JP2016509092A - 新規なポリアミド、調製方法および使用 - Google Patents
新規なポリアミド、調製方法および使用 Download PDFInfo
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- JP2016509092A JP2016509092A JP2015551116A JP2015551116A JP2016509092A JP 2016509092 A JP2016509092 A JP 2016509092A JP 2015551116 A JP2015551116 A JP 2015551116A JP 2015551116 A JP2015551116 A JP 2015551116A JP 2016509092 A JP2016509092 A JP 2016509092A
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- Prior art keywords
- formula
- polyamide
- acid
- monomers
- group
- Prior art date
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- 229920002647 polyamide Polymers 0.000 title claims abstract description 80
- 239000004952 Polyamide Substances 0.000 title claims abstract description 79
- 238000002360 preparation method Methods 0.000 title claims description 20
- 239000000178 monomer Substances 0.000 claims abstract description 56
- 238000000034 method Methods 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000000654 additive Substances 0.000 claims description 13
- 238000001125 extrusion Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 150000004985 diamines Chemical class 0.000 claims description 12
- 238000006068 polycondensation reaction Methods 0.000 claims description 12
- 230000008569 process Effects 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 238000001746 injection moulding Methods 0.000 claims description 9
- 150000003951 lactams Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000000071 blow moulding Methods 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- 239000012763 reinforcing filler Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000007924 injection Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 238000009987 spinning Methods 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 229920006017 homo-polyamide Polymers 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 235000012438 extruded product Nutrition 0.000 claims 1
- -1 C 5 sugars Chemical class 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 229920002292 Nylon 6 Polymers 0.000 description 17
- 229920000642 polymer Polymers 0.000 description 14
- 125000003277 amino group Chemical group 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 11
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 10
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000008188 pellet Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000004753 textile Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- HDJLSECJEQSPKW-UHFFFAOYSA-N Methyl 2-Furancarboxylate Chemical compound COC(=O)C1=CC=CO1 HDJLSECJEQSPKW-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000002518 antifoaming agent Substances 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000006224 matting agent Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- JJMDCOVWQOJGCB-UHFFFAOYSA-N 5-aminopentanoic acid Chemical compound [NH3+]CCCCC([O-])=O JJMDCOVWQOJGCB-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000004609 Impact Modifier Substances 0.000 description 4
- 229910010413 TiO 2 Inorganic materials 0.000 description 4
- 239000001361 adipic acid Substances 0.000 description 4
- 235000011037 adipic acid Nutrition 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000006085 branching agent Substances 0.000 description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229920002302 Nylon 6,6 Polymers 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002240 furans Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000004806 packaging method and process Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 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 2
