JP5847078B2 - テレフタル酸単位ならびにトリメチルヘキサメチレンジアミン単位を含有するコポリアミドをベースとする成形材料 - Google Patents
テレフタル酸単位ならびにトリメチルヘキサメチレンジアミン単位を含有するコポリアミドをベースとする成形材料 Download PDFInfo
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- JP5847078B2 JP5847078B2 JP2012518992A JP2012518992A JP5847078B2 JP 5847078 B2 JP5847078 B2 JP 5847078B2 JP 2012518992 A JP2012518992 A JP 2012518992A JP 2012518992 A JP2012518992 A JP 2012518992A JP 5847078 B2 JP5847078 B2 JP 5847078B2
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- terephthalic acid
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N terephthalic acid group Chemical group C(C1=CC=C(C(=O)O)C=C1)(=O)O KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims description 39
- 239000012778 molding material Substances 0.000 title claims description 26
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical group CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 title description 10
- 239000000835 fiber Substances 0.000 claims description 20
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- 239000000843 powder Substances 0.000 claims description 16
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- 239000000178 monomer Substances 0.000 claims description 8
- YQLZOAVZWJBZSY-UHFFFAOYSA-N decane-1,10-diamine Chemical compound NCCCCCCCCCCN YQLZOAVZWJBZSY-UHFFFAOYSA-N 0.000 claims description 6
- JCUZDQXWVYNXHD-UHFFFAOYSA-N 2,2,4-trimethylhexane-1,6-diamine Chemical compound NCCC(C)CC(C)(C)CN JCUZDQXWVYNXHD-UHFFFAOYSA-N 0.000 claims description 5
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 claims description 5
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 claims description 4
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- KLNPWTHGTVSSEU-UHFFFAOYSA-N undecane-1,11-diamine Chemical compound NCCCCCCCCCCCN KLNPWTHGTVSSEU-UHFFFAOYSA-N 0.000 claims description 3
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
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- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Chemical class 0.000 description 1
- 239000002184 metal Chemical class 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 150000002751 molybdenum Chemical class 0.000 description 1
- CWQXQMHSOZUFJS-UHFFFAOYSA-N molybdenum disulfide Chemical compound S=[Mo]=S CWQXQMHSOZUFJS-UHFFFAOYSA-N 0.000 description 1
- 229910052982 molybdenum disulfide Inorganic materials 0.000 description 1
- ACSJOJBMNBXQTG-UHFFFAOYSA-N n-(2-ethylhexyl)benzenesulfonamide Chemical compound CCCCC(CC)CNS(=O)(=O)C1=CC=CC=C1 ACSJOJBMNBXQTG-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 1
- RIKCMEDSBFQFAL-UHFFFAOYSA-N octyl 4-hydroxybenzoate Chemical compound CCCCCCCCOC(=O)C1=CC=C(O)C=C1 RIKCMEDSBFQFAL-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- 229920003192 poly(bis maleimide) Polymers 0.000 description 1
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920006117 poly(hexamethylene terephthalamide)-co- polycaprolactam Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920006396 polyamide 1012 Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920006375 polyphtalamide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- MSVPBWBOFXVAJF-UHFFFAOYSA-N tetradecane-1,14-diamine Chemical compound NCCCCCCCCCCCCCCN MSVPBWBOFXVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Images
