JP2021504562A - 二重活性基を持つ分子量調節剤を用いたポリアマイド製造方法及びそれにより製造されたポリアマイド - Google Patents
二重活性基を持つ分子量調節剤を用いたポリアマイド製造方法及びそれにより製造されたポリアマイド Download PDFInfo
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- JP2021504562A JP2021504562A JP2020549524A JP2020549524A JP2021504562A JP 2021504562 A JP2021504562 A JP 2021504562A JP 2020549524 A JP2020549524 A JP 2020549524A JP 2020549524 A JP2020549524 A JP 2020549524A JP 2021504562 A JP2021504562 A JP 2021504562A
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- polyamide
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- 239000004952 Polyamide Substances 0.000 title claims abstract description 56
- 229920002647 polyamide Polymers 0.000 title claims abstract description 56
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- 230000009977 dual effect Effects 0.000 title claims abstract description 15
- 238000000034 method Methods 0.000 title abstract description 11
- 239000000463 material Substances 0.000 claims description 32
- 239000003607 modifier Substances 0.000 claims description 25
- 239000012190 activator Substances 0.000 claims description 22
- 150000003951 lactams Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 16
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006116 polymerization reaction Methods 0.000 claims description 12
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims description 11
- 150000001340 alkali metals Chemical class 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 9
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 claims description 9
- 238000010539 anionic addition polymerization reaction Methods 0.000 claims description 9
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 9
- 239000003999 initiator Substances 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- -1 N-acetyl laurolactam Chemical compound 0.000 claims description 7
- 150000004703 alkoxides Chemical class 0.000 claims description 6
- 239000001569 carbon dioxide Substances 0.000 claims description 6
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 6
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 4
- 150000004692 metal hydroxides Chemical class 0.000 claims description 4
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 4
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 4
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 claims description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002537 cosmetic Substances 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 239000012771 household material Substances 0.000 claims description 2
- 239000012567 medical material Substances 0.000 claims description 2
- 230000006583 body weight regulation Effects 0.000 claims 1
- 150000001450 anions Chemical group 0.000 abstract description 5
- 238000007151 ring opening polymerisation reaction Methods 0.000 abstract description 5
- 238000007259 addition reaction Methods 0.000 abstract description 4
- 238000010586 diagram Methods 0.000 abstract 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 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 11