- GUOSQNAUYHMCRU-UHFFFAOYSA-N 11-Aminoundecanoic acid Chemical compound NCCCCCCCCCCC(O)=O GUOSQNAUYHMCRU-UHFFFAOYSA-N 0.000 description 2
- TUGAQVRNALIPHY-UHFFFAOYSA-N 2,2-dimethylpentane-1,5-diamine Chemical compound NCC(C)(C)CCCN TUGAQVRNALIPHY-UHFFFAOYSA-N 0.000 description 2
- YXOKJIRTNWHPFS-UHFFFAOYSA-N 2,5-dimethylhexane-1,6-diamine Chemical compound NCC(C)CCC(C)CN YXOKJIRTNWHPFS-UHFFFAOYSA-N 0.000 description 2
- SLWIPPZWFZGHEU-UHFFFAOYSA-N 2-[4-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=C(CC(O)=O)C=C1 SLWIPPZWFZGHEU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BUGIFNPYQVKODR-UHFFFAOYSA-N 2-methylhexane-1,6-diamine Chemical compound NCC(C)CCCCN BUGIFNPYQVKODR-UHFFFAOYSA-N 0.000 description 2
- GAGWMWLBYJPFDD-UHFFFAOYSA-N 2-methyloctane-1,8-diamine Chemical compound NCC(C)CCCCCCN GAGWMWLBYJPFDD-UHFFFAOYSA-N 0.000 description 2
- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- WTKWFNIIIXNTDO-UHFFFAOYSA-N 3-isocyanato-5-methyl-2-(trifluoromethyl)furan Chemical compound CC1=CC(N=C=O)=C(C(F)(F)F)O1 WTKWFNIIIXNTDO-UHFFFAOYSA-N 0.000 description 2
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 2
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 2
- 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
- CARJPEPCULYFFP-UHFFFAOYSA-N 5-Sulfo-1,3-benzenedicarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(S(O)(=O)=O)=C1 CARJPEPCULYFFP-UHFFFAOYSA-N 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
- DZCPFKFMCCYUOU-UHFFFAOYSA-N 5-methylnonane-1,1-diamine Chemical compound CCCCC(C)CCCC(N)N DZCPFKFMCCYUOU-UHFFFAOYSA-N 0.000 description 2
- BJLUCDZIWWSFIB-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)(C)C1=CC(C(O)=O)=CC(C(O)=O)=C1 BJLUCDZIWWSFIB-UHFFFAOYSA-N 0.000 description 2
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
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- VWPQCOZMXULHDM-UHFFFAOYSA-N 9-aminononanoic acid Chemical compound NCCCCCCCCC(O)=O VWPQCOZMXULHDM-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 2
- VKLGKDZCKSMSHG-UHFFFAOYSA-N [5-(aminomethyl)furan-2-yl]methanamine Chemical compound NCC1=CC=C(CN)O1 VKLGKDZCKSMSHG-UHFFFAOYSA-N 0.000 description 2
- XEXIPRQHXNUUAA-UHFFFAOYSA-N [5-(aminomethyl)oxolan-2-yl]methanamine Chemical compound NCC1CCC(CN)O1 XEXIPRQHXNUUAA-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229960002684 aminocaproic acid Drugs 0.000 description 2
- 229920006020 amorphous polyamide Polymers 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
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- 238000000113 differential scanning calorimetry Methods 0.000 description 2
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- 239000012808 vapor phase Substances 0.000 description 2
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- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 0 *C(C1OC(CN*)CC1)=O Chemical compound *C(C1OC(CN*)CC1)=O 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-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
- WAXJSQREIWGYCB-UHFFFAOYSA-N 2-[4-(carboxymethyl)cyclohexyl]acetic acid Chemical compound OC(=O)CC1CCC(CC(O)=O)CC1 WAXJSQREIWGYCB-UHFFFAOYSA-N 0.000 description 1
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 description 1
- LTZQJVGOFCCDQA-UHFFFAOYSA-N 3-methylhexane-1,6-diamine Chemical compound NCCC(C)CCCN LTZQJVGOFCCDQA-UHFFFAOYSA-N 0.000 description 1
- RZMLFDPCVRKIQV-UHFFFAOYSA-N 5-(aminomethyl)oxolane-2-carboxylic acid Chemical compound NCC1CCC(C(O)=O)O1 RZMLFDPCVRKIQV-UHFFFAOYSA-N 0.000 description 1