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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/265—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from at least two different diamines or at least two different dicarboxylic acids
-
- 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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
- C08J5/04—Reinforcing macromolecular compounds with loose or coherent fibrous material
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
- D01F6/60—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyamides
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Polyamides (AREA)
- General Chemical & Material Sciences (AREA)
- Textile Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
a)1,9−ノナンジアミン、1,10−デカンジアミン、1,11−ウンデカンジアミンおよび1,12−ドデカンジアミンの群から選択されるジアミン、ならびにテレフタル酸からなる組み合わせ50〜95モル%、有利には55〜90モル%、および特に有利には60〜85モル%および
b)2,2,4−トリメチルヘキサメチレンジアミン(2,2,4−TMD)、2,4,4−トリメチルヘキサメチレンジアミン(2,4,4−TMD)およびこれらの混合物の群から選択されるジアミン、ならびにテレフタル酸からなる組み合わせ 5〜50モル%、有利には10〜45モル%、および特に有利には15〜40モル%
から得られるコポリアミドを少なくとも30質量%、有利には少なくとも40質量%、特に有利には少なくとも50質量%、およびとりわけ有利には少なくとも60質量%含有している成形材料によって解決される。
ジアミンおよびジカルボン酸の組み合わせから誘導されるもの。ここでは以下の場合が区別される:
a)ジカルボン酸がテレフタル酸であり、ジアミンは、請求項に記載のジアミンである1,9−ノナンジアミン、1,10−デカンジアミン、1,11−ウンデカンジアミン、1,12−デカンジアミン、2,2,4−TMDおよび2,4,4−TMDとは異なるものである。
a)他のポリマー、
b)繊維状の強化材、
c)充填剤、
d)可塑剤、
e)顔料および/または着色剤、
f)難燃剤、
g)加工助剤、および
h)安定剤。
ポリマーが微粉末として液体中に懸濁している懸濁液と、繊維とを接触させることによる含浸、または
粉末散布法による含浸。
オートクレーブ中に、1,10−デカンジアミン(98.6%のもの)675.2g、2,2,4−TMDおよび2,4,4−TMDからなる混合物150.3g、テレフタル酸789.3g、完全脱塩水(VE水)452g、熱安定剤3.1gおよび5パーセント濃度のH3PO2水溶液2.88gを充填し、窒素で3回不活性化し、オートクレーブを閉じて230℃のオイル循環温度で加熱した。この場合、清澄で均質な塩溶液が形成された。オートクレーブを窒素で44バールの一定した全圧力に調整した。この圧力によって材料は装置を通過した。フラッシャー(位置30)においてポリマー16.5g/hが生じた。分析結果は以下のとおりであった:
カルボキシル末端基含有率:113ミリモル/kg、
アミノ末端基含有率:106ミリモル/kg、
相対溶液粘度ηrel、m−クレゾール中の0.5質量%の溶液、23℃でISO307により測定:1.59、
Tg(ISO11357による):126℃、
Tm1(ISO11357による):256℃(2回目の加熱で測定)、
Tm2(ISO11357による):278℃(主ピーク、2回目の加熱で測定)。
オートクレーブ中に、1,10−デカンジアミン(98.6%のもの)654.9g、2,2,4−TMDおよび2,4,4−TMDからなる混合物38.0g、テレフタル酸664.6g、VE水372.5g、次亜リン酸ナトリウム1.2g、熱安定剤2.4gおよび5パーセント濃度のH3PO2水溶液1.2gを充填し、窒素で3回不活性化し、オートクレーブを閉じて230℃のオイル循環温度で加熱した。この場合、清澄で均質な塩溶液が形成された。オートクレーブを窒素で42バールの一定した全圧力に調整した。この圧力によって材料は装置を通過した。フラッシャーにおいてポリマー17.9g/hが生じた。分析結果は以下のとおりである:
カルボキシル末端基含有率:172ミリモル/kg、
アミノ末端基含有率:167ミリモル/kg、
ηrel:1.42、
Tg:122℃、
Tm:297℃(主ピーク)。
例1に相応して、以下の表に記載の、85:15のデカンジアミン/TMD比を有する更なるコポリアミドを製造した。
例1に相応して、ホモポリマーPA10Tを製造した。
CoPA10T/TMDT(70:30)を製造するために、30lの攪拌式オートクレーブに以下の原料を装入した:
1,10−デカンジアミン(99.3質量%の水溶液として) 3.962kg、
2,2,4−トリメチルヘキサメチレンジアミンおよび2,4,4−トリメチルヘキサメチレンジアミン異性体混合物 1.549kg、
テレフタル酸 5.563kg、ならびに
次亜リン酸の50質量%水溶液(0.006質量%に相応) 1.12gおよび
VE水 5.96kg。
結晶融点Tm:270℃、
相対溶液粘度ηrel:1.76、
COOH末端基:291ミリモル/kg、
NH2末端基:17ミリモル/kg。
CoPA12T/TMDT(60:40)を製造するために、30lの攪拌式オートクレーブに以下の原料を装入した:
1,12−ドデカンジアミン(99.4質量%の水溶液として) 3.788kg、
2,2,4−トリメチルヘキサメチレンジアミンおよび2,4,4−トリメチルヘキサメチレンジアミン異性体混合物 1.982kg、
テレフタル酸 5.305kg、ならびに
次亜リン酸の50質量%水溶液(0.006質量%に相応) 1.13gおよび
VE水 5.96kg。
結晶融点Tm:232℃、
相対溶液粘度ηrel:1.53、
COOH末端基:275ミリモル/kg、
NH2末端基:84ミリモル/kg。
CoPA12T/TMDT(70:30)を製造するために、30lの攪拌式オートクレーブに以下の原料を装入した:
1,12−デカンジアミン(99.4質量%の水溶液として) 4.356kg、
2,2,4−トリメチルヘキサメチレンジアミンおよび2,4,4−トリメチルヘキサメチレンジアミン異性体混合物 1.465kg、
テレフタル酸 5.258kg、ならびに
次亜リン酸の50質量%水溶液(0.006質量%に相応) 1.13gおよび
VE水 5.97kg。
結晶融点Tm:257℃、
相対溶液粘度ηrel:1.56、
COOH末端基:269ミリモル/kg、
NH2末端基:17ミリモル/kg。
例6に相応して、75:25のドデカンジアミン/TMD比を有するコポリアミドを製造した。
例4に相応して、60:40もしくは52:48のデカンジアミン/TMD比を有する2種類のコポリアミドを製造した。
