JP5599726B2 - ポリアミドの製造 - Google Patents
ポリアミドの製造 Download PDFInfo
- Publication number
- JP5599726B2 JP5599726B2 JP2010545483A JP2010545483A JP5599726B2 JP 5599726 B2 JP5599726 B2 JP 5599726B2 JP 2010545483 A JP2010545483 A JP 2010545483A JP 2010545483 A JP2010545483 A JP 2010545483A JP 5599726 B2 JP5599726 B2 JP 5599726B2
- Authority
- JP
- Japan
- Prior art keywords
- cation
- group
- ionic liquid
- acid
- polyamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 229920002647 polyamide Polymers 0.000 title claims description 60
- 239000004952 Polyamide Substances 0.000 title claims description 59
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 239000002608 ionic liquid Substances 0.000 claims description 66
- -1 pyridazinium ion Chemical class 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 35
- 150000001768 cations Chemical class 0.000 claims description 31
- 239000000178 monomer Substances 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 28
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 25
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 25
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 22
- 150000004985 diamines Chemical class 0.000 claims description 19
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000010408 film Substances 0.000 claims description 17
- 229920000642 polymer Polymers 0.000 claims description 17
- 150000001450 anions Chemical class 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 15
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- 238000000576 coating method Methods 0.000 claims description 12
- 239000000835 fiber Substances 0.000 claims description 12
- 235000011037 adipic acid Nutrition 0.000 claims description 11
- 239000001361 adipic acid Substances 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 11
- 239000010409 thin film Substances 0.000 claims description 11
- 229920002292 Nylon 6 Polymers 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 9
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 150000003951 lactams Chemical class 0.000 claims description 8
- 235000021317 phosphate Nutrition 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 7
- 239000004760 aramid Substances 0.000 claims description 7
- 229920003235 aromatic polyamide Polymers 0.000 claims description 7
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000005219 aminonitrile group Chemical group 0.000 claims description 6
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 6
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 6
- 238000012546 transfer Methods 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 4
- HCUZVMHXDRSBKX-UHFFFAOYSA-N 2-decylpropanedioic acid Chemical compound CCCCCCCCCCC(C(O)=O)C(O)=O HCUZVMHXDRSBKX-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 4
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 4
- 229920003189 Nylon 4,6 Polymers 0.000 claims description 3
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 3
- 238000007306 functionalization reaction Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical group OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 2
- ZXIIJFIFQBKWJN-UHFFFAOYSA-N 2,3-dimethyl-1h-imidazol-3-ium;dimethyl phosphate Chemical compound COP([O-])(=O)OC.C[NH+]1C=CN=C1C ZXIIJFIFQBKWJN-UHFFFAOYSA-N 0.000 claims description 2
- GIWQSPITLQVMSG-UHFFFAOYSA-O 2,3-dimethylimidazolium ion Chemical compound CC1=[NH+]C=CN1C GIWQSPITLQVMSG-UHFFFAOYSA-O 0.000 claims description 2
- FWPKWVUFQDXPBW-UHFFFAOYSA-N 9-amino-decanoic acid Chemical compound CC(N)CCCCCCCC(O)=O FWPKWVUFQDXPBW-UHFFFAOYSA-N 0.000 claims description 2
- 101000836394 Homo sapiens Sestrin-1 Proteins 0.000 claims description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 2
- 229920006121 Polyxylylene adipamide Polymers 0.000 claims description 2
- 102100027288 Sestrin-1 Human genes 0.000 claims description 2
