DE1271985B - Verfahren zur Herstellung von Polyamiden - Google Patents
Verfahren zur Herstellung von PolyamidenInfo
- Publication number
- DE1271985B DE1271985B DEP1271A DE1271985A DE1271985B DE 1271985 B DE1271985 B DE 1271985B DE P1271 A DEP1271 A DE P1271A DE 1271985 A DE1271985 A DE 1271985A DE 1271985 B DE1271985 B DE 1271985B
- Authority
- DE
- Germany
- Prior art keywords
- aminobenzoyl
- chloride
- polyamides
- group
- bromide
- 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
- 239000004952 Polyamide Substances 0.000 title claims description 13
- 229920002647 polyamide Polymers 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000000839 emulsion Substances 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000006068 polycondensation reaction Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 239000003995 emulsifying agent Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims 1
- 230000001588 bifunctional effect Effects 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- -1 aromatic amino acids Chemical class 0.000 description 47
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 7
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 6
- UDJZPTXIRFULJE-UHFFFAOYSA-N 3-aminobenzoyl chloride;hydrochloride Chemical compound Cl.NC1=CC=CC(C(Cl)=O)=C1 UDJZPTXIRFULJE-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000000835 fiber Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- RMDIYHSHNBKVJS-UHFFFAOYSA-N 3-aminobenzoyl chloride Chemical compound NC1=CC=CC(C(Cl)=O)=C1 RMDIYHSHNBKVJS-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- 239000004760 aramid Substances 0.000 description 2
- 229920003235 aromatic polyamide Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
- KDJBKFNZCRDITN-UHFFFAOYSA-N 3-amino-4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1N KDJBKFNZCRDITN-UHFFFAOYSA-N 0.000 description 1
- FVUKYCZRWSQGAS-UHFFFAOYSA-N 3-carbamoylbenzoic acid Chemical compound NC(=O)C1=CC=CC(C(O)=O)=C1 FVUKYCZRWSQGAS-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- RJECQVZUTMEEAD-UHFFFAOYSA-N Br.NC=1C=C(C(=O)Br)C=CC1 Chemical compound Br.NC=1C=C(C(=O)Br)C=CC1 RJECQVZUTMEEAD-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000012696 Interfacial polycondensation Methods 0.000 description 1
- 238000012695 Interfacial polymerization Methods 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- FDQSRULYDNDXQB-UHFFFAOYSA-N benzene-1,3-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=C1 FDQSRULYDNDXQB-UHFFFAOYSA-N 0.000 description 1
- ZKWWAROSTBDFDD-UHFFFAOYSA-N benzenesulfonic acid;hydrobromide Chemical compound Br.OS(=O)(=O)C1=CC=CC=C1 ZKWWAROSTBDFDD-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000004820 halides Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000002166 wet spinning 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
- C08G69/12—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from amino-carboxylic acids with both amino and carboxylic groups aromatically bound
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/30—Polysulfonamides; Polysulfonimides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US146011A US3203933A (en) | 1961-10-18 | 1961-10-18 | Process for preparing polyamides from aromatic amino acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1271985B true DE1271985B (de) | 1968-07-04 |
Family
ID=22515525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP1271A Pending DE1271985B (de) | 1961-10-18 | 1962-07-21 | Verfahren zur Herstellung von Polyamiden |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3203933A (en, 2012) |
| BE (1) | BE620511A (en, 2012) |
| CH (1) | CH454457A (en, 2012) |
| DE (1) | DE1271985B (en, 2012) |
| DK (1) | DK104375C (en, 2012) |
| GB (1) | GB963313A (en, 2012) |
| NL (1) | NL281227A (en, 2012) |
| SE (1) | SE317199B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3472819A (en) * | 1960-05-31 | 1969-10-14 | Du Pont | Polyamides of the recurring benzamide unit |
| US3296213A (en) * | 1963-06-19 | 1967-01-03 | Monsanto Co | Aromatic-aliphatic copolyamides |
| USRE30352E (en) * | 1966-06-13 | 1980-07-29 | E. I. Du Pont De Nemours And Company | Optically anisotropic aromatic polyamide dopes |
| GB1361242A (en) * | 1970-07-08 | 1974-07-24 | Minnesota Mining & Mfg | Laminate comprising non-woven fibrous backing |
| US3905398A (en) * | 1974-04-23 | 1975-09-16 | Moore & Co Samuel | Composite reinforced hose wherein the reinforcing material is braided aromatic polyamide filaments |
| GB1501176A (en) * | 1974-06-03 | 1978-02-15 | Teijin Ltd | Process for preparing aromatic polyamides |
| JPS5130896A (en) * | 1974-09-09 | 1976-03-16 | Sumitomo Chemical Co | Hokozokuhoriamido no seizohoho |
| US4118374A (en) * | 1974-09-09 | 1978-10-03 | Sumitomo Chemical Company, Limited | Production of aromatic polyamides from dicarboxylic acid and diamine |
| US4113537A (en) * | 1974-12-07 | 1978-09-12 | Firma Carl Freudenberg | Heat resistant nonwoven fabric and method of manufacturing same |
| US4025494A (en) * | 1975-09-08 | 1977-05-24 | E. I. Du Pont De Nemours And Company | Process for preparing film- and fiber-forming poly(1,4-benzamide) |
| CN118546356B (zh) * | 2024-07-30 | 2024-11-29 | 烟台泰和新材高分子新材料研究院有限公司 | 一种水溶性芳香族聚酰胺、制备方法及其电池隔膜 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2868770A (en) * | 1954-12-16 | 1959-01-13 | Ind Rayon Corp | Polyamides of para-aminophenyl aliphatic acids |
| US2894025A (en) * | 1955-09-07 | 1959-07-07 | Du Pont | Gamma-(3-aminocyclohexyl)butyric acid and esters |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB709924A (en) * | 1951-03-16 | 1954-06-02 | British Celanese | Improvements in the production of polyamides |
| US2831834A (en) * | 1951-05-12 | 1958-04-22 | Du Pont | Process for preparing polyamides |
| US3109836A (en) * | 1959-12-31 | 1963-11-05 | Exxon Research Engineering Co | Process for producing aromatic polyamides from acetamidobenzoic acids |
| US3079219A (en) * | 1960-12-06 | 1963-02-26 | Du Pont | Process for wet spinning aromatic polyamides |
-
0
- NL NL281227D patent/NL281227A/xx unknown
- BE BE620511D patent/BE620511A/xx unknown
-
1961
- 1961-10-18 US US146011A patent/US3203933A/en not_active Expired - Lifetime
-
1962
- 1962-07-17 GB GB27346/62A patent/GB963313A/en not_active Expired
- 1962-07-20 CH CH875062A patent/CH454457A/de unknown
- 1962-07-20 SE SE8104/62A patent/SE317199B/xx unknown
- 1962-07-20 DK DK325962AA patent/DK104375C/da active
- 1962-07-21 DE DEP1271A patent/DE1271985B/de active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2868770A (en) * | 1954-12-16 | 1959-01-13 | Ind Rayon Corp | Polyamides of para-aminophenyl aliphatic acids |
| US2894025A (en) * | 1955-09-07 | 1959-07-07 | Du Pont | Gamma-(3-aminocyclohexyl)butyric acid and esters |
Also Published As
| Publication number | Publication date |
|---|---|
| NL281227A (en, 2012) | |
| BE620511A (en, 2012) | |
| DK104375C (da) | 1966-05-09 |
| US3203933A (en) | 1965-08-31 |
| CH454457A (de) | 1968-04-15 |
| SE317199B (en, 2012) | 1969-11-10 |
| GB963313A (en) | 1964-07-08 |
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