JP6272866B2 - 重縮合によるポリアミドの製造方法 - Google Patents
重縮合によるポリアミドの製造方法 Download PDFInfo
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- JP6272866B2 JP6272866B2 JP2015529039A JP2015529039A JP6272866B2 JP 6272866 B2 JP6272866 B2 JP 6272866B2 JP 2015529039 A JP2015529039 A JP 2015529039A JP 2015529039 A JP2015529039 A JP 2015529039A JP 6272866 B2 JP6272866 B2 JP 6272866B2
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- polyamide
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- 239000004952 Polyamide Substances 0.000 title claims description 44
- 229920002647 polyamide Polymers 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 33
- 238000006068 polycondensation reaction Methods 0.000 title claims description 30
- 230000008569 process Effects 0.000 title claims description 28
- 238000002844 melting Methods 0.000 claims description 23
- 230000008018 melting Effects 0.000 claims description 23
- 239000000178 monomer Substances 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 239000007790 solid phase Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 239000012071 phase Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 7
- 230000008859 change Effects 0.000 claims description 6
- 238000009833 condensation Methods 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 230000009477 glass transition Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 241000287463 Phalacrocorax Species 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 8
- -1 alkane dicarboxylic acids Chemical class 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 229920002302 Nylon 6,6 Polymers 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 125000003277 amino group Chemical group 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 239000012778 molding material Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000009757 thermoplastic moulding Methods 0.000 description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 1
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 1
- DQTKCIVHDDGAFK-UHFFFAOYSA-N 2-(5,6-dihydro-4H-cyclopenta[d][1,3]dithiol-2-ylidene)-1,3-dithiole-4,5-dithiol Chemical compound S1C(S)=C(S)SC1=C1SC(CCC2)=C2S1 DQTKCIVHDDGAFK-UHFFFAOYSA-N 0.000 description 1
- FYDMBFIJIQPURU-UHFFFAOYSA-N 2-[2-(2-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=CC=C(N)C=1C(C)(C)C1=CC=CC=C1N FYDMBFIJIQPURU-UHFFFAOYSA-N 0.000 description 1
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 1
- BDBZTOMUANOKRT-UHFFFAOYSA-N 4-[2-(4-aminocyclohexyl)propan-2-yl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1C(C)(C)C1CCC(N)CC1 BDBZTOMUANOKRT-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 229920000577 Nylon 6/66 Polymers 0.000 description 1
- 229920006121 Polyxylylene adipamide Polymers 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- MGIAHHJRDZCTHG-UHFFFAOYSA-N benzene-1,3-dicarboxylic acid;terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1.OC(=O)C1=CC=CC(C(O)=O)=C1 MGIAHHJRDZCTHG-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000000748 compression moulding Methods 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
