CA1145098A - Process for the preparation of amide-containing polymers - Google Patents
Process for the preparation of amide-containing polymersInfo
- Publication number
- CA1145098A CA1145098A CA000348827A CA348827A CA1145098A CA 1145098 A CA1145098 A CA 1145098A CA 000348827 A CA000348827 A CA 000348827A CA 348827 A CA348827 A CA 348827A CA 1145098 A CA1145098 A CA 1145098A
- Authority
- CA
- Canada
- Prior art keywords
- beta
- alpha
- polymer
- water
- ammonium salt
- 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
- 229920000642 polymer Polymers 0.000 title claims abstract description 82
- 150000001408 amides Chemical class 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 title claims description 96
- 230000008569 process Effects 0.000 title claims description 85
- 238000002360 preparation method Methods 0.000 title description 7
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 90
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 61
- WPKYZIPODULRBM-UHFFFAOYSA-N azane;prop-2-enoic acid Chemical compound N.OC(=O)C=C WPKYZIPODULRBM-UHFFFAOYSA-N 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 229910021529 ammonia Inorganic materials 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 23
- 229920002554 vinyl polymer Polymers 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 22
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims description 17
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 9
- 229940000635 beta-alanine Drugs 0.000 claims description 9
- 239000003112 inhibitor Substances 0.000 claims description 9
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- DZGUJOWBVDZNNF-UHFFFAOYSA-N azanium;2-methylprop-2-enoate Chemical compound [NH4+].CC(=C)C([O-])=O DZGUJOWBVDZNNF-UHFFFAOYSA-N 0.000 claims description 4
- 238000000354 decomposition reaction Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract description 5
- 239000000835 fiber Substances 0.000 abstract description 2
- 239000010408 film Substances 0.000 abstract description 2
- 229920003023 plastic Polymers 0.000 abstract description 2
- 239000004033 plastic Substances 0.000 abstract description 2
- 229920005989 resin Polymers 0.000 abstract description 2
- 239000011347 resin Substances 0.000 abstract description 2
- 238000012644 addition polymerization Methods 0.000 abstract 1
- 238000000465 moulding Methods 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 description 50
- 229920002647 polyamide Polymers 0.000 description 49
- 238000006243 chemical reaction Methods 0.000 description 40
- 238000006116 polymerization reaction Methods 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000007789 gas Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 21
- 238000001816 cooling Methods 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000007792 addition Methods 0.000 description 15
- 239000012153 distilled water Substances 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
- 229940048053 acrylate Drugs 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 241001072332 Monia Species 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229940117913 acrylamide Drugs 0.000 description 4
- 238000007259 addition reaction Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000003828 vacuum filtration Methods 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- 229920003188 Nylon 3 Polymers 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003708 ampul Substances 0.000 description 3