- 239000003054 catalyst Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229910052700 potassium Inorganic materials 0.000 description 7
- 239000011591 potassium Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 5
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 5
- 229910000105 potassium hydride Inorganic materials 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920003235 aromatic polyamide Polymers 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RIGQNOSSTOUWRV-UHFFFAOYSA-N 13-[3-(13-oxo-azacyclotridecane-2-carbonyl)benzoyl]-azacyclotridecan-2-one Chemical compound C=1C=CC(C(=O)C2NC(=O)CCCCCCCCCC2)=CC=1C(=O)C1CCCCCCCCCCC(=O)N1 RIGQNOSSTOUWRV-UHFFFAOYSA-N 0.000 description 2
- 239000004953 Aliphatic polyamide Substances 0.000 description 2
- 0 CC(*)NC(C)CCNC(C(C)(C)C*(C)C(C)=O)=O Chemical compound CC(*)NC(C)CCNC(C(C)(C)C*(C)C(C)=O)=O 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 229920000299 Nylon 12 Polymers 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229920003231 aliphatic polyamide Polymers 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 2
- 229910001623 magnesium bromide Inorganic materials 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 2
- ZBFCSRYSLRPAOY-UHFFFAOYSA-M sodium;hydroxy(phenyl)methanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(O)C1=CC=CC=C1 ZBFCSRYSLRPAOY-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000004260 weight control Methods 0.000 description 2
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-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
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920000572 Nylon 6/12 Polymers 0.000 description 1
- ITGVBNUIFZZBKK-UHFFFAOYSA-N O=C(c1cccc(C(N(CCCCCCCCCCC2)C2=O)=O)c1)N(CCCCCCCCCCC1)C1=O Chemical compound O=C(c1cccc(C(N(CCCCCCCCCCC2)C2=O)=O)c1)N(CCCCCCCCCCC1)C1=O ITGVBNUIFZZBKK-UHFFFAOYSA-N 0.000 description 1
- 206010033546 Pallor Diseases 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- HUFREHBVNZUPKR-UHFFFAOYSA-N [K].CCC Chemical compound [K].CCC HUFREHBVNZUPKR-UHFFFAOYSA-N 0.000 description 1
- YPKOTWSAVCIFAM-UHFFFAOYSA-N [Na].CCC Chemical compound [Na].CCC YPKOTWSAVCIFAM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical group NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000011243 crosslinked material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000013308 plastic optical fiber Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/02—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G69/08—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
- C08G69/20—Anionic polymerisation characterised by the catalysts used
-
- 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
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Abstract
Description
陰イオン重合反応による分子量調節剤を含むポリアマイド製造方法であって、
ラクタム、前記ラクタム全体100重量部に対して、開始剤としてアルカリ金属0.01乃至20重量部、二重活性基を持つ分子量調節剤として下記化学式2で示される化合物0.01乃至5.0重量部、活性化剤0.01乃至5.0重量部を用いた下記化学式1で示される化合物を含むポリアマイド製造方法。
ラクタム、前記ラクタム全体100重量部に対して、開始剤としてアルカリ金属0.01乃至20重量部、二重活性基を持つ分子量調節剤として下記化学式2で示される化合物0.01乃至5.0重量部、活性化剤0.01乃至5.0重量部を用いた下記化学式1で示される化合物を含むことができる、