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000005462 imide group Chemical group 0.000 description 1
- 125000000879 imine group Chemical group 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 229920006024 semi-aromatic copolyamide Polymers 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- KOUDKOMXLMXFKX-UHFFFAOYSA-N sodium oxido(oxo)phosphanium hydrate Chemical compound O.[Na+].[O-][PH+]=O KOUDKOMXLMXFKX-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- BPSKTAWBYDTMAN-UHFFFAOYSA-N tridecane-1,13-diamine Chemical compound NCCCCCCCCCCCCCN BPSKTAWBYDTMAN-UHFFFAOYSA-N 0.000 description 1
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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
- C08G69/04—Preparatory processes
- C08G69/06—Solid state polycondensation
-
- 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
- C08J5/18—Manufacture of films or sheets
-
- 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
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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)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Polyamides (AREA)
Description
PA 26(エチレンジアミン、アジピン酸)
PA 210(エチレンジアミン、セバシン酸)
PA 46(テトラメチレンジアミン、アジピン酸)
PA 66(ヘキサメチレンジアミン、アジピン酸)
PA 69(ヘキサメチレンジアミン、アゼライン酸)
PA 610(ヘキサメチレンジアミン、セバシン酸)
PA 612(ヘキサメチレンジアミン、デカンジカルボン酸)
PA 613(ヘキサメチレンジアミン、ウンデカンジカルボン酸)
PA 1212(1,12−ドデカンジアミン、デカンジカルボン酸)
PA 1313(1,13−ジアミノトリデカン、ウンデカンジカルボン酸)
PA MXD6(m−キシリレンジアミン、アジピン酸)
PA TMDT(トリメチルヘキサメチレンジアミン、テレフタル酸)
ポリフェニレンジアミンテレフタルアミド(p−フェニレンジアミン、テレフタル酸)。
・例えば少なくとも3個のカルボキシル基又はアミノ基を有する、架橋作用のあるモノマー、
・例えばエポキシ基、ヒドロキシ基、イソシアナト基、アミノ基及び/又はカルボキシル基により、カルボキシル基又はアミノ基に結合することができ、かつヒドロキシル基、エーテル基、エステル基、アミド基、イミン基、イミド基、ハロゲン基、シアノ基及びニトロ基、C−C二重結合又はC−C三重結合から選択される官能基を有する、モノマー、
・又はカルボキシル基又はアミノ基に結合することができるポリマーブロック、例えばポリ−p−アラミドオリゴマー
である。
ポリアミド6,6の製造
ポリアミド6,6を、不連続縮合により、二軸スクリューニーダー中で製造した。このために、AH塩1.3kg及び水0.9kgを、混練しながら、段階的に160℃に加熱した。生じた圧力は、その際に約5バールであった。これらの条件下で、大部分の水を留去した。該ニーダーの回転速度は約25分-1であった。約5バールの圧力レベルを、含水量が減少するにつれて、220℃に温度を高めることにより調節し、その際に、その蒸留量を手でニードル弁を用いて調節した。含水量が減少するにつれて、該混合物の蒸気圧が低下し、それにより、該温度は約220℃の最高温度で一定に調節された。
部分芳香族ポリアミドを製造するために、10リットル入る、電気加熱された撹拌タンク反応器を使用した。次の組成のモノマー塩混合物を、室温で導入した:
ヘキサメチレンジアミン 1726.7kg
m−フェニレンビス(メチルアミン) 99.6g
テレフタル酸 1822.3g
イソフタル酸 749.2kg
次亜リン酸ナトリウム一水和物 1.36kg。
Claims (10)
- ポリアミド形成性の、重縮合可能なモノマー及び/又はオリゴマーを、これらを含有し、含水であるが、しかし有機溶剤を含まない反応混合物中で重縮合させることによりポリアミドを製造する方法であって、
該重縮合を、ミキサーを備えた反応器中で、混合しながら、第一工程において液相中で行い、かつ該プロセス中に同じ反応器中で相変化が行われた後に、次の第二工程において固相中で行い、その際に、少なくとも第二工程において、該反応器中の温度が、該ポリアミドの融点を下回り、かつ該重縮合可能なモノマー及び/又はオリゴマーが、該重縮合の最初に、0.5:1〜5:1の範囲内の水に対する質量比で存在する、
ポリアミドを製造する方法。 - 第二工程において、該反応器中の温度が、該ポリアミドのガラス転移温度を上回る、請求項1記載の方法。
- 該ポリアミドが、少なくとも260℃の融点を有する、請求項1又は2記載の方法。
- 第一工程における重縮合の前に、固相中での重縮合は行われない、請求項1から3までのいずれか1項記載の方法。
- 第二工程において、該反応器中の最高温度が、該ポリアミドの融点を少なくとも25℃下回る、請求項1から4までのいずれか1項記載の方法。
- 第二工程において、該反応器中の最高温度が、該ポリアミドの融点を少なくとも30℃下回る、請求項5記載の方法。
- 該重縮合を、最大10バールの圧力で実施する、請求項1から6までのいずれか1項記載の方法。
- 該反応器中の温度が、該重縮合の過程で相変化まで、連続的に及び/又は段階的に上昇する、請求項1から7までのいずれか1項記載の方法。
- 該重縮合中に、第一及び/又は第二工程において水及び/又は該縮合の際に生じる低沸点化合物を、気体で分離する、請求項1から8までのいずれか1項記載の方法。
- 第二工程に続いて、後縮合を周囲圧力で行う、請求項1から9までのいずれか1項記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12182757 | 2012-09-03 | ||
EP12182757.0 | 2012-09-03 | ||