- HMQGJGGUWFSPDQ-SQQVDAMQSA-N azanium;(e)-but-2-enoate Chemical compound [NH4+].C\C=C\C([O-])=O HMQGJGGUWFSPDQ-SQQVDAMQSA-N 0.000 description 3
- 229960004132 diethyl ether Drugs 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012258 stirred mixture Substances 0.000 description 3
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
- 229920003176 water-insoluble polymer Polymers 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- BCGCCTGNWPKXJL-UHFFFAOYSA-N 3-(2-cyanoethoxy)propanenitrile Chemical compound N#CCCOCCC#N BCGCCTGNWPKXJL-UHFFFAOYSA-N 0.000 description 1
- WSGYTJNNHPZFKR-UHFFFAOYSA-N 3-hydroxypropanenitrile Chemical compound OCCC#N WSGYTJNNHPZFKR-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
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 1
- 102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241001547070 Eriodes Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CVTZKFWZDBJAHE-UHFFFAOYSA-N [N].N Chemical compound [N].N CVTZKFWZDBJAHE-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010420 art technique Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- AGSPXMVUFBBBMO-UHFFFAOYSA-N beta-aminopropionitrile Chemical compound NCCC#N AGSPXMVUFBBBMO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 description 1
- BQVVSSAWECGTRN-UHFFFAOYSA-L copper;dithiocyanate Chemical compound [Cu+2].[S-]C#N.[S-]C#N BQVVSSAWECGTRN-UHFFFAOYSA-L 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229940052303 ethers for general anesthesia Drugs 0.000 description 1
- KVFIJIWMDBAGDP-UHFFFAOYSA-N ethylpyrazine Chemical compound CCC1=CN=CC=N1 KVFIJIWMDBAGDP-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007792 gaseous phase Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- -1 nitrogen containing hetero-cyclic radicals Chemical class 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32,327 | 1979-04-23 | ||
| US06/032,327 US4283524A (en) | 1979-04-23 | 1979-04-23 | Process for polymerization of composition comprising (1) alpha,beta-unsaturated monocarboxylic acid or ammonium salt thereof and (2) ammonia |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1145098A true CA1145098A (en) | 1983-04-19 |
Family
ID=21864346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000348827A Expired CA1145098A (en) | 1979-04-23 | 1980-03-31 | Process for the preparation of amide-containing polymers |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4283524A (OSRAM) |
| EP (1) | EP0020013B1 (OSRAM) |
| JP (1) | JPS55144025A (OSRAM) |
| KR (1) | KR840000089B1 (OSRAM) |
| AR (1) | AR227885A1 (OSRAM) |
| AT (1) | AT371825B (OSRAM) |
| AU (1) | AU529944B2 (OSRAM) |
| BR (1) | BR8002355A (OSRAM) |
| CA (1) | CA1145098A (OSRAM) |
| DD (1) | DD151178A5 (OSRAM) |
| DE (1) | DE3063655D1 (OSRAM) |
| DK (1) | DK159080A (OSRAM) |
| EG (1) | EG14699A (OSRAM) |
| ES (1) | ES490760A0 (OSRAM) |
| FI (1) | FI67717C (OSRAM) |
| GR (1) | GR68057B (OSRAM) |
| IE (1) | IE49762B1 (OSRAM) |
| IL (1) | IL59751A (OSRAM) |
| IN (1) | IN153986B (OSRAM) |
| MX (1) | MX152995A (OSRAM) |
| NO (1) | NO152876C (OSRAM) |
| PL (1) | PL223648A1 (OSRAM) |
| PT (1) | PT71121A (OSRAM) |
| ZA (1) | ZA802001B (OSRAM) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4590251A (en) * | 1980-08-04 | 1986-05-20 | The Standard Oil Company | Process for the preparation of polyamide from unsaturated nitrile and ammonium salt of unsaturated carboxylic acid |
| US4459394A (en) * | 1981-12-30 | 1984-07-10 | The Standard Oil Company | Preparation of nylon polyamide with cobalt salt |
