JP5174143B2 - ポリアミドの製造方法 - Google Patents
ポリアミドの製造方法 Download PDFInfo
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- JP5174143B2 JP5174143B2 JP2010500247A JP2010500247A JP5174143B2 JP 5174143 B2 JP5174143 B2 JP 5174143B2 JP 2010500247 A JP2010500247 A JP 2010500247A JP 2010500247 A JP2010500247 A JP 2010500247A JP 5174143 B2 JP5174143 B2 JP 5174143B2
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- 239000004952 Polyamide Substances 0.000 title claims description 41
- 229920002647 polyamide Polymers 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title description 11
- 238000006068 polycondensation reaction Methods 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 57
- 239000007791 liquid phase Substances 0.000 claims description 42
- 239000012071 phase Substances 0.000 claims description 38
- 239000000178 monomer Substances 0.000 claims description 36
- 239000007788 liquid Substances 0.000 claims description 25
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical group NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 21
- 230000008569 process Effects 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 20
- 150000004985 diamines Chemical class 0.000 claims description 19
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 18
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical group O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 16
- 239000012530 fluid Substances 0.000 claims description 15
- 150000003951 lactams Chemical group 0.000 claims description 15
- 150000001413 amino acids Chemical class 0.000 claims description 13
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 9
- 239000001361 adipic acid Substances 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 7
- 229920002292 Nylon 6 Polymers 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 239000007790 solid phase Substances 0.000 claims description 6
- 238000010924 continuous production Methods 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- YTAHJIFKAKIKAV-XNMGPUDCSA-N [(1R)-3-morpholin-4-yl-1-phenylpropyl] N-[(3S)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]carbamate Chemical compound O=C1[C@H](N=C(C2=C(N1)C=CC=C2)C1=CC=CC=C1)NC(O[C@H](CCN1CCOCC1)C1=CC=CC=C1)=O YTAHJIFKAKIKAV-XNMGPUDCSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
- 239000012266 salt solution Substances 0.000 description 3
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 2
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000007730 finishing process Methods 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
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- -1 poly (hexamethylene) Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- ACPFWKHFWRDQEI-UHFFFAOYSA-N 2,2,7,7-tetramethyloctane-1,8-diamine Chemical compound NCC(C)(C)CCCCC(C)(C)CN ACPFWKHFWRDQEI-UHFFFAOYSA-N 0.000 description 1
- TUGAQVRNALIPHY-UHFFFAOYSA-N 2,2-dimethylpentane-1,5-diamine Chemical compound NCC(C)(C)CCCN TUGAQVRNALIPHY-UHFFFAOYSA-N 0.000 description 1
