer in pmi schaumstoffen |
EP3463794A1 (de) * | 2016-05-25 | 2019-04-10 | Basf Se | Konfektionierung faserverstärkter schaumstoffe |
RU182764U1 (ru) * | 2018-06-06 | 2018-08-30 | Роман Юрьевич Бартош | Композитный функциональный материал |
CN109265597A (zh) * | 2018-06-29 | 2019-01-25 | 中国科学院上海有机化学研究所 | 一种低成本聚甲基丙烯酰亚胺泡沫塑料及其制备方法 |
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CN111363085B (zh) * | 2020-04-24 | 2022-04-05 | 维赛(江苏)复合材料科技有限公司 | 一种耐高温单甲基聚甲基丙烯酰亚胺结构泡沫及其制备方法 |
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CN116554388A (zh) * | 2023-05-31 | 2023-08-08 | 保定美沃工程材料科技有限公司 | 一种耐超高温的pmi泡沫塑料 |
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TWI525144B (zh) | 2016-03-11 |
SG187925A1 (en) | 2013-03-28 |
RU2013114180A (ru) | 2014-10-10 |
DE102010040286A1 (de) | 2012-03-01 |
DK2611857T3 (en) | 2014-12-15 |
US9212269B2 (en) | 2015-12-15 |
EP2611857A1 (de) | 2013-07-10 |
IL222864A0 (en) | 2012-12-31 |
WO2012028353A1 (de) | 2012-03-08 |
KR20130103493A (ko) | 2013-09-23 |
TW201224040A (en) | 2012-06-16 |
PL2611857T3 (pl) | 2015-03-31 |
KR101847668B1 (ko) | 2018-04-10 |
ES2525164T3 (es) | 2014-12-18 |
JP5905008B2 (ja) | 2016-04-20 |
JP6192691B2 (ja) | 2017-09-06 |
RU2591963C2 (ru) | 2016-07-20 |
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