JPS6131431A - 超高分子量ナイロン６の製造法 - Google Patents
超高分子量ナイロン６の製造法Info
- Publication number
- JPS6131431A JPS6131431A JP15310484A JP15310484A JPS6131431A JP S6131431 A JPS6131431 A JP S6131431A JP 15310484 A JP15310484 A JP 15310484A JP 15310484 A JP15310484 A JP 15310484A JP S6131431 A JPS6131431 A JP S6131431A
- Authority
- JP
- Japan
- Prior art keywords
- molecular weight
- compound
- nylon
- mol
- caprolactam
- 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.)
- Granted
Links
- 229920002292 Nylon 6 Polymers 0.000 title claims abstract description 44
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims abstract description 52
- 150000003951 lactams Chemical class 0.000 claims abstract description 16
- 238000005227 gel permeation chromatography Methods 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- -1 acyl lactam Chemical class 0.000 claims description 11
- 150000002680 magnesium Chemical class 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000012719 thermal polymerization Methods 0.000 claims description 2
- 238000000465 moulding Methods 0.000 abstract description 5
- 238000001891 gel spinning Methods 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 230000000379 polymerizing effect Effects 0.000 abstract description 3
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000006116 polymerization reaction Methods 0.000 description 36
- 229920000642 polymer Polymers 0.000 description 22
- 238000000034 method Methods 0.000 description 19
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 10
- 239000007788 liquid Substances 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 4
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 4
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000003672 processing method Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- WMJMABVHDMRMJA-UHFFFAOYSA-M [Cl-].[Mg+]C1CCCCC1 Chemical compound [Cl-].[Mg+]C1CCCCC1 WMJMABVHDMRMJA-UHFFFAOYSA-M 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229940100630 metacresol Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- YGAWUJONOQVQLI-UHFFFAOYSA-N 1,6-bis(2-oxopyrrolidin-1-yl)hexane-1,6-dione Chemical compound C1CCC(=O)N1C(=O)CCCCC(=O)N1CCCC1=O YGAWUJONOQVQLI-UHFFFAOYSA-N 0.000 description 1
- AGEILULECXEYHO-UHFFFAOYSA-N 1,6-bis(7-oxoazepan-2-yl)hexane-1,6-dione Chemical compound C1CCCC(=O)NC1C(=O)CCCCC(=O)C1CCCCC(=O)N1 AGEILULECXEYHO-UHFFFAOYSA-N 0.000 description 1
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 1
- VYXRTZYURDKMLT-UHFFFAOYSA-N 1-benzoylpyrrolidin-2-one Chemical compound C=1C=CC=CC=1C(=O)N1CCCC1=O VYXRTZYURDKMLT-UHFFFAOYSA-N 0.000 description 1
- FAGGUIDTQQXDSJ-UHFFFAOYSA-N 3-benzoylazepan-2-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCNC1=O FAGGUIDTQQXDSJ-UHFFFAOYSA-N 0.000 description 1
- AKTMBWOBVNALDM-UHFFFAOYSA-N 3-butanoylazepan-2-one Chemical compound CCCC(=O)C1CCCCNC1=O AKTMBWOBVNALDM-UHFFFAOYSA-N 0.000 description 1
- RMAZSKRBPBAEEV-UHFFFAOYSA-N 7-[3-chloro-4-(7-oxoazepane-2-carbonyl)benzoyl]azepan-2-one Chemical compound ClC1=C(C(=O)C2CCCCC(=O)N2)C=CC(=C1)C(=O)C1CCCCC(=O)N1 RMAZSKRBPBAEEV-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- CJYXCQLOZNIMFP-UHFFFAOYSA-N azocan-2-one Chemical compound O=C1CCCCCCN1 CJYXCQLOZNIMFP-UHFFFAOYSA-N 0.000 description 1
- YDLSUFFXJYEVHW-UHFFFAOYSA-N azonan-2-one Chemical compound O=C1CCCCCCCN1 YDLSUFFXJYEVHW-UHFFFAOYSA-N 0.000 description 1
- JKRAPJXEWBPBTP-UHFFFAOYSA-M bromo(dipropyl)alumane Chemical compound [Br-].CCC[Al+]CCC JKRAPJXEWBPBTP-UHFFFAOYSA-M 0.000 description 1
- VPCAAUUIFCAFRZ-UHFFFAOYSA-N butylalumane Chemical compound CCCC[AlH2] VPCAAUUIFCAFRZ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003426 co-catalyst 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
- 238000011161 development Methods 0.000 description 1
- RFUDQCRVCDXBGK-UHFFFAOYSA-L dichloro(propyl)alumane Chemical compound [Cl-].[Cl-].CCC[Al+2] RFUDQCRVCDXBGK-UHFFFAOYSA-L 0.000 description 1
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000010035 extrusion spinning Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- QGEFGPVWRJCFQP-UHFFFAOYSA-M magnesium;methanidylbenzene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C1=CC=CC=C1 QGEFGPVWRJCFQP-UHFFFAOYSA-M 0.000 description 1
- DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002899 organoaluminium compounds Chemical class 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 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 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyamides (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15310484A JPS6131431A (ja) | 1984-07-25 | 1984-07-25 | 超高分子量ナイロン６の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP15310484A JPS6131431A (ja) | 1984-07-25 | 1984-07-25 | 超高分子量ナイロン６の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6131431A true JPS6131431A (ja) | 1986-02-13 |
| JPH0119807B2 JPH0119807B2 (enrdf_load_stackoverflow) | 1989-04-13 |
Family
ID=15555057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP15310484A Granted JPS6131431A (ja) | 1984-07-25 | 1984-07-25 | 超高分子量ナイロン６の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6131431A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006518410A (ja) * | 2003-02-21 | 2006-08-10 | デーエスエム アイピー アセッツ ベー． ヴェー． | 溶融加工可能なポリアミド組成物を調製する方法 |
| JP2021504562A (ja) * | 2017-11-28 | 2021-02-15 | ハンファ ソリューションズ コーポレーション | 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 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6344055B2 (ja) * | 2013-05-23 | 2018-06-20 | 株式会社リコー | ポリマーの製造方法 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4832782A (enrdf_load_stackoverflow) * | 1971-09-01 | 1973-05-02 | ||
| JPS60162807A (ja) * | 1984-01-31 | 1985-08-24 | Toyobo Co Ltd | 高強力ナイロン６フイラメントの製造方法 |
-
1984
- 1984-07-25 JP JP15310484A patent/JPS6131431A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4832782A (enrdf_load_stackoverflow) * | 1971-09-01 | 1973-05-02 | ||
| JPS60162807A (ja) * | 1984-01-31 | 1985-08-24 | Toyobo Co Ltd | 高強力ナイロン６フイラメントの製造方法 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006518410A (ja) * | 2003-02-21 | 2006-08-10 | デーエスエム アイピー アセッツ ベー． ヴェー． | 溶融加工可能なポリアミド組成物を調製する方法 |
| JP2021504562A (ja) * | 2017-11-28 | 2021-02-15 | ハンファ ソリューションズ コーポレーション | 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0119807B2 (enrdf_load_stackoverflow) | 1989-04-13 |
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