- DPQHRXRAZHNGRU-UHFFFAOYSA-N 2,4,4-trimethylhexane-1,6-diamine Chemical compound NCC(C)CC(C)(C)CCN DPQHRXRAZHNGRU-UHFFFAOYSA-N 0.000 description 1
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 1
- PFKKTUJMQOKZOR-UHFFFAOYSA-N 2-[3-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1CCCC(CC(O)=O)C1 PFKKTUJMQOKZOR-UHFFFAOYSA-N 0.000 description 1
- GDYYIJNDPMFMTB-UHFFFAOYSA-N 2-[3-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC(CC(O)=O)=C1 GDYYIJNDPMFMTB-UHFFFAOYSA-N 0.000 description 1
- HASUJDLTAYUWCO-UHFFFAOYSA-N 2-aminoundecanoic acid Chemical compound CCCCCCCCCC(N)C(O)=O HASUJDLTAYUWCO-UHFFFAOYSA-N 0.000 description 1
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 description 1
- BUGIFNPYQVKODR-UHFFFAOYSA-N 2-methylhexane-1,6-diamine Chemical compound NCC(C)CCCCN BUGIFNPYQVKODR-UHFFFAOYSA-N 0.000 description 1
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- LTZQJVGOFCCDQA-UHFFFAOYSA-N 3-methylhexane-1,6-diamine Chemical compound NCCC(C)CCCN LTZQJVGOFCCDQA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LKJKDWUEGGOHFB-UHFFFAOYSA-N 4-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1C(O)=O LKJKDWUEGGOHFB-UHFFFAOYSA-N 0.000 description 1
- DZCPFKFMCCYUOU-UHFFFAOYSA-N 5-methylnonane-1,1-diamine Chemical compound CCCCC(C)CCCC(N)N DZCPFKFMCCYUOU-UHFFFAOYSA-N 0.000 description 1
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
- XDOLZJYETYVRKV-UHFFFAOYSA-N 7-Aminoheptanoic acid Chemical compound NCCCCCCC(O)=O XDOLZJYETYVRKV-UHFFFAOYSA-N 0.000 description 1
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-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
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940059260 amidate Drugs 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001276 controlling effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- KEIQPMUPONZJJH-UHFFFAOYSA-N dicyclohexylmethanediamine Chemical compound C1CCCCC1C(N)(N)C1CCCCC1 KEIQPMUPONZJJH-UHFFFAOYSA-N 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
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- ZDGGJQMSELMHLK-UHFFFAOYSA-N m-Trifluoromethylhippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(C(F)(F)F)=C1 ZDGGJQMSELMHLK-UHFFFAOYSA-N 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012768 molten material Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical compound OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- DDLUSQPEQUJVOY-UHFFFAOYSA-N nonane-1,1-diamine Chemical compound CCCCCCCCC(N)N DDLUSQPEQUJVOY-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920005586 poly(adipic acid) Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920006345 thermoplastic polyamide Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000012808 vapor phase Substances 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
- 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
-