- MNYUSIQFKHKEQT-UHFFFAOYSA-N 8-oxa-3-azabicyclo[3.2.1]octan-4-one Chemical compound O=C1NCC2CCC1O2 MNYUSIQFKHKEQT-UHFFFAOYSA-N 0.000 description 1
- 241001133760 Acoelorraphe Species 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
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- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
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- 239000004606 Fillers/Extenders Substances 0.000 description 1
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 229910021536 Zeolite Inorganic materials 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
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 229920006021 bio-based polyamide Polymers 0.000 description 1
- 229920013724 bio-based polymer Polymers 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
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- 238000011437 continuous method Methods 0.000 description 1
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- 238000007796 conventional method Methods 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- QVGONMHQKGSFOB-UHFFFAOYSA-N methyl 11-aminoundecanoate Chemical compound COC(=O)CCCCCCCCCCN QVGONMHQKGSFOB-UHFFFAOYSA-N 0.000 description 1
- NDBSIOZEOQUDBF-UHFFFAOYSA-N methyl 12-aminododecanoate Chemical compound COC(=O)CCCCCCCCCCCN NDBSIOZEOQUDBF-UHFFFAOYSA-N 0.000 description 1
- TZJVWRXHKAXSEA-UHFFFAOYSA-N methyl 6-aminohexanoate Chemical compound COC(=O)CCCCCN TZJVWRXHKAXSEA-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- AALDQTZAUCUUNZ-UHFFFAOYSA-N nonane-1,1,1,9-tetramine Chemical compound NCCCCCCCCC(N)(N)N AALDQTZAUCUUNZ-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229920006119 nylon 10T Polymers 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920006131 poly(hexamethylene isophthalamide-co-terephthalamide) Polymers 0.000 description 1
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 description 1
- 229920006128 poly(nonamethylene terephthalamide) Polymers 0.000 description 1
- 229920006375 polyphtalamide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- GMRIOAVKKGNMMV-UHFFFAOYSA-N tetrabutylazanium;azide Chemical compound [N-]=[N+]=[N-].CCCC[N+](CCCC)(CCCC)CCCC GMRIOAVKKGNMMV-UHFFFAOYSA-N 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-N tetrahydro-2-furoic acid Chemical compound OC(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-N 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910000166 zirconium phosphate Inorganic materials 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical compound [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
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- 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
- C08G69/40—Polyamides containing oxygen in the form of ether groups
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- 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
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- 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
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- 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
- C08G69/36—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino acids, 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
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
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- 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
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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- 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