親電子性部分によってN−置換されたラクタム、脂肪族ジイソシアネート、芳香族ジイソシアネート、2つを超過するイソシアネート基を有するポリイソシアネート、及び脂肪族ジアシルハロゲン化物と芳香族ジアシルハロゲン化物の群より選択される。また、活性化剤(c)としてそれらの混合物からなる群より選択された少なくとも1種以上を含むことができる。
IBL(isophthaloyl−bis−laurolactam)分子量調節提議調節剤の製造
3−neckフラスコにスターラー、環流コンデンサ管と滴下漏斗を設置した。この時全てのガラス器具は水分に敏感な反応物を考慮して窒素雰囲気下に予め乾燥させた。フラスコにモノマーであるラウロラクタム1mol当量(197.32g)、triethylamine 1mol、500ml THFを入れて攪拌させた。ここで、triethylamineはラウロラクタムとisophthaloyl chlorideが反応すると生成される塩酸を捉えるスカベンジャーの役割を行う。上記用意した混合物をかき混ぜながら氷で冷やし150ml THFに0.5mol当量のisophthaloyl chlorideを溶かした溶液を40分間緩やかに滴下した。投入が完了した後に反応混合物を常温で30分の間攪拌させてからフィルタリングした。白色の固体生成物は空気下に乾燥させた後、反応副産物であるEt3NH+Cl−を除去するために200mlの水に入れて攪拌させた。フィルターペーパーの上で100mlの蒸溜水でそれぞれ2回に分けて洗浄した。白色粉末は80℃の真空オーブンで乾燥させDSCと13C−NMRを用いて物質を確認した。
<実施例1>
二重活性基を有する分子量調節剤(IBL)用いたポリアマイドの製造
単量体のカプロラクタムとラウロラクタムと開始剤のNaHのモル比をそれぞれ50:50:1になるように称量した後、3−neckフラスコに入れてオイルバス(oil bath)の温度を160℃に合わせ、窒素雰囲気下にモノマーと開始剤を一次的に溶かした後、反応物がすべて溶けたことを確認した後、真空をかけて反応物に発生した水素気体を除去した。重合反応が実際的に起こる温度230℃に合わせた後、ラクタム全体100モルに対して分子量調節剤0.05モル及び活性化剤TDI0.15モルを投入した。重合が完了するとギ酸と水の1:1の混合溶液を入れて反応を終結させた後、水とアルコールで複数回洗浄した後、真空オーブンで最終乾燥させ、下記表1による含有量を持つ試料を回収した。各試料の相対粘度を確認し、その結果を表2に表した。この時、相対粘度は1、1、1、3、3、3−Hexafluoro−2−propanol(HFIP)に重合体を入れて2wt%溶液を製造して25℃で測定した。
上記表1のように末端封止材0.2モル比を投入した点を除けば実施例1と同じ方法でポリアマイドを製造した。
上記表1のように活性化剤としてTDIの代わりにCO2を投入した点を除けば実施例1と同じ方法でポリアマイドを製造した。
<比較例1>
イソフタロイル−ビス−ラウロラクタム(isophthaloyl−bis−laurolactam)の代わりにイソフタロイル−ビス−カプロラクタム(isophthaloyl−bis−caprolactam)を使用するが、THFの代わりにトルエン(toluene)を使用しラウロラクタム(laurolactam)の代わりにカプロラクタム(caprolactam)を使用して分子量調節剤を製造し、これにより実施例1と同様にポリアマイドを製造した。
イソフタロイル−ビス−ラウロラクタム(isophthaloyl−bis−laurolactam)を添加しない点を除けば実施例1と同様に重合試料を製造した。
Claims (11)
- 前記ラクタムはカプロラクタム、ラウロラクタム、ピロリドン、ピペリジノン及びそれらの混合物を含む群より選ばれる少なくとも1種以上を含む
請求項1に記載の二重活性基を持つ分子量調節剤を用いたポリアマイド製造方法。 - 前記ラクタムのうち選択された2種のラクタムは20〜80:80〜20重量比で含む
請求項2に記載の二重活性基を持つ分子量調節剤を用いたポリアマイド製造方法。 - 前記活性化剤は二酸化炭素(CO2)、ベンゾイルクロリド(benzoyl chloride)、N−アセチルカプロラクタム(N−acetyl caprolactam)、N−アセチルラウロラクタム(N−acetyl laurolactam)、オクタデシルイソシアネート(octadecyl isocyanate(SIC))、トルエンジイソシアネート(toluene diisocyanate(TDI))、ヘキサメチレンジイソシアネート(hexamethylene diisocyanate(HDI))及びそれらの混合物からなる群より選択された1種以上を含む
請求項1に記載の二重活性基を持つ分子量調節剤を用いたポリアマイド製造方法。 - 前記アルカリ金属は金属水素化物(metal hydride)、金属水酸化物(metal hydroxide)及び金属アルコキシド(metal alkoxide)からなる群より選択された少なくとも1種以上を含む
請求項1に記載のアマイド系分子量調節剤を含むポリアマイド製造方法。 - 前記重合温度は160乃至300℃範囲で行われる
請求項1に記載の二重活性基を持つ分子量調節剤を含むポリアマイド製造方法。 - 請求項1ないし6のいずれかに記載のポリアマイド製造方法で製造された
ことを特徴とするポリアマイド。 - 前記ポリアマイドは4以下の分子量分布範囲を持つ
請求項7に記載のポリアマイド。 - 前記ポリアマイドの重量平均分子量(Mw)は20,000乃至100,000g/mol以内の範囲を持つ
請求項7に記載のポリアマイド。 - 前記ポリアマイドは線形、分枝型、超分枝型(hyperbranched)又は樹枝状(denditric)構造である
請求項7に記載のポリアマイド。 - 請求項7によるポリアマイドを含む車両用素材、電子機器用素材、産業用パイプ素材、建築土木用素材、3Dプリンタ用素材、繊維用素材、被服素材、工作機械用素材、医療用素材、航空用素材、太陽光素材、電池用素材、スポーツ用素材、家電用素材、家庭用素材及び化粧品用素材からなる群より選択される
ことを特徴とする部品素材。
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CN111542560A (zh) | 2020-08-14 |
CN111542560B (zh) | 2023-08-25 |
WO2019107756A1 (ko) | 2019-06-06 |
EP3719053A1 (en) | 2020-10-07 |
ES2950758T3 (es) | 2023-10-13 |
JP7091466B2 (ja) | 2022-06-27 |
EP3719053A4 (en) | 2021-09-08 |
US20210002424A1 (en) | 2021-01-07 |
KR102262504B1 (ko) | 2021-06-08 |
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