- 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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic 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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
-
- 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
- C08G69/08—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids
- C08G69/14—Lactams
- C08G69/16—Preparatory processes
- C08G69/18—Anionic polymerisation
-
- 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
- C08G69/28—Preparatory processes
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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)
- Polyamides (AREA)
Description
・工程1:モノマーを含む液体流を反応器中で大気圧より高い圧力P1において重縮合させる。反応器出口における材料の流れは少なくとも水蒸気を含む気相と少なくとも重縮合生成物を含む液相とから成る。
・工程2:材料の流れをチャンバーに供給し、気相の少なくとも一部をチャンバーから排気し、少なくとも(重縮合生成物を少なくとも含む)液相を回収する。チャンバー内の圧力P2は、大気圧より高い設定値であってチャンバー内における液相の滞留時間が5分未満、好ましくは1分未満になるような前記設定値に調節する。
・工程3:工程2の際に回収された重縮合生成物の流れを少なくとも含む液相の圧力低下をもたらす。
進行度(%)=[(生成したアミド単位のモル数)/(不足していた初期反応性官能基のモル数)]×100
・反応媒体中に最初に不足していた反応性官能基が(アミン官能基に対する)カルボン酸官能基である場合には、この反応媒体中に最初に存在していたモノマーから得られたカルボン酸官能基のモル数であり、
・反応媒体中に最初に不足していた反応性官能基が(カルボン酸官能基に対する)アミン官能基である場合には、この反応媒体中に最初に存在していたモノマーから得られたアミン官能基のモル数である。
Claims (28)
- 少なくとも次の工程:
・工程1:モノマーを含む液体流を反応器中で大気圧より高い圧力P1において重縮合させる;反応器出口における材料の流れは少なくとも水蒸気を含む気相と少なくとも重縮合生成物を含む液相とから成る;
・工程2:材料の流れをチャンバーに供給し、気相の少なくとも一部をチャンバーから排気し、少なくとも重縮合生成物を少なくとも含む液相を回収する;チャンバー内の圧力P2は、0.5〜2.5MPaの範囲の設定値に調節する;
・工程3:工程2の際に回収された重縮合生成物の流れを少なくとも含む液相の圧力低下をもたらす:
を含む、ポリアミドの連続式製造方法。 - 工程1において、前記液体流を大気圧より高い圧力P'1において供給し、反応器の出口における材料の流れが前記供給圧力P'1より低く大気圧より高い圧力P''1にあることを特徴とする、請求項1に記載の方法。
- 工程2において、チャンバー内の圧力P2を、チャンバー内に液相が残らないような設定値に調節することを特徴とする、請求項1又は2に記載の方法。
- 前記反応器が管状反応器であることを特徴とする、請求項1〜3のいずれかに記載の方法。
- 前記モノマーがジカルボン酸及びジアミンであることを特徴とする、請求項1〜4のいずれかに記載の方法。
- 前記ポリアミドがポリアミド66又は繰返し単位の大半がポリアミド66単位であるコポリアミドであり、前記ジカルボン酸がアジピン酸であり且つ前記ジアミンがヘキサメチレンジアミンであることを特徴とする、請求項5に記載の方法。
- 前記モノマーがラクタム及び/又はアミノ酸であることを特徴とする、請求項1〜4のいずれかに記載の方法。
- 前記ポリアミドがポリアミド6又は繰返し単位の大半がポリアミド6単位であるコポリアミドであり、前記ラクタムがカプロラクタムであり、そして/又は前記アミノ酸がアミノヘキサン酸であることを特徴とする、請求項7に記載の方法。
- 前記モノマーを含む液体流が水溶液であることを特徴とする、請求項1〜8のいずれかに記載の方法。
- 前記液体流がモノマーを50〜100重量%含むことを特徴とする、請求項1〜9のいずれかに記載の方法。
- 前記管状反応器への供給流が1MPa超の圧力P'1にあることを特徴とする、請求項4〜10のいずれかに記載の方法。
- 前記管状反応器の出口における材料の流れが0.5MPa超の圧力P''1及び200℃超の温度にあることを特徴とする、請求項4〜11のいずれかに記載の方法。
- 前記反応器の出口における重縮合の進行度がポリアミド66について90%超であることを特徴とする、請求項6及び9〜12のいずれかに記載の方法。
- 前記反応器中の液相の滞留時間が5分超であることを特徴とする、請求項1〜13のいずれかに記載の方法。
- 前記管状反応器が直径が異なる部分を1以上含み、その長さ/直径比が100より大きいことを特徴とする、請求項4〜14のいずれかに記載の方法。
- 前記管状反応器が反応器の入口から出口に向けて直径が大きくなる複数の箇所を含むことを特徴とする、請求項4〜15のいずれかに記載の方法。
- 前記反応器の液相の表面速度が0.1m/秒超であることを特徴とする、請求項1〜16のいずれかに記載の方法。
- 前記反応器が熱交換流体を含むチャンバー又はジャケット内に入れられることを特徴とする、請求項1〜17のいずれかに記載の方法。
- 排気される気相のスループットを、排気を行うチャンバー内(より特定的にはチャンバー内の液相を回収するための箇所)における液相のレベルの検知に従って制御し、設定レベルを超えたら気相の排気のためのスループットを減らすことを特徴とする、請求項1〜18のいずれかに記載の方法。
- 材料の流れが供給される円筒状部分と、重縮合生成物の液相を回収するための円錐状部分と、気相を排気するための装置とを含むサイクロンタイプの装置中で排気を実施することを特徴とする、請求項1〜19のいずれかに記載の方法。
- 少なくとも重縮合生成物の流れを含む液相の圧力低下を、断面積が大きくなる複数の箇所を含むことができる管状装置中で実施することを特徴とする、請求項1〜20のいずれかに記載の方法。