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J2377/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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- Manufacturing & Machinery (AREA)
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- Engineering & Computer Science (AREA)
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Abstract
Description
[上式中、
R1が水素原子または式−C(=O)R’の基(R’が1〜4個の炭素原子を有するアルキル基である)であり、
R2が塩素原子または式−OR’’の基(R’’が水素原子または炭化水素基であり、R’’が1〜4個の炭素原子を有するアルキル基である)である]に相当する少なくとも2つの同一または異なるモノマーの間の重縮合反応を含む。
− ジカルボン酸、例えば4〜22個の炭素原子を特に含む脂肪族、脂環式または芳香族ジカルボン酸、例えばコハク酸、グルタル酸、アジピン酸、スベリン酸、アゼライン酸、セバシン酸、1,12−ドデカン二酸;1,3−または1,4−シクロヘキサンジカルボン酸(シス/トランス、またはシスまたはトランス);1,3−または1,4−フェニレン二酢酸;1,3−または1,4−シクロヘキサン二酢酸;イソフタル酸;5−ヒドロキシイソフタル酸;テレフタル酸;4,4’−ベンゾフェノンジカルボン酸;2,6−ナフタレンジカルボン酸;2,5−テトラヒドロフランジカルボン酸(シス/トランス、またはシスまたはトランス)および5−(t−ブチル)イソフタル酸の他、5−スルホイソフタル酸のアルカリ金属(Li、NaまたはK)塩、ならびにPripolの名称で公知のC36脂肪酸二量体;
− ジアミン、例えば4〜22個の炭素原子を特に含む脂肪族、脂環式または芳香族ジアミン、例えばヘキサメチレンジアミン;1,4−ジアミノブタン;1,5−ジアミノペンタン;2−メチル−1,5−ジアミノペンタン;2−メチルヘキサメチレンジアミン;3−メチルヘキサメチレンジアミン;2,5−ジメチルヘキサメチレンジアミン;2,2−ジメチルペンタメチレンジアミン;1,7−ジアミノヘプタン;1,8−ジアミノオクタン;1,9−ジアミノノナンジアミン;2−メチル−1,8−オクタンジアミン;5−メチルノナンジアミン;1,10−ジアミノデカン;1,11−ジアミノウンデカン;1,12−ジアミノドデカン;2,2,4−および2,4,4−トリメチルヘキサメチレンジアミン;2,2,7,7−テトラメチルオクタメチレンジアミン;メタ−キシリレンジアミン;パラ−キシリレンジアミン;イソホロンジアミン;4,4’−ジアミノジフェニルメタン;4,4’−メチレンビス(シクロヘキシルアミン);1個以上のアルキル基で置換され得るC2−C16脂肪族ジアミン;Priamineの名称で公知の脂肪酸二量体由来のC36ジアミン;2,5−ビス(アミノメチル)フランおよび2,5−ビス(アミノメチル)テトラヒドロフラン(シス/トランス、またはシスまたはトランス);パラ−フェニレンジアミン;メタ−フェニレンジアミン;およびJeffamineまたはElastamineの名称で公知のエトキシ化ジアミン(エチレングリコールおよび/またはプロピレングリコールおよび/またはテトラメチレングリコールエーテルを含むポリエーテルジアミン);
− 4〜22個の炭素原子を特に含む他のアミノ酸またはラクタム、例えばカプロラクタム、6−アミノヘキサン酸、5−アミノペンタン酸、7−アミノへプタン酸、9−アミノノナン酸、11−アミノウンデカン酸またはドデカノラクタム;および
− 4〜22個の炭素原子を特に含む他のアミノエステル、メチル6−アミノヘキサノエート、メチル11−アミノウンデカノエート、およびメチル12−アミノドデカノエート。
− PA THF/6(カプロラクタムと式II(特にR1=HおよびR2=OH)、または式IIIのモノマーとから合成された)、
− PA THF/11(11−アミノウンデカン酸と式II(特にR1=HおよびR2=OH)、または式IIIのモノマーとから合成された)
− PA THF/12(ドデカノラクタムと式II(特にR1=HおよびR2=OH)、または式IIIのモノマーとから合成された)
− PA THF/66 特に上に記載された比率において(式II(特にR1=HおよびR2=OH)、または式IIIのモノマーと理論量のアジピン酸およびヘキサメチレンジアミンから特に構成されたナイロン塩とから合成された)
− PA THF/66/6(カプロラクタムと、理論量のアジピン酸およびヘキサメチレンジアミンから特に構成されたナイロン塩と、式II(特にR1=Hおよび2=OH)、特にまたは式IIIのモノマーとから合成された)であり得る。
− アルカリ金属またはアルカリ土類金属カルボキシレート、R2が−OR’’(R’’が水素原子である)である場合には、水素原子はイオン結合によって例えばLi、NaまたはKなどのアルカリ金属またはアルカリ土類金属によって置換される、および/または
− アンモニウム塩、例えば−NH2R1 +X−(Xが例えば塩素などのハロゲンである)であり得ることは理解されよう。
[上式中、
R1が水素原子または式−C(=O)R’の基(R’が1〜4個の炭素原子を有するアルキル基である)であり、
R2が塩素原子または式−OR’’の基(R’’が水素原子または炭化水素基であり、R’’が1〜4個の炭素原子を有するアルキル基である)である]に相当する少なくとも2つの同一または異なるモノマーの間の重縮合反応を含む、本発明によるポリアミドの調製方法である。
段階1 メチル5−(クロロメチル)フラン−2−カルボキシレート1の調製
無水塩化亜鉛(18.74g、0.1375モル)およびパラホルムアルデヒド(16.31g、0.715モル)をジクロロメタン(250ml)中のメチル2−フロエート(63.05g、0.5モル)の溶液に添加する。
1H NMR(400MHz,CDCl3):d=7.13(d,J=3.6Hz,1H),6.49(d,J=3.6Hz,1H),4.59(s,2H),3.90(s,3H).
MS:(M+H m/z=175.1)
DMSO(200ml)中の段階1からの生成物(34.8g、0.2モル、1.0eq)とアジ化ナトリウム(NaN3)(20.0g、0.3モル、1.5eq)との溶液を50℃において16時間にわたって加熱する。反応混合物を氷冷水(1000ml)上に流し込み、石油エーテル(2×500ml)で抽出し、次に、総合抽出物を乾燥させ、真空下で濃縮する。アジド生成物は黄色油(36.0g、収量99%、純度96%)の形態で得られ、他の精製を行なわずに以下の段階で使用される。
1H NMR(400MHz,CDCl3):d=7.15(d,J=3.2Hz,1H),6.46(d,J=3.2Hz,1H),4.38(s,2H),3.90(s,3H).
MS:(M+H m/z=182.1)
メタノール(250ml)中の段階2からの粗原料生成物(25.0g、0.138モル)、ジ(t−ブチル)ジカーボネート(27.0g、0.124モル)およびRh/C(5%、1g)の混合物を500mlのParrオートクレーブに導入する。反応器を周囲温度(約20℃)において36時間にわたって水素圧力(5atm)下に置く。反応混合物をセライトを通して濾過し、黄色油を得るために濾液を真空下で濃縮する。粗原料生成物を、石油エーテル/エチルアセテート(5/1)混合物を使用してシリカカラム上のクロマトグラフィーによって精製する。そのとき、無色の油が得られる(24.0g、収量68%、純度>97%)。
1H NMR(400MHz,CDCl3):d=7.06(d,J=3.6Hz,1H),6.31(d,J=2.8Hz,1H),5.10(s,1H),4.31(d,J=4.8Hz,2H),3.84(s,3H),1.40(s,9H).