- SNPIMBDCLUUDST-UHFFFAOYSA-N aziridin-2-one Chemical compound O=C1CN1 SNPIMBDCLUUDST-UHFFFAOYSA-N 0.000 claims description 2
- MZOZUBDVCUSFCU-UHFFFAOYSA-N benzene-1,4-diamine;benzene-1,4-dicarboxamide Chemical compound NC1=CC=C(N)C=C1.NC(=O)C1=CC=C(C(N)=O)C=C1 MZOZUBDVCUSFCU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- PMCPUPRECKXGEW-UHFFFAOYSA-N diethyl phosphate;2-ethyl-1-methyl-1h-imidazol-1-ium Chemical compound CCC1=NC=C[NH+]1C.CCOP([O-])(=O)OCC PMCPUPRECKXGEW-UHFFFAOYSA-N 0.000 claims description 2
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005462 imide group Chemical group 0.000 claims description 2
- 125000000879 imine group Chemical group 0.000 claims description 2
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
- ZETYUTMSJWMKNQ-UHFFFAOYSA-N n,n',n'-trimethylhexane-1,6-diamine Chemical compound CNCCCCCCN(C)C ZETYUTMSJWMKNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- BPSKTAWBYDTMAN-UHFFFAOYSA-N tridecane-1,13-diamine Chemical compound NCCCCCCCCCCCCCN BPSKTAWBYDTMAN-UHFFFAOYSA-N 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-P pyrimidine-1,3-diium Chemical compound C1=C[NH+]=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-P 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000005345 coagulation Methods 0.000 description 8
- 230000015271 coagulation Effects 0.000 description 8
- 238000007056 transamidation reaction Methods 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000006068 polycondensation reaction Methods 0.000 description 5
- 239000003586 protic polar solvent Substances 0.000 description 5
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000009790 rate-determining step (RDS) Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 2
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical class CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 229920000577 Nylon 6/66 Polymers 0.000 description 2
- 229920002614 Polyether block amide Polymers 0.000 description 2
- 238000006887 Ullmann reaction Methods 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 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
- 238000002156 mixing Methods 0.000 description 2
- 150000002892 organic cations Chemical class 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229920006024 semi-aromatic copolyamide Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-M 1,1-dioxo-1,2-benzothiazol-3-olate Chemical compound C1=CC=C2C([O-])=NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-M 0.000 description 1
- PWNQRCRMEYGPNQ-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-d][1,4]diazepine Chemical compound C1CNCCN2CCCC=C21 PWNQRCRMEYGPNQ-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical class [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-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
- UINDRJHZBAGQFD-UHFFFAOYSA-O 2-ethyl-3-methyl-1h-imidazol-3-ium Chemical compound CCC1=[NH+]C=CN1C UINDRJHZBAGQFD-UHFFFAOYSA-O 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- 229910017008 AsF 6 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 101000576320 Homo sapiens Max-binding protein MNT Proteins 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical group NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 1
- 229920000393 Nylon 6/6T Polymers 0.000 description 1
- 229920000007 Nylon MXD6 Polymers 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-O Piperidinium(1+) Chemical compound C1CC[NH2+]CC1 NQRYJNQNLNOLGT-UHFFFAOYSA-O 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000005700 Putrescine Substances 0.000 description 1
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-O Pyrazolium Chemical compound C1=CN[NH+]=C1 WTKZEGDFNFYCGP-UHFFFAOYSA-O 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 1
- 229910018286 SbF 6 Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 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
- XQIMLPCOVYNASM-UHFFFAOYSA-N borole Chemical class B1C=CC=C1 XQIMLPCOVYNASM-UHFFFAOYSA-N 0.000 description 1
- 125000000707 boryl group Chemical group B* 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 229920006177 crystalline aliphatic polyamide Polymers 0.000 description 1
- 229920006038 crystalline resin Polymers 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical class C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 1
- MARBGPJPPMSWGK-UHFFFAOYSA-N diethyl hydrogen phosphate;5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1.CCOP(O)(=O)OCC MARBGPJPPMSWGK-UHFFFAOYSA-N 0.000 description 1
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000002240 furans Chemical class 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-O hydron;1,3-oxazole Chemical compound C1=COC=[NH+]1 ZCQWOFVYLHDMMC-UHFFFAOYSA-O 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 150000004693 imidazolium salts Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 150000002476 indolines Chemical class 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003854 isothiazoles Chemical class 0.000 description 1
- 150000002545 isoxazoles Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- IYGMJRCUQOOENU-UHFFFAOYSA-N oxaphosphole Chemical class C1=COP=C1 IYGMJRCUQOOENU-UHFFFAOYSA-N 0.000 description 1
- PUPAWTXNPAJCHR-UHFFFAOYSA-N oxazaborole Chemical class O1C=CB=N1 PUPAWTXNPAJCHR-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 150000003853 pentazoles Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 229920006112 polar polymer Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000007017 scission Effects 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
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009777 vacuum freeze-drying Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002759 woven fabric 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0287—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing atoms other than nitrogen as cationic centre
- B01J31/0288—Phosphorus
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0287—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing atoms other than nitrogen as cationic centre
- B01J31/0289—Sulfur
-
- 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
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyamides (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08151256 | 2008-02-11 | ||
| EP08151256.8 | 2008-02-11 | ||
| PCT/EP2009/051385 WO2009101032A1 (de) | 2008-02-11 | 2009-02-06 | Verfahren zur herstellung von polyamiden |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011525935A JP2011525935A (ja) | 2011-09-29 |
| JP2011525935A5 JP2011525935A5 (OSRAM) | 2012-03-22 |
| JP5599726B2 true JP5599726B2 (ja) | 2014-10-01 |
Family
ID=40445320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010545483A Expired - Fee Related JP5599726B2 (ja) | 2008-02-11 | 2009-02-06 | ポリアミドの製造 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8618225B2 (OSRAM) |
| EP (1) | EP2252397A1 (OSRAM) |
| JP (1) | JP5599726B2 (OSRAM) |
| KR (1) | KR20100126678A (OSRAM) |
| CN (1) | CN101970108B (OSRAM) |
| BR (1) | BRPI0908350A2 (OSRAM) |
| CA (1) | CA2713781A1 (OSRAM) |
| MX (1) | MX2010008671A (OSRAM) |
| WO (1) | WO2009101032A1 (OSRAM) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5661616B2 (ja) * | 2008-06-20 | 2015-01-28 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | ポリアミドペレットの多段階乾燥及び後縮合を連続的に行う方法 |
| KR101699558B1 (ko) * | 2008-08-14 | 2017-02-13 | 바스프 에스이 | 폴리아미드를 제조하기 위한 회분식 방법 |
| US8772438B2 (en) | 2009-07-09 | 2014-07-08 | Invista North America S.är.l. | Preparation of polyamides |
| ES2639062T3 (es) | 2009-12-08 | 2017-10-25 | Basf Se | Proceso para la preparación de poliamidas |
| WO2011094673A2 (en) * | 2010-02-01 | 2011-08-04 | Invista Technologies S.A R.L. | Bio-based terpolymers and process of making the same |
| EP2468811A1 (de) | 2010-12-21 | 2012-06-27 | Basf Se | Thermoplastische Formmasse |
| EP2468812A1 (de) | 2010-12-21 | 2012-06-27 | Basf Se | Thermoplastische Formmasse |
| US8580886B2 (en) | 2011-09-20 | 2013-11-12 | Dow Corning Corporation | Method for the preparation and use of bis (alkoxysilylorgano)-dicarboxylates |
| EP2785726B1 (en) | 2011-12-02 | 2018-08-01 | Dow Silicones Corporation | Ester-functional silanes and the preparation and use thereof; and use of iminium compounds as phase transfer catalysts |
| EP2981641B1 (en) * | 2013-04-04 | 2024-05-15 | Aalto University Foundation sr | Process for the production of shaped cellulose articles |
| KR102070137B1 (ko) * | 2013-12-30 | 2020-01-28 | 코오롱인더스트리 주식회사 | 공중합 아라미드 원착사 및 그의 제조방법 |
| CN106232895B (zh) | 2014-04-16 | 2018-11-09 | 普罗奥尼克股份有限公司 | 用于熔融芳族聚酰胺/芳族聚酰胺纤维的方法 |
| JPWO2015186364A1 (ja) * | 2014-06-06 | 2017-04-20 | 株式会社ブリヂストン | タイヤ |
| GB201419605D0 (en) * | 2014-11-04 | 2014-12-17 | Univ Leuven Kath | Improved method for synthesis of polyamide composite membranes |
| EP3034577A1 (en) | 2014-12-19 | 2016-06-22 | The Goodyear Tire & Rubber Company | Tire with thermoplastic innerliner |
| DE102015117682A1 (de) * | 2015-10-16 | 2017-04-20 | Fuchshuber Techno-Tex Gmbh | Koagulierbare Polymerlösung mit darin gelösten aromatischen Hochleistungspolymeren, ein Verfahren zu deren Gewinnung und deren Verwendung |
| FR3054236B1 (fr) * | 2016-07-25 | 2018-07-13 | Arkema France | Procede de synthese de polyamide pa 6-6 |
| WO2018050489A1 (de) * | 2016-09-14 | 2018-03-22 | Basf Se | Verfahren zur herstellung eines polybenzazolpolymers (p) |
| CN111206305B (zh) * | 2020-02-26 | 2021-11-05 | 江苏奥神新材料股份有限公司 | 一种用于聚酰亚胺初生丝废丝环化的装备及环化方法 |
| CN114213845A (zh) * | 2021-12-10 | 2022-03-22 | 中化学科学技术研究有限公司 | 一种可纺聚酰胺及其制备方法和制品 |
| CN115181305B (zh) * | 2022-07-25 | 2023-11-03 | 河北金力新能源科技股份有限公司 | 改性聚酰亚胺质子交换膜及其制备方法 |
| CN115558142A (zh) * | 2022-10-20 | 2023-01-03 | 苏州润佳高分子材料有限公司 | 一种增塑尼龙6材料的制备方法 |
| CN119505228A (zh) * | 2024-11-22 | 2025-02-25 | 中国科学院过程工程研究所 | 一种离子液体接枝改性耐高温生物基尼龙及其制备方法和应用 |
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| US2071250A (en) | 1931-07-03 | 1937-02-16 | Du Pont | Linear condensation polymers |
| US2071251A (en) | 1931-07-03 | 1937-02-16 | Du Pont | Fiber and method of producing it |
| US2130523A (en) | 1935-01-02 | 1938-09-20 | Du Pont | Linear polyamides and their production |
| US2130948A (en) | 1937-04-09 | 1938-09-20 | Du Pont | Synthetic fiber |
| US2241322A (en) | 1938-09-30 | 1941-05-06 | Du Pont | Process for preparing polyamides from cyclic amides |
| US2312966A (en) | 1940-04-01 | 1943-03-02 | Du Pont | Polymeric material |
| US2512606A (en) | 1945-09-12 | 1950-06-27 | Du Pont | Polyamides and method for obtaining same |
| IL24111A (en) | 1964-08-24 | 1969-02-27 | Du Pont | Linear polyamides |
| NL8001764A (nl) | 1980-03-26 | 1981-10-16 | Stamicarbon | Bereiding van hoogmoleculair polytramethyleenadipamide. |
| NL8001763A (nl) | 1980-03-26 | 1981-10-16 | Stamicarbon | Bereiding van polytetramethyleenadipamide. |
| NL8001762A (nl) | 1980-03-26 | 1981-10-16 | Stamicarbon | Bereiding van voorwerpen op de basis van polyamide. |
| DE3321581A1 (de) | 1983-06-15 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von polyamiden |
| DE3321579A1 (de) | 1983-06-15 | 1984-12-20 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von polyamiden |
| DE3723688A1 (de) | 1987-07-17 | 1989-01-26 | Basf Ag | Teilaromatische copolyamide mit verringertem triamingehalt |
| US5298595A (en) | 1987-07-17 | 1994-03-29 | Basf Aktiengesellschaft | Partly aromatic copolyamides of reduced triamine content |
| DE3889787D1 (de) | 1987-07-17 | 1994-07-07 | Basf Ag | Teilaromatische Copolyamide mit verringertem Triamingehalt. |
| US5218082A (en) | 1987-07-17 | 1993-06-08 | Basf Aktiengesellschaft | Partly aromatic copolyamide of reduced triamine content |
| US5252661A (en) | 1987-07-17 | 1993-10-12 | Basf Aktiengesellschaft | Impact modifying rubber and partly aromatic copolyamides |
| DE4413177A1 (de) | 1994-04-15 | 1995-10-19 | Basf Ag | Inhärent hitzestabilisierte Polyamide |
| UA41404C2 (uk) | 1994-04-15 | 2001-09-17 | Басф Акцієнгезельшафт | Спосіб одержання поліаміду, інгерентно світло- та термостабілізований поліамід, нитки та полотно, одержане з ниток |
| CA2440528C (en) | 2001-03-20 | 2010-02-02 | Basf Aktiengesellschaft | Ionic liquids as selective additives for the separation of close-boiling or azeotropic mixtures |
| US6924341B2 (en) | 2001-03-30 | 2005-08-02 | The Uab Research Foundation | Polymer formation in room temperature ionic liquids |
| US6808557B2 (en) | 2001-10-03 | 2004-10-26 | The University Of Alabama | Cellulose matrix encapsulation and method |
| US6824599B2 (en) | 2001-10-03 | 2004-11-30 | The University Of Alabama | Dissolution and processing of cellulose using ionic liquids |
| MY138064A (en) | 2002-01-24 | 2009-04-30 | Basf Ag | Method for the separation of acids from chemical reaction mixtures by means of ionic fluids |
| DE10202838A1 (de) | 2002-01-24 | 2003-08-07 | Basf Ag | Verfahren zur Abtrennung von Säuren aus chemischen Reaktionsgemischen mit Hilfe von ionischen Flüssigkeiten |
| DE10243181A1 (de) * | 2002-07-05 | 2004-01-22 | Creavis Gesellschaft Für Technologie Und Innovation Mbh | Polymerzusammensetzung aus Polymeren und ionischen Flüssigkeiten |
| WO2004005391A1 (de) * | 2002-07-05 | 2004-01-15 | Creavis Gesellschaft Für Technologie Und Innovation Mbh | Polymerzusammensetzungen aus polymeren und ionischen flüssigkeiten |
| WO2005007657A2 (de) | 2003-07-11 | 2005-01-27 | Solvay Fluor Gmbh | Verwendung von dbn und dbu-salzen als ionische flüssigkeiten |
| EP1648845B1 (de) | 2003-07-21 | 2008-05-14 | Basf Se | Verfahren zur extraktion von verunreinigungen mit ionischen flüssigkeiten |
| AU2003904323A0 (en) | 2003-08-13 | 2003-08-28 | Viridian Chemical Pty Ltd | Solvents based on salts of aryl acids |
| FI115835B (fi) | 2003-08-15 | 2005-07-29 | Kemira Oyj | Liuotusmenetelmä |
| US7888412B2 (en) | 2004-03-26 | 2011-02-15 | Board Of Trustees Of The University Of Alabama | Polymer dissolution and blend formation in ionic liquids |
| US7534846B2 (en) * | 2004-08-24 | 2009-05-19 | Bridgestone Corporation | Onium-modified polymer and method for manufacturing same |
| DE102004053662A1 (de) | 2004-11-03 | 2006-05-04 | Basf Ag | Verfahren zur Herstellung von Polyisocyanaten |
| JP2006249166A (ja) * | 2005-03-09 | 2006-09-21 | Nippon Synthetic Chem Ind Co Ltd:The | 芳香族ポリイミドの製造方法 |
| CN101522985B (zh) | 2006-10-13 | 2013-01-16 | 巴斯夫欧洲公司 | 增溶聚合物的离子液体 |
| JP2009167362A (ja) * | 2008-01-21 | 2009-07-30 | Sanyo Chem Ind Ltd | マイクロ波重合性組成物 |
| KR101699558B1 (ko) | 2008-08-14 | 2017-02-13 | 바스프 에스이 | 폴리아미드를 제조하기 위한 회분식 방법 |
-
2009
- 2009-02-06 WO PCT/EP2009/051385 patent/WO2009101032A1/de not_active Ceased
- 2009-02-06 EP EP09709916A patent/EP2252397A1/de not_active Withdrawn
- 2009-02-06 JP JP2010545483A patent/JP5599726B2/ja not_active Expired - Fee Related
- 2009-02-06 MX MX2010008671A patent/MX2010008671A/es unknown
- 2009-02-06 KR KR1020107017746A patent/KR20100126678A/ko not_active Ceased
- 2009-02-06 CA CA2713781A patent/CA2713781A1/en not_active Abandoned
- 2009-02-06 US US12/867,110 patent/US8618225B2/en not_active Expired - Fee Related
- 2009-02-06 CN CN2009801047375A patent/CN101970108B/zh not_active Expired - Fee Related
- 2009-02-06 BR BRPI0908350A patent/BRPI0908350A2/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MX2010008671A (es) | 2010-09-24 |
| EP2252397A1 (de) | 2010-11-24 |
| WO2009101032A1 (de) | 2009-08-20 |
| BRPI0908350A2 (pt) | 2015-10-27 |
| CN101970108A (zh) | 2011-02-09 |
| KR20100126678A (ko) | 2010-12-02 |
| JP2011525935A (ja) | 2011-09-29 |
| US8618225B2 (en) | 2013-12-31 |
| CA2713781A1 (en) | 2009-08-20 |
| US20100311918A1 (en) | 2010-12-09 |
| CN101970108B (zh) | 2013-07-10 |
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