- 前記の管状の圧力低下用装置が熱交換流体を含むチャンバー又はジャケット中に入れられることを特徴とする、請求項21に記載の方法。
- 蒸気の形の熱流体の発生器をチャンバー中に存在させることを特徴とする、請求項22に記載の方法。
- 工程3から得られる生成物の流れの重縮合の進行度がポリアミド66について90%超であることを特徴とする、請求項1〜23のいずれかに記載の方法。
- 工程3の後に溶融相中での重縮合仕上げ工程又は固相中での後縮合を実施することを特徴とする、請求項1〜24のいずれかに記載の方法。
- 前記の仕上げ工程又は固相中での後縮合工程の前に、圧力低下工程から出て来た流れ中に存在する気相を分離する工程を実施することを特徴とする、請求項25に記載の方法。
- 前記仕上げ用の装置を熱交換流体を用いて加熱することを特徴とする、請求項25又は26に記載の方法。
- 工程2と工程3との間に、工程2から得られた液相から出発して、それぞれ工程1及び工程2に類似した重縮合i及び排気jの連続工程を少なくとも1組含み、工程iの重縮合の管状反応器中の圧力及び工程jの排気チャンバー中の圧力が大気圧より高く、工程iの重縮合の管状反応器中の入口圧力P'iが工程iの出口圧力P''iより高いことを特徴とする、請求項1〜27のいずれかに記載の方法。
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FR0702199A FR2914308B1 (fr) | 2007-03-27 | 2007-03-27 | Procede de fabrication de polyamide |
PCT/EP2008/053491 WO2008125429A1 (fr) | 2007-03-27 | 2008-03-25 | Procede de fabrication de polyamide |
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ES2632205T3 (es) * | 2008-12-12 | 2017-09-11 | Basf Se | Procedimiento para la fabricación continua de copoliamidas a partir de lactamas y de sales diaminas y ácidos dicarboxílicos |
FR2953755B1 (fr) * | 2009-12-14 | 2012-01-20 | Rhodia Operations | Procede de fabrication d'articles composite a base de polyamide |
FR2981600B1 (fr) | 2011-10-25 | 2013-11-15 | Rhodia Operations | Procede de preparation de granules de polyamide |
TW201501794A (zh) * | 2013-05-01 | 2015-01-16 | Invista Tech Sarl | 用於清潔或維護攪動式高壓釜排氣系統之系統及方法 |
MY173327A (en) * | 2013-06-12 | 2020-01-15 | Basf Se | Device for the synthesis of a polymer extraction of a gaseous substance comprising a reaction chamber having at lease one circular-cylindrical section |
FR3029923B1 (fr) * | 2014-12-12 | 2018-04-27 | Arkema France | Procede de preparation d'un polyamide semi-aromatique |
TWI794146B (zh) * | 2015-12-01 | 2023-03-01 | 美商阿散德性能材料營運公司 | 具有均一相對黏度及低凝膠含量之高分子量聚醯胺及共聚醯胺 |
MX2019014732A (es) | 2017-06-08 | 2020-08-03 | Ascend Performance Mat Operations Llc | Nanofibras de poliamida no tejidas. |
US11376534B2 (en) | 2017-06-08 | 2022-07-05 | Ascend Performance Materials Operations Llc | Polyamide nanofiber nonwovens for filters |
JP7395512B2 (ja) | 2018-06-08 | 2023-12-11 | アセンド・パフォーマンス・マテリアルズ・オペレーションズ・リミテッド・ライアビリティ・カンパニー | 調節可能なナノファイバー不織布製品 |
EP3814400A1 (en) | 2018-06-27 | 2021-05-05 | Ascend Performance Materials Operations LLC | Processes for removing residual caprolactam via ssp water addition |
TWI729633B (zh) | 2018-12-18 | 2021-06-01 | 美商阿散德性能材料營運公司 | 具有鋅含量的抗微生物非織造聚醯胺 |
WO2020146308A1 (en) | 2019-01-07 | 2020-07-16 | Ascend Performance Materials Operations Llc | Non-halogenated flame retardant polyamide compositions |
CA3128002A1 (en) | 2019-01-31 | 2020-08-06 | Ascend Performance Materials Operations Llc | Impact-modified injection-molded polyamide |
KR20210126672A (ko) | 2019-02-12 | 2021-10-20 | 어센드 퍼포먼스 머티리얼즈 오퍼레이션즈 엘엘씨 | 내가수분해성 폴리아미드 |
CN113661214A (zh) | 2019-04-01 | 2021-11-16 | 奥升德功能材料运营有限公司 | 非卤化阻燃性聚酰胺组合物 |
BR112021020488A2 (pt) | 2019-05-01 | 2022-02-15 | Ascend Performance Mat Operations Llc | Meio filtrante compreendendo camada de nanofibra de poliamida |