MS:(M+H m/z=256.1)
段階3からの生成物(24.0g、94.1mmol)、パラジウム担持木炭(10%w/w、2.5g)およびメタノール(250ml)を500mlのオートクレーブ内に導入する。混合物を16時間にわたって30℃において水素圧力(10atm)下に置く。反応混合物をセライトを通して濾過し、濾液を真空下で濃縮する。無色の油が得られる(20.0g、収量82%、純度>97%)。
MS:(M+Na m/z=282.1)
段階4において得られた生成物(20.0g、77.2mmol)をメタノール(150ml)中に溶解し、気体塩酸を4時間にわたって溶液中に通気する。無色の油を得るために混合物を真空下で濃縮する(14.0g、収量93%、純度>98%)。
1H NMR(400MHz,CD3OD):d=4.63(dd,J=8.8,4.3Hz,1H),4.36−4.33(m,1H),3.78(s,3H),3.21−3.17(m,1H),3.10−3.07(m,1H),2.44−2.39(m,1H),2.18−2.12(m,2H),1.79−1.76(m,1H)
MS:(M+H m/z=160.1)
2グラムの油状のモノマー5を、撹拌せずに窒素ヘッドスペースでフラッシュされた大気圧のガラス管内に置く。その後、それを40℃に調節された金属槽内に浸漬し、2時間にわたって200℃まで徐々に加熱する。ガラス管を40℃の槽内に置くとすぐに沸騰を示す。媒体の粘度は、反応媒体の加熱中に増加する。温度が200℃に達するとき、ガラス管を槽から取り出し、さらに窒素でフラッシングしながら周囲温度まで冷却する。形成されたポリアミドは透明かつ軟質である。
ポリアミド6を合成するようになっている反応器内にカプロラクタム75.09g(0.664モル)、(メチル5−(アミノメチル)テトラヒドロフラン−2−カルボン酸塩酸塩の加水分解によって調製された)5−(アミノメチル)テトラヒドロフラン−2−カルボン酸6.90g(0.048モル)、水36.35gおよび消泡剤1gを導入する。
Claims (14)
- 式Iの前記反復単位から完全になるホモポリアミドであることを特徴とする、請求項1に記載のポリアミド。
- 式Iの前記単位と異なる他の反復単位を含むコポリマーであって、式Iの前記単位と異なる前記反復単位がジカルボン酸、ジアミン、アミノ酸、アミノエステルおよび/またはラクタムなどのコモノマーから得られることを特徴とする、請求項1に記載のポリアミド。
- 前記コポリマーが、前記コポリマーの調製のために導入されたモノマーの全量に基づいて計算された、式Iの反復単位0.5〜10モル%を含むことを特徴とする、請求項3に記載のポリアミド。
- 前記コポリマーが、PA THF/6、PA THF/11、PA THF/12、PA THF/66、およびPA THF/66/6からなる群から選択されることを特徴とする、請求項1〜4のいずれか一項に記載のポリアミド。
- R1が水素原子であり、R2が−OR’’基(R’’が水素原子である)であることを特徴とする、請求項6に記載の方法。
- R1が水素原子であり、R2が−OR’’基(R’’が1〜4個の炭素原子を含む直鎖または分岐アルキル基である)であることを特徴とする、請求項7に記載の方法。
- R’’が、以下の基:メチル、エチル、プロピル、イソプロピル、ブチルおよびイソブチルから選択されることを特徴とする、請求項8に記載の方法。
- 式IIまたはIIIの前記モノマーの少なくとも1つが標準ASTM D6866に従ったバイオベースであることを特徴とする、請求項6〜9のいずれか一項に記載の方法。
- 式IIの前記モノマーの少なくとも1つが塩の形態であることを特徴とする、請求項6〜10のいずれか一項に記載の方法。
- 成形、射出成形、射出/ブロー成形、押出/ブロー成形、押出または紡糸による物品の製造のための、請求項1〜5のいずれか一項に記載のポリアミドの使用。
- 前記物品が成形品または押出品、糸、繊維、フィラメントまたはフィルムであることを特徴とする、請求項1〜5のいずれか一項に記載のポリアミドから得られる物品。
- 請求項1〜5のいずれか一項で定義されるポリアミドと、任意選択により補強充填剤および/または様々な添加剤とを少なくとも含む組成物。
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