| EP0086920B1 (en) * | 1982-01-04 | 1986-02-19 | The Standard Oil Company | Catalysts useful for preparing polyamides |
| US4707538A (en) * | 1982-01-04 | 1987-11-17 | The Standard Oil Company | Polyamide preparation with pentaamine cobalt (III) complex catalyst |
| US4525578A (en) * | 1982-01-04 | 1985-06-25 | The Standard Oil Company | Process for the preparation of polyesteramide from cyclic lactone |
| US4429109A (en) | 1982-09-15 | 1984-01-31 | Standard Oil Company | Polyamides with high glass transition temperatures prepared from N,N'-terephthaloyldi-beta-alanine and a diamine |
| US4393192A (en) * | 1982-12-21 | 1983-07-12 | The Standard Oil Company | Crystalline copolymers prepared from N,N'-terephthaloyldi-beta-alanine and a glycol |
| US4625002A (en) * | 1983-01-03 | 1986-11-25 | The Standard Oil Company | Binuclear catalyst for the preparation of polyamide |
| US4628077A (en) * | 1983-12-16 | 1986-12-09 | The Standard Oil Company | Preparation of polyamide with catalyst comprising transition metal attached to a ligand which contains electron withdrawing groups |
| JPS60203636A (ja) * | 1984-03-28 | 1985-10-15 | Fuso Kagaku Kogyo Kk | コポリアミノ酸の製造法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3126353A (en) * | 1964-03-24 | Production of amide-like polycondensa- | ||
| US2146210A (en) * | 1936-11-04 | 1939-02-07 | Du Pont | Synthetic resins |
| US2691643A (en) * | 1950-11-15 | 1954-10-12 | Transparent Package Company | Preparation of polypeptides of beta-alanine |
| US2749331A (en) * | 1952-07-05 | 1956-06-05 | Hercules Powder Co Ltd | Synthetic linear polyamides obtained by the base-catalyzed polymerization of unsaturated amides |
| DE1163541B (de) * | 1961-02-24 | 1964-02-20 | Hoechst Ag | Verfahren zur Herstellung linearer Polyamide hoher Viskositaet aus am Stickstoff unsubstituierten ª-Lactamen |
| US3499879A (en) * | 1965-10-14 | 1970-03-10 | Asahi Chemical Ind | Process for preparing polyamide |
-
1979
- 1979-04-23 US US06/032,327 patent/US4283524A/en not_active Expired - Lifetime
-
1980
- 1980-03-31 CA CA000348827A patent/CA1145098A/en not_active Expired
- 1980-03-31 IL IL59751A patent/IL59751A/xx unknown
- 1980-04-02 AU AU57123/80A patent/AU529944B2/en not_active Ceased
- 1980-04-02 IN IN240/DEL/80A patent/IN153986B/en unknown
- 1980-04-03 ZA ZA00802001A patent/ZA802001B/xx unknown
- 1980-04-15 DK DK159080A patent/DK159080A/da not_active IP Right Cessation
- 1980-04-16 BR BR8002355A patent/BR8002355A/pt unknown
- 1980-04-21 DD DD80220601A patent/DD151178A5/de unknown
- 1980-04-21 GR GR61727A patent/GR68057B/el unknown
- 1980-04-21 PL PL22364880A patent/PL223648A1/xx unknown
- 1980-04-22 AT AT0215080A patent/AT371825B/de not_active IP Right Cessation
- 1980-04-22 FI FI801283A patent/FI67717C/fi not_active IP Right Cessation
- 1980-04-22 NO NO801157A patent/NO152876C/no unknown
- 1980-04-22 MX MX182045A patent/MX152995A/es unknown
- 1980-04-22 IE IE811/80A patent/IE49762B1/en unknown
- 1980-04-22 EP EP80301288A patent/EP0020013B1/en not_active Expired
- 1980-04-22 PT PT71121A patent/PT71121A/pt unknown
- 1980-04-22 AR AR280765A patent/AR227885A1/es active
- 1980-04-22 EG EG242/80A patent/EG14699A/xx active
- 1980-04-22 ES ES490760A patent/ES490760A0/es active Granted
- 1980-04-22 DE DE8080301288T patent/DE3063655D1/de not_active Expired
- 1980-04-23 JP JP5409880A patent/JPS55144025A/ja active Pending
- 1980-04-23 KR KR1019800001653A patent/KR840000089B1/ko not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE800811L (en) | 1980-10-23 |