例4に相応して、33:67もしくは12:88のデカンジアミン/TMD比を有するコポリアミドを製造した。
例8からの生成物を、長さ約5mmおよび直径約3mmのストランド成形顆粒として、ピンミル(Alpine CW160)で粉砕した。冷却蛇管により使用顆粒を−50℃に冷却し、粉砕室中で220m/sまで加速し、かつ対向して回転する粉砕ディスクのピンの間で粉砕した。この場合、15kg/hの処理量で粉砕物が生じ、これは100μm未満の粒径を有する割合が50質量%であった。この粉砕物を63μmで篩分けした。得られた微細画分はd10=14.9μm、d50=43.7μm、およびd90=75.4μmの粒径分布(レーザー回折により測定)を有していた。
Claims (8)
- 成形材料であって、以下のモノマー(以下に記載のモル%は、成分a)およびb)の合計に対するものである)
a)1,9−ノナンジアミン、1,10−デカンジアミン、1,11−ウンデカンジアミンおよび1,12−ドデカンジアミンの群から選択されるジアミン、ならびにテレフタル酸からなる組み合わせ50〜95モル%、および
b)2,2,4−トリメチルヘキサメチレンジアミン、2,4,4−トリメチルヘキサメチレンジアミンおよびこれらの混合物の群から選択されるジアミン、ならびにテレフタル酸からなる組み合わせ 5〜50モル%
から得られるコポリアミドを少なくとも30質量%含有しており、前記コポリアミドが、コポリアミド中の全ての成分の合計に対して、別のモノマーから得られる成分を0〜5モル%含有している成形材料。 - 純粋なコポリアミドからなることを特徴とする、請求項1記載の成形材料。
- コポリアミド以外に、少なくとも0.1質量%の添加剤を含有していることを特徴とする、請求項1または2記載の成形材料。
- 粉末であることを特徴とする、請求項1から3までのいずれか1項記載の成形材料。
- 請求項1から4までのいずれか1項記載の成形材料から製造された成形部材。
- 請求項1から4までのいずれか1項記載の成形材料から製造されたシート。
- 請求項1から4までのいずれか1項記載の成形材料から製造されたフィラメント。
- 請求項1から4までのいずれか1項記載の成形材料を含む繊維複合材。
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DE200910027611 DE102009027611A1 (de) | 2009-07-10 | 2009-07-10 | Formmasse auf Basis eines Terephthalsäure- sowie Trimethylhexamethylendiamin-Einheit enthaltenden Copolyamids |
PCT/EP2010/059809 WO2011003973A2 (de) | 2009-07-10 | 2010-07-08 | Formmasse auf basis eines terephthalsäure- sowie trimethylhexamethylendiamin-einheiten enthaltenden copolyamids |
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DE102008002715A1 (de) | 2008-06-27 | 2009-12-31 | Evonik Röhm Gmbh | 2-Hydroxyisobuttersäure produzierende rekombinante Zelle |
DE102010043473A1 (de) | 2010-11-05 | 2012-05-10 | Evonik Degussa Gmbh | Carbon Nanotubes enthaltende Polyamid 12-Zusammensetzung |
DE102010043470A1 (de) | 2010-11-05 | 2012-05-10 | Evonik Degussa Gmbh | Zusammensetzung aus Polyamiden mit niedriger Konzentration an Carbonsäureamidgruppen und elektrisch leitfähigem Kohlenstoff |
CA2842000A1 (en) | 2011-07-20 | 2013-01-24 | Evonik Degussa Gmbh | Oxidation and amination of primary alcohols |
DE102011084518A1 (de) | 2011-10-14 | 2013-04-18 | Evonik Industries Ag | Verwendung einer Mehrschichtfolie mit Polyamid- und Polyesterschichten fürdie Herstellung photovoltaischer Module |
DE102011084521A1 (de) | 2011-10-14 | 2013-04-18 | Evonik Industries Ag | Verwendung einer Mehrschichtfolie mit Polyamid- und Polypropylenschichten für die Herstellung photovoltaischer Module |
EP2639308A1 (de) | 2012-03-12 | 2013-09-18 | Evonik Industries AG | Enzymatische omega-Oxidation und -Aminierung von Fettsäuren |
DE102012204181A1 (de) | 2012-03-16 | 2013-09-19 | Evonik Degussa Gmbh | Elektrisch leitfähigen Kohlenstoff enthaltende Polyamidzusammensetzung |
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WO2011003973A3 (de) | 2011-03-10 |
RU2559328C2 (ru) | 2015-08-10 |
EP2451862B1 (de) | 2018-10-03 |
BR112012000509B1 (pt) | 2019-07-16 |
CN102471482A (zh) | 2012-05-23 |
US8871862B2 (en) | 2014-10-28 |
RU2012104509A (ru) | 2013-08-20 |
US20120095161A1 (en) | 2012-04-19 |
DE102009027611A1 (de) | 2011-01-13 |
KR20120036343A (ko) | 2012-04-17 |
WO2011003973A2 (de) | 2011-01-13 |
CN102471482B (zh) | 2014-01-01 |
JP2012532943A (ja) | 2012-12-20 |
BR112012000509A2 (pt) | 2016-02-16 |
KR101792890B1 (ko) | 2017-11-02 |
EP2451862A2 (de) | 2012-05-16 |
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