WO2021127306A1 (en) | 2019-12-18 | 2021-06-24 | Ascend Performance Materials Operations Llc | Processes for producing fiber and fabrics with zinc content |
MX2023001795A (es) | 2020-08-13 | 2023-03-10 | Ascend Performance Mat Operations Llc | Poliamidas alifaticas y semi-aromaticas con acidos dimeros y aminas dimeras. |
CA3196476A1 (en) | 2020-10-30 | 2022-05-05 | Albert Ortega | Polyamide nonwovens in sound absorbing multi-layer composites |
WO2023058903A1 (ko) * | 2021-10-08 | 2023-04-13 | 포항공과대학교 산학협력단 | 자동화된 마이크로 조합화학 반응장치 및 그를 이용한 최적화 조합화학 합성방법 |
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US3948862A (en) * | 1974-05-06 | 1976-04-06 | E. I. Du Pont De Nemours And Company | Continuous process for preparing aliphatic polycarbonamides |
SU620494A1 (ru) * | 1974-08-12 | 1978-08-25 | Предприятие П/Я М-5885 | Непрерывный способ получени полиамидов |
DE3321579A1 (de) * | 1983-06-15 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von polyamiden |
DE3321581A1 (de) * | 1983-06-15 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von polyamiden |
DE4321683A1 (de) * | 1993-06-30 | 1995-01-12 | Basf Ag | Verfahren zum kontinuierlichen Herstellen von niedermolekularen Polyamiden |
ES2210798T3 (es) * | 1997-08-28 | 2004-07-01 | E.I. Du Pont De Nemours And Company | Proceso de preparacion de poliamidas. |
DE19804023A1 (de) * | 1998-02-02 | 1999-08-05 | Basf Ag | Kontinuierliches Verfahren zur Herstellung von Polyamiden aus Aminonitrilen |
JP2000159885A (ja) * | 1998-12-02 | 2000-06-13 | Ube Ind Ltd | ポリアミド樹脂組成物の製造方法 |
DE19957663A1 (de) * | 1999-11-30 | 2001-05-31 | Basf Ag | Verfahren zur kontinuierlichen Herstellung von Copolyamiden, die auf einem Lactam (I), einem Diamin (II) und einer Dicarbonsäure (III) basieren |
FR2814747B1 (fr) * | 2000-10-04 | 2002-12-06 | Rhodianyl | Procede de fabrication de polyamides |
JP4151354B2 (ja) * | 2002-08-30 | 2008-09-17 | 東洋紡績株式会社 | ポリアミドの連続製造方法 |
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FR2914308B1 (fr) | 2009-05-01 |
ATE523545T1 (de) | 2011-09-15 |
JP2010522786A (ja) | 2010-07-08 |
TW200902591A (en) | 2009-01-16 |
KR101141569B1 (ko) | 2012-05-21 |
IL201000A0 (en) | 2010-05-17 |
BRPI0808584B1 (pt) | 2018-07-03 |
CA2681357A1 (fr) | 2008-10-23 |
PL2129702T3 (pl) | 2012-01-31 |
RU2451036C2 (ru) | 2012-05-20 |
CA2681357C (fr) | 2012-05-29 |
IL201000A (en) | 2013-05-30 |
EP2129702B1 (fr) | 2011-09-07 |
ES2373182T3 (es) | 2012-02-01 |
MX2009010319A (es) | 2009-11-25 |
CN101675093A (zh) | 2010-03-17 |
AR067281A1 (es) | 2009-10-07 |
RU2009139649A (ru) | 2011-05-10 |
KR20090125147A (ko) | 2009-12-03 |
US20100144986A1 (en) | 2010-06-10 |
US8759475B2 (en) | 2014-06-24 |
FR2914308A1 (fr) | 2008-10-03 |
EP2129702A1 (fr) | 2009-12-09 |
BRPI0808584A2 (pt) | 2014-08-12 |
CN101675093B (zh) | 2011-12-28 |
WO2008125429A1 (fr) | 2008-10-23 |
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