| ATA215080A (de) | 1982-12-15 |
| PT71121A (en) | 1980-05-01 |
| FI67717B (fi) | 1985-01-31 |
| AU529944B2 (en) | 1983-06-23 |
| MX152995A (es) | 1986-07-16 |
| IL59751A0 (en) | 1980-06-30 |
| AU5712380A (en) | 1980-10-30 |
| KR840000089B1 (ko) | 1984-02-10 |
| EG14699A (en) | 1984-09-30 |
| FI67717C (fi) | 1985-05-10 |
| JPS55144025A (en) | 1980-11-10 |
| EP0020013A1 (en) | 1980-12-10 |
| DD151178A5 (de) | 1981-10-08 |
| ZA802001B (en) | 1981-04-29 |
| IN153986B (OSRAM) | 1984-09-08 |
| US4283524A (en) | 1981-08-11 |
| AR227885A1 (es) | 1982-12-30 |
| FI801283A7 (fi) | 1980-10-24 |
| NO801157L (no) | 1980-10-24 |
| ES8103126A1 (es) | 1981-02-16 |
| DE3063655D1 (en) | 1983-07-14 |
| AT371825B (de) | 1983-08-10 |
| ES490760A0 (es) | 1981-02-16 |
| IE49762B1 (en) | 1985-12-11 |
| NO152876B (no) | 1985-08-26 |
| EP0020013B1 (en) | 1983-06-08 |
| DK159080A (da) | 1980-10-24 |
| KR830002813A (ko) | 1983-05-30 |
| PL223648A1 (OSRAM) | 1981-02-13 |
| GR68057B (OSRAM) | 1981-10-29 |
| IL59751A (en) | 1983-07-31 |
| BR8002355A (pt) | 1980-12-02 |
| NO152876C (no) | 1985-12-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4435548A (en) | Branched polyamidoamines | |
| CA1145098A (en) | Process for the preparation of amide-containing polymers | |
| Cairns et al. | Preparation and properties of N-methylol, N-alkoxymethyl and N-alkylthiomethyl polyamides | |
| EP0800546B1 (en) | Cross-linked polyaspartic acid and salts | |
| US20110054146A1 (en) | Preparation of Low Molecular Weight Polylysine and Polyornithine in High Yield | |
| KR910007526B1 (ko) | 폴리아미드의 제조방법 | |
| CA1090033A (en) | Single step preparation of block copolymer of polyamides | |
| US5391826A (en) | Amidopolyamines derived from amino-carboxylic acid | |
| US2720508A (en) | Polyureidopolyamides | |
| US5239048A (en) | Aromatic polyoxyalkylene amidoamines | |
| US4461885A (en) | Nylon preparation from unsaturated nitrite with amino acid | |
| US4412061A (en) | Process for the preparation of a polyamide from unsaturated nitrile, lactam and water | |
| Jacović et al. | Synthesis of some fumaric acid polyamides from active diester monomers | |
| Reimschuessel et al. | Polyimides. Synthesis and Polymerization of 4-Carboxy-2-piperidone | |
| US4405777A (en) | Preparation of a polyamide from lactam, ammonium salt of unsaturated acid and unsaturated nitrile | |
| Moore et al. | Synthesis of an aliphatic poly (enamino nitrile) analogous to a polyurea | |
| Miller et al. | 9 (10)-Carboxyoctadecylamine and 9 (10)-aminomethyloctadecanoic acid: Synthesis and polymerization to polyamides with lateral substitution | |
| US4590251A (en) | Process for the preparation of polyamide from unsaturated nitrile and ammonium salt of unsaturated carboxylic acid | |
| EP0587997B1 (en) | Fluorine-containing copolyacetals and their preparation | |
| EP0114452B1 (en) | Process for the preparation of a polyamide | |
| US3265667A (en) | Cross-linked polythiourea resins | |
| Abajo et al. | 13C-NMR Sequence Analysis. 23. Synthesis and NMR Spectroscopic Characterization of Polyoxamides with Alternating and Random Sequences of Aliphatic Diamines | |
| Monticelli et al. | Hyperbranched aramids by the A2 þ B3 versus AB2 approach: influence of the reaction conditions on structural development | |
| US4609722A (en) | Process for preparing substantially linear polyamide from N-alkylamide-substituted amine and aqueous ammonia | |
| JP2000063435A (ja) | アリルアミン系重合体の製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |