JPS6140692B2 - - Google Patents
Info
- Publication number
- JPS6140692B2 JPS6140692B2 JP85879A JP85879A JPS6140692B2 JP S6140692 B2 JPS6140692 B2 JP S6140692B2 JP 85879 A JP85879 A JP 85879A JP 85879 A JP85879 A JP 85879A JP S6140692 B2 JPS6140692 B2 JP S6140692B2
- Authority
- JP
- Japan
- Prior art keywords
- caprolactam
- dialkylamino
- polymerization
- catalyst
- present
- 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
Links
- 150000003950 cyclic amides Chemical class 0.000 claims description 8
- 239000004952 Polyamide Substances 0.000 claims description 7
- 229920002647 polyamide Polymers 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 description 20
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 229920001577 copolymer Polymers 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- CFZGIDYCUWFUJR-UHFFFAOYSA-N 3-(dimethylamino)azepan-2-one Chemical compound CN(C)C1CCCCNC1=O CFZGIDYCUWFUJR-UHFFFAOYSA-N 0.000 description 6
- -1 α-methylpropylamino-ε-caprolactam Chemical compound 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QISSLHPKTCLLDL-UHFFFAOYSA-N N-Acetylcaprolactam Chemical compound CC(=O)N1CCCCCC1=O QISSLHPKTCLLDL-UHFFFAOYSA-N 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003426 co-catalyst Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- HQWPLXHWEZZGKY-UHFFFAOYSA-N diethylzinc Chemical compound CC[Zn]CC HQWPLXHWEZZGKY-UHFFFAOYSA-N 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 2
- KRDJNXNRTUJHRK-UHFFFAOYSA-N 1,3-dimethyl-1,3-bis(phenylcarbamoyl)urea Chemical compound C=1C=CC=CC=1NC(=O)N(C)C(=O)N(C)C(=O)NC1=CC=CC=C1 KRDJNXNRTUJHRK-UHFFFAOYSA-N 0.000 description 1
- MFUPLJQNEXUUDW-UHFFFAOYSA-N 2-phenylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1=CC=CC=C1 MFUPLJQNEXUUDW-UHFFFAOYSA-N 0.000 description 1
- SZTYQQPJAPWXLU-UHFFFAOYSA-N 3-(dibutylamino)azepan-2-one Chemical compound CCCCN(CCCC)C1CCCCNC1=O SZTYQQPJAPWXLU-UHFFFAOYSA-N 0.000 description 1
- HHCVJOUNOYDDJX-UHFFFAOYSA-N 3-(diethylamino)azepan-2-one Chemical compound CCN(CC)C1CCCCNC1=O HHCVJOUNOYDDJX-UHFFFAOYSA-N 0.000 description 1
- GUWNZHDVJNHBMU-UHFFFAOYSA-N 3-(dipropylamino)azepan-2-one Chemical compound CCCN(CCC)C1CCCCNC1=O GUWNZHDVJNHBMU-UHFFFAOYSA-N 0.000 description 1
- IGEFUZDZFLHZRZ-UHFFFAOYSA-N 3-(propan-2-ylamino)azepan-2-one Chemical compound CC(C)NC1CCCCNC1=O IGEFUZDZFLHZRZ-UHFFFAOYSA-N 0.000 description 1
- ANZBBKOAUKBPKG-UHFFFAOYSA-N 3-morpholin-4-ylazepan-2-one Chemical compound O=C1NCCCCC1N1CCOCC1 ANZBBKOAUKBPKG-UHFFFAOYSA-N 0.000 description 1
- WZIAZKYQVWGAHM-UHFFFAOYSA-N 3-piperidin-1-ylazepan-2-one Chemical compound O=C1NCCCCC1N1CCCCC1 WZIAZKYQVWGAHM-UHFFFAOYSA-N 0.000 description 1
- QXHLFEWVURXKCP-UHFFFAOYSA-N 3-pyrrolidin-1-ylazepan-2-one Chemical compound O=C1NCCCCC1N1CCCC1 QXHLFEWVURXKCP-UHFFFAOYSA-N 0.000 description 1
- AHCDZZIXAMDCBJ-UHFFFAOYSA-N CCC[Na] Chemical compound CCC[Na] AHCDZZIXAMDCBJ-UHFFFAOYSA-N 0.000 description 1
- ZCUFTCUMEDALHC-UHFFFAOYSA-N CC[K] Chemical compound CC[K] ZCUFTCUMEDALHC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 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
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- PKMBLJNMKINMSK-UHFFFAOYSA-N magnesium;azanide Chemical compound [NH2-].[NH2-].[Mg+2] PKMBLJNMKINMSK-UHFFFAOYSA-N 0.000 description 1
- WRYKIHMRDIOPSI-UHFFFAOYSA-N magnesium;benzene Chemical compound [Mg+2].C1=CC=[C-]C=C1.C1=CC=[C-]C=C1 WRYKIHMRDIOPSI-UHFFFAOYSA-N 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ZNQFZPCFVNOXJQ-UHFFFAOYSA-N n-acetyl-n-methylacetamide Chemical compound CC(=O)N(C)C(C)=O ZNQFZPCFVNOXJQ-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyamides (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP85879A JPS5592736A (en) | 1979-01-05 | 1979-01-05 | Preparation of basic polyamide |
| US06/108,941 US4297477A (en) | 1979-01-05 | 1979-12-31 | Polyamide having --NH--(CH2)4 --CH(NRR')--CO--units |
| EP80100010A EP0013553B1 (en) | 1979-01-05 | 1980-01-03 | Polyamides and a process for their preparation from a substituted epsilon-caprolactam |
| DE8080100010T DE3062647D1 (en) | 1979-01-05 | 1980-01-03 | Polyamides and a process for their preparation from a substituted epsilon-caprolactam |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP85879A JPS5592736A (en) | 1979-01-05 | 1979-01-05 | Preparation of basic polyamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5592736A JPS5592736A (en) | 1980-07-14 |
| JPS6140692B2 true JPS6140692B2 (cs) | 1986-09-10 |
Family
ID=11485346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP85879A Granted JPS5592736A (en) | 1979-01-05 | 1979-01-05 | Preparation of basic polyamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5592736A (cs) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6310494U (cs) * | 1986-07-07 | 1988-01-23 | ||
| JPH01119135U (cs) * | 1988-02-03 | 1989-08-11 | ||
| JPH0514991U (ja) * | 1991-08-03 | 1993-02-26 | オンキヨー株式会社 | 環状発光装置 |
-
1979
- 1979-01-05 JP JP85879A patent/JPS5592736A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6310494U (cs) * | 1986-07-07 | 1988-01-23 | ||
| JPH01119135U (cs) * | 1988-02-03 | 1989-08-11 | ||
| JPH0514991U (ja) * | 1991-08-03 | 1993-02-26 | オンキヨー株式会社 | 環状発光装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5592736A (en) | 1980-07-14 |
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