DE1294020B - Verfahren zur Herstellung von Polyamiden durch Polymerisation von e-Caprolactum - Google Patents
Verfahren zur Herstellung von Polyamiden durch Polymerisation von e-CaprolactumInfo
- Publication number
- DE1294020B DE1294020B DE1957M0036156 DEM0036156A DE1294020B DE 1294020 B DE1294020 B DE 1294020B DE 1957M0036156 DE1957M0036156 DE 1957M0036156 DE M0036156 A DEM0036156 A DE M0036156A DE 1294020 B DE1294020 B DE 1294020B
- Authority
- DE
- Germany
- Prior art keywords
- polymerization
- caprolactam
- activators
- radical
- polymer
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 31
- 230000008569 process Effects 0.000 title claims description 19
- 239000004952 Polyamide Substances 0.000 title claims description 16
- 229920002647 polyamide Polymers 0.000 title claims description 16
- 230000000379 polymerizing effect Effects 0.000 title claims description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 title description 20
- 238000004519 manufacturing process Methods 0.000 title description 6
- 239000003054 catalyst Substances 0.000 claims description 17
- -1 cyclic imides Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000012190 activator Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 238000002845 discoloration Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001805 chlorine compounds Chemical class 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 36
- 229920000642 polymer Polymers 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 20
- 150000003951 lactams Chemical class 0.000 description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 18
- 239000007787 solid Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 230000008901 benefit Effects 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 238000009833 condensation Methods 0.000 description 5
- 230000005494 condensation Effects 0.000 description 5
- 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 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 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 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000001342 alkaline earth metals Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 description 2
- KYEACNNYFNZCST-UHFFFAOYSA-N 1-methylpyrrolidine-2,5-dione Chemical compound CN1C(=O)CCC1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 2
- ZTUKZULGOCFJET-UHFFFAOYSA-N 1-phenylpyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1C1=CC=CC=C1 ZTUKZULGOCFJET-UHFFFAOYSA-N 0.000 description 2
- ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 2-methylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C)C(=O)C2=C1 ZXLYYQUMYFHCLQ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000002386 leaching Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 150000004040 pyrrolidinones Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- QKNHKZFLCNTIFR-UHFFFAOYSA-N 1-(benzenesulfonyl)pyrrolidine-2,5-dione Chemical compound O=C1CCC(=O)N1S(=O)(=O)C1=CC=CC=C1 QKNHKZFLCNTIFR-UHFFFAOYSA-N 0.000 description 1
- FEFQUIPMKBPKAR-UHFFFAOYSA-N 1-benzoylazepan-2-one Chemical compound C=1C=CC=CC=1C(=O)N1CCCCCC1=O FEFQUIPMKBPKAR-UHFFFAOYSA-N 0.000 description 1
- CLFHABXQJQAYEF-UHFFFAOYSA-N 1-benzoylpyrrolidine-2,5-dione Chemical compound C=1C=CC=CC=1C(=O)N1C(=O)CCC1=O CLFHABXQJQAYEF-UHFFFAOYSA-N 0.000 description 1
- LLACJVMQXIZUQI-UHFFFAOYSA-N 1-nitrosopyrrolidine-2,5-dione Chemical compound O=NN1C(=O)CCC1=O LLACJVMQXIZUQI-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- URRQCEAIHXBTJF-UHFFFAOYSA-N 1-phenylpyrrolidine-2,5-dithione Chemical compound C1(=CC=CC=C1)N1C(CCC1=S)=S URRQCEAIHXBTJF-UHFFFAOYSA-N 0.000 description 1
- VVCDDWDDPJXWBF-UHFFFAOYSA-N 1-propanethioylpyrrole-2,5-dione Chemical compound CCC(=S)N1C(=O)C=CC1=O VVCDDWDDPJXWBF-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- FWIKUJWHKZKNCI-UHFFFAOYSA-N 2-acetyl-3a,4,5,7a-tetrahydroisoindole-1,3-dione Chemical compound C(C)(=O)N1C(C2C(C1=O)CCC=C2)=O FWIKUJWHKZKNCI-UHFFFAOYSA-N 0.000 description 1
- SDZZWFIVMZCSIB-UHFFFAOYSA-N 2-benzoylisoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C(=O)C1=CC=CC=C1 SDZZWFIVMZCSIB-UHFFFAOYSA-N 0.000 description 1
- ARJPPNFIEQKVBB-UHFFFAOYSA-N 3-acetamidopropanal Chemical compound CC(=O)NCCC=O ARJPPNFIEQKVBB-UHFFFAOYSA-N 0.000 description 1
- CONKBQPVFMXDOV-QHCPKHFHSA-N 6-[(5S)-5-[[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]methyl]-2-oxo-1,3-oxazolidin-3-yl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C[C@H]1CN(C(O1)=O)C1=CC2=C(NC(O2)=O)C=C1 CONKBQPVFMXDOV-QHCPKHFHSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FFKZOUIEAHOBHW-UHFFFAOYSA-N N,4-dimethyl-N-nitrosobenzenesulfonamide Chemical compound O=NN(C)S(=O)(=O)C1=CC=C(C)C=C1 FFKZOUIEAHOBHW-UHFFFAOYSA-N 0.000 description 1
- VFTZWOZICUIRLX-UHFFFAOYSA-N N-(4-oxopentyl)nitrous amide Chemical compound N(=O)NCCCC(C)=O VFTZWOZICUIRLX-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- BTZXJXLQDHLGSO-UHFFFAOYSA-N N-ethyl-N-ethylsulfonyldodecanamide Chemical compound C(C)N(S(=O)(=O)CC)C(CCCCCCCCCCC)=O BTZXJXLQDHLGSO-UHFFFAOYSA-N 0.000 description 1
- MORRLXIJFMSBNI-UHFFFAOYSA-N N-nitroso-N-(2-phenylethyl)butane-1-sulfonamide Chemical compound N(=O)N(S(=O)(=O)CCCC)CCC1=CC=CC=C1 MORRLXIJFMSBNI-UHFFFAOYSA-N 0.000 description 1
- VBICSBKUORUVEN-UHFFFAOYSA-N O=NNS(=O)=O Chemical class O=NNS(=O)=O VBICSBKUORUVEN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000003950 cyclic amides Chemical class 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000010096 film blowing Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- FQTCUKQMGGJRCU-UHFFFAOYSA-N n,n-diacetylacetamide Chemical compound CC(=O)N(C(C)=O)C(C)=O FQTCUKQMGGJRCU-UHFFFAOYSA-N 0.000 description 1
- DZBVJDAMKGJGRW-UHFFFAOYSA-N n-(benzenesulfonyl)-n-methylacetamide Chemical compound CC(=O)N(C)S(=O)(=O)C1=CC=CC=C1 DZBVJDAMKGJGRW-UHFFFAOYSA-N 0.000 description 1
- DOORLMZWXWAASK-UHFFFAOYSA-N n-(benzenesulfonyl)-n-methylbenzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)N(C)S(=O)(=O)C1=CC=CC=C1 DOORLMZWXWAASK-UHFFFAOYSA-N 0.000 description 1
- BMXLNWWQIJELAW-UHFFFAOYSA-N n-ethyl-n-(4-methylphenyl)sulfonylacetamide Chemical compound CCN(C(C)=O)S(=O)(=O)C1=CC=C(C)C=C1 BMXLNWWQIJELAW-UHFFFAOYSA-N 0.000 description 1
- SRGXUKYSILPYNM-UHFFFAOYSA-N n-ethyl-n-methylsulfonylmethanesulfonamide Chemical compound CCN(S(C)(=O)=O)S(C)(=O)=O SRGXUKYSILPYNM-UHFFFAOYSA-N 0.000 description 1
- UGUJGQMBCAWTEP-UHFFFAOYSA-N n-methyl-n-nitrosobenzenesulfonamide Chemical compound O=NN(C)S(=O)(=O)C1=CC=CC=C1 UGUJGQMBCAWTEP-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- XKLJHFLUAHKGGU-UHFFFAOYSA-N nitrous amide Chemical class ON=N XKLJHFLUAHKGGU-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 125000004436 sodium atom Chemical group 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000008053 sultones Chemical class 0.000 description 1
- 230000002277 temperature effect Effects 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000005406 washing Methods 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US627984A US3017391A (en) | 1956-12-13 | 1956-12-13 | Preparation of polycaprolactam using n-acyl activators |
| US59933858A | 1958-04-21 | 1958-04-21 | |
| US729509A US3018273A (en) | 1958-04-21 | 1958-04-21 | Process of polymerizing higher lactams |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1294020B true DE1294020B (de) | 1969-04-30 |
Family
ID=27416777
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1957M0036156 Pending DE1294020B (de) | 1956-12-13 | 1957-12-12 | Verfahren zur Herstellung von Polyamiden durch Polymerisation von e-Caprolactum |
| DE19571795467 Pending DE1795467A1 (de) | 1956-12-13 | 1957-12-12 | Verfahren zur Herstellung von Polyamiden durch Polymerisieren von epsilon-Caprolactam |
| DE19591420598 Expired DE1420598C3 (de) | 1956-12-13 | 1959-04-18 | Verfahren zur Herstellung von PoIycaprolactam |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19571795467 Pending DE1795467A1 (de) | 1956-12-13 | 1957-12-12 | Verfahren zur Herstellung von Polyamiden durch Polymerisieren von epsilon-Caprolactam |
| DE19591420598 Expired DE1420598C3 (de) | 1956-12-13 | 1959-04-18 | Verfahren zur Herstellung von PoIycaprolactam |
Country Status (7)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4518765A (en) * | 1984-03-19 | 1985-05-21 | The Upjohn Company | Anionic polymerization of lactam with azetidine-2,4-dione promoter |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1107217A (en) * | 1964-04-17 | 1968-03-27 | Licencia Talalmanyokat | Process for polymerizing lactams |
| IT1014528B (it) * | 1973-12-28 | 1977-04-30 | Sir Soc Italiana Resine Spa | Copolimeri a blocchi |
| IT1027885B (it) * | 1974-12-20 | 1978-12-20 | Sir Soc Italiana Resine Spa | Copolimeri a blocchi |
| CA1232993A (en) * | 1982-09-29 | 1988-02-16 | Markus Matzner | Blends of poly(etherimides) and polyamides |
| ES2078181B1 (es) * | 1994-03-04 | 1996-08-01 | Fernandez Rafael Zabala | Proceso de fabricacion de utillaje a partir de caprolactama con un prepolimero para obtener un copolimero en bruto moldeado que se mecaniza con la forma del utillaje deseado. |
| CN110983364A (zh) * | 2019-12-20 | 2020-04-10 | 湖南七纬科技有限公司 | 一种高亲水性电解水用隔膜及其制备方法 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD5385A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| DE927292C (de) * | 1943-03-17 | 1955-05-05 | Thueringische Zellwolle A G | Verfahren zur Herstellung von gemischten linearen Polyamiden |
| GB731294A (en) * | 1951-12-07 | 1955-06-08 | Arnold Hoffman & Co Inc | New linear polyamides |
| GB749332A (en) * | 1953-02-24 | 1956-05-23 | Arnold Hoffman & Co Inc | Improvements in polymerization of cyclic amides |
| GB754944A (en) * | 1953-02-24 | 1956-08-15 | Arnold Hoffman & Co Inc | Improvement in polymerization of cyclic amides |
| DE1062930B (de) * | 1956-11-08 | 1959-08-06 | Basf Ag | Verfahren zur Herstellung von Polymerisationsprodukten aus alpha-Pyrrolidon |
| DE1067591B (de) * | 1956-08-18 | 1959-10-22 | Bayer Ag | Verfahren zur Beschleunigung der ionischen Polymerisation von mehr als sechs Ringglieder enthaltenden Lactamen |
-
0
- CA CA607225A patent/CA607225A/en not_active Expired
- IT IT580069D patent/IT580069A/it unknown
-
1957
- 1957-11-27 FR FR1194451D patent/FR1194451A/fr not_active Expired
- 1957-12-12 GB GB3863857A patent/GB872328A/en not_active Expired
- 1957-12-12 DE DE1957M0036156 patent/DE1294020B/de active Pending
- 1957-12-12 DE DE19571795467 patent/DE1795467A1/de active Pending
-
1959
- 1959-04-18 DE DE19591420598 patent/DE1420598C3/de not_active Expired
- 1959-04-20 CH CH7226059A patent/CH429173A/de unknown
- 1959-04-21 FR FR792729A patent/FR1220726A/fr not_active Expired
- 1959-04-21 NL NL238392A patent/NL125087C/xx active
- 1959-04-21 GB GB1352659A patent/GB916093A/en not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD5385A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| DE927292C (de) * | 1943-03-17 | 1955-05-05 | Thueringische Zellwolle A G | Verfahren zur Herstellung von gemischten linearen Polyamiden |
| GB731294A (en) * | 1951-12-07 | 1955-06-08 | Arnold Hoffman & Co Inc | New linear polyamides |
| GB749332A (en) * | 1953-02-24 | 1956-05-23 | Arnold Hoffman & Co Inc | Improvements in polymerization of cyclic amides |
| GB754944A (en) * | 1953-02-24 | 1956-08-15 | Arnold Hoffman & Co Inc | Improvement in polymerization of cyclic amides |
| DE1030022B (de) * | 1953-02-24 | 1958-05-14 | Gen Aniline & Film Corp | Verfahren zur Herstellung von hochmolekularen Polymerisationsprodukten |
| DE1067591B (de) * | 1956-08-18 | 1959-10-22 | Bayer Ag | Verfahren zur Beschleunigung der ionischen Polymerisation von mehr als sechs Ringglieder enthaltenden Lactamen |
| DE1062930B (de) * | 1956-11-08 | 1959-08-06 | Basf Ag | Verfahren zur Herstellung von Polymerisationsprodukten aus alpha-Pyrrolidon |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4518765A (en) * | 1984-03-19 | 1985-05-21 | The Upjohn Company | Anionic polymerization of lactam with azetidine-2,4-dione promoter |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1420598A1 (de) | 1968-10-10 |
| NL125087C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-09-16 |
| IT580069A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| DE1795467A1 (de) | 1972-01-27 |
| FR1194451A (fr) | 1959-11-10 |
| GB916093A (en) | 1963-01-16 |
| FR1220726A (fr) | 1960-05-27 |
| GB872328A (en) | 1961-07-05 |
| DE1420598C3 (de) | 1973-10-18 |
| CH429173A (de) | 1967-01-31 |
| CA607225A (en) | 1960-10-18 |
| DE1420598B2 (de) | 1973-02-01 |
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