PCT/EP2013/068075 WO2014033294A1 (de) | 2012-09-03 | 2013-09-02 | Verfahren zur herstellung von polyamiden durch polykondensation |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015526578A JP2015526578A (ja) | 2015-09-10 |
JP6272866B2 true JP6272866B2 (ja) | 2018-01-31 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2015529039A Active JP6272866B2 (ja) | 2012-09-03 | 2013-09-02 | 重縮合によるポリアミドの製造方法 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP2892941B1 (ja) |
JP (1) | JP6272866B2 (ja) |
KR (2) | KR20150052862A (ja) |
CN (1) | CN104603178B (ja) |
BR (1) | BR112015004454B1 (ja) |
IL (1) | IL237395A (ja) |
WO (1) | WO2014033294A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
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FR3013356B1 (fr) * | 2013-11-15 | 2018-03-16 | Arkema France | Procede de synthese de polyamide |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1545145A1 (de) * | 1963-04-26 | 1970-01-08 | Glanzstoff Ag | Verfahren zur Herstellung von Polyamiden aus Dicarbonsaeuren und Diaminen bzw. deren Salzen |
JPS5439494A (en) * | 1977-09-05 | 1979-03-26 | Asahi Chem Ind Co Ltd | Continuous preparation of poly-para-phenylene terephthalamide |
JPS5446287A (en) * | 1977-09-21 | 1979-04-12 | Sumitomo Chem Co Ltd | Bulk polycondensation |
US4313870B1 (en) * | 1977-09-21 | 1996-06-18 | Sumitomo Chemical Co | Process for producing polycondensates |
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FR2643377B1 (fr) * | 1989-02-21 | 1992-09-11 | Rhone Poulenc Chimie | Procede de preparation de polyamides semi-aromatiques comprenant des restes d'acide(s) dicarboxylique(s) aromatique(s) et d'alkylpentamethylenediamine |
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SG71170A1 (en) * | 1997-11-18 | 2000-03-21 | Mitsui Chemicals Inc | Process for preparing aromatic polyamides |
DE19923894A1 (de) * | 1999-05-25 | 2000-11-30 | Basf Ag | Verfahren zur Herstellung von Polyamiden |
EP1312633B1 (de) * | 2001-11-15 | 2006-07-26 | EMS Chemie AG | Verfahren zum Herstellen einer Polyamidformmasse |
DE102004059597A1 (de) * | 2004-12-09 | 2006-06-22 | Basf Ag | Blockcopolymere aus Polyethylenterephthalat und dem Polyamid aus meta-Xylylendiamin und Adipinsäure |
BRPI0812711B1 (pt) * | 2007-06-20 | 2018-12-18 | Basf Se | processo para preparar uma poliamida com base em ácidos dicarboxílicos e diaminas |
EP2510044B1 (de) * | 2009-12-08 | 2017-05-31 | Basf Se | Verfahren zur herstellung von polyamiden |
JP5546623B2 (ja) * | 2010-03-26 | 2014-07-09 | ユニチカ株式会社 | 半芳香族ポリアミドの製造方法 |
CN102311545B (zh) * | 2011-10-09 | 2013-02-13 | 卢建国 | 一种生产聚酰胺的方法 |
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KR20150052862A (ko) | 2015-05-14 |
EP2892941B1 (de) | 2016-11-16 |
BR112015004454A8 (pt) | 2019-08-27 |
WO2014033294A1 (de) | 2014-03-06 |
BR112015004454B1 (pt) | 2021-03-23 |
EP2892941A1 (de) | 2015-07-15 |
CN104603178B (zh) | 2017-07-04 |
KR102158813B1 (ko) | 2020-09-23 |
KR20200049903A (ko) | 2020-05-08 |
JP2015526578A (ja) | 2015-09-10 |
IL237395A0 (en) | 2015-04-30 |
IL237395A (en) | 2017-05-29 |
BR112015004454A2 (pt) | 2017-07-04 |
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