DE1810426B2 - Aromatische Polyamide enthaltende, optisch anisotrope Masse - Google Patents
Aromatische Polyamide enthaltende, optisch anisotrope MasseInfo
- Publication number
- DE1810426B2 DE1810426B2 DE1810426A DE1810426A DE1810426B2 DE 1810426 B2 DE1810426 B2 DE 1810426B2 DE 1810426 A DE1810426 A DE 1810426A DE 1810426 A DE1810426 A DE 1810426A DE 1810426 B2 DE1810426 B2 DE 1810426B2
- Authority
- DE
- Germany
- Prior art keywords
- mass
- polyamide
- filaments
- water
- anisotropic
- 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.)
- Withdrawn
Links
- 239000004760 aramid Substances 0.000 title description 6
- 229920003235 aromatic polyamide Polymers 0.000 title description 6
- 229920002647 polyamide Polymers 0.000 claims description 364
- 239000004952 Polyamide Substances 0.000 claims description 363
- 239000000203 mixture Substances 0.000 claims description 227
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 173
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 78
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 51
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 33
- 239000001110 calcium chloride Substances 0.000 claims description 33
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 33
- 150000001408 amides Chemical group 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 10
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims description 7
- KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 5
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 claims description 5
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 claims description 2
- YLHUPYSUKYAIBW-UHFFFAOYSA-N 1-acetylpyrrolidin-2-one Chemical compound CC(=O)N1CCCC1=O YLHUPYSUKYAIBW-UHFFFAOYSA-N 0.000 claims 1
- 150000008430 aromatic amides Chemical group 0.000 claims 1
- 125000002837 carbocyclic group Chemical group 0.000 claims 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 claims 1
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 claims 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 268
- 238000003756 stirring Methods 0.000 description 126
- 238000001035 drying Methods 0.000 description 119
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 113
- 238000004519 manufacturing process Methods 0.000 description 106
- 239000000243 solution Substances 0.000 description 105
- 238000009987 spinning Methods 0.000 description 83
- 238000002360 preparation method Methods 0.000 description 76
- 238000010438 heat treatment Methods 0.000 description 67
- 239000000463 material Substances 0.000 description 62
- 229920003190 poly( p-benzamide) Polymers 0.000 description 55
- 229910052757 nitrogen Inorganic materials 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 50
- 238000001816 cooling Methods 0.000 description 48
- 239000007787 solid Substances 0.000 description 47
- 239000011521 glass Substances 0.000 description 46
- 238000000034 method Methods 0.000 description 42
- 238000002166 wet spinning Methods 0.000 description 40
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 37
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical group ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 35
- 239000005457 ice water Substances 0.000 description 34
- 150000003839 salts Chemical class 0.000 description 32
- 239000000523 sample Substances 0.000 description 32
- 239000002808 molecular sieve Substances 0.000 description 31
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000000835 fiber Substances 0.000 description 30
- 229910001220 stainless steel Inorganic materials 0.000 description 30
- 239000010935 stainless steel Substances 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 29
- -1 p-aminobenzoyl halide salts Chemical class 0.000 description 28
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 26
- VSCADKGMBQAGNC-UHFFFAOYSA-N 4-aminobenzoyl chloride;hydrochloride Chemical compound Cl.NC1=CC=C(C(Cl)=O)C=C1 VSCADKGMBQAGNC-UHFFFAOYSA-N 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 24
- 239000000499 gel Substances 0.000 description 24
- 238000002156 mixing Methods 0.000 description 24
- 238000010586 diagram Methods 0.000 description 23
- 238000001914 filtration Methods 0.000 description 21
- 238000005406 washing Methods 0.000 description 21
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 20
- 239000012530 fluid Substances 0.000 description 20
- 239000002253 acid Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 18
- 101100219382 Caenorhabditis elegans cah-2 gene Proteins 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- 235000013877 carbamide Nutrition 0.000 description 16
- 150000004985 diamines Chemical class 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 15
- 239000007789 gas Substances 0.000 description 14
- 238000002347 injection Methods 0.000 description 13
- 239000007924 injection Substances 0.000 description 13
- 239000002245 particle Substances 0.000 description 13
- 239000002244 precipitate Substances 0.000 description 13
- 239000004698 Polyethylene Substances 0.000 description 12
- 239000004202 carbamide Substances 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- 238000006068 polycondensation reaction Methods 0.000 description 12
- 229920000573 polyethylene Polymers 0.000 description 12
- 238000011282 treatment Methods 0.000 description 12
- FZXVVMPYCPCKGU-UHFFFAOYSA-N 4-(3-chloro-7-azabicyclo[2.2.1]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=C1C=C2Cl FZXVVMPYCPCKGU-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000001556 precipitation Methods 0.000 description 11
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 11
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 10
- 230000002378 acidificating effect Effects 0.000 description 10
- 239000001569 carbon dioxide Substances 0.000 description 10
- 229910002092 carbon dioxide Inorganic materials 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 229910001203 Alloy 20 Inorganic materials 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
- 238000007792 addition Methods 0.000 description 8
- 239000012153 distilled water Substances 0.000 description 8
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 8
- 229910052808 lithium carbonate Inorganic materials 0.000 description 8
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 7
- QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011888 foil Substances 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 230000028161 membrane depolarization Effects 0.000 description 7
- 230000003472 neutralizing effect Effects 0.000 description 7
- 229910000510 noble metal Inorganic materials 0.000 description 7
- 238000010587 phase diagram Methods 0.000 description 7
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 7
- 239000004810 polytetrafluoroethylene Substances 0.000 description 7
- 239000010970 precious metal Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000008859 change Effects 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000007654 immersion Methods 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 238000002791 soaking Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000000007 visual effect Effects 0.000 description 6
- 238000004804 winding Methods 0.000 description 6
- 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 5
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 5
- 238000012935 Averaging Methods 0.000 description 5
- 229960004050 aminobenzoic acid Drugs 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229910001873 dinitrogen Inorganic materials 0.000 description 5
- 238000000578 dry spinning Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 230000010494 opalescence Effects 0.000 description 5
- 230000035699 permeability Effects 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000011343 solid material Substances 0.000 description 5
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 230000009471 action Effects 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 238000011065 in-situ storage Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 230000010287 polarization Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 3
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 description 3
- WRDNCFQZLUCIRH-UHFFFAOYSA-N 4-(7-azabicyclo[2.2.1]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=C1C=C2 WRDNCFQZLUCIRH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 238000000498 ball milling Methods 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000015271 coagulation Effects 0.000 description 3
- 238000005345 coagulation Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 3
- 229910001947 lithium oxide Inorganic materials 0.000 description 3
- 229940018564 m-phenylenediamine Drugs 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
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- 238000004062 sedimentation Methods 0.000 description 3
- 238000004513 sizing Methods 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HQCHAOKWWKLXQH-UHFFFAOYSA-N 2,6-Dichloro-para-phenylenediamine Chemical compound NC1=CC(Cl)=C(N)C(Cl)=C1 HQCHAOKWWKLXQH-UHFFFAOYSA-N 0.000 description 2
- LOBHYTSONQJQIO-UHFFFAOYSA-N 4-(4-aminophenyl)benzoyl chloride;hydrochloride Chemical compound Cl.C1=CC(N)=CC=C1C1=CC=C(C(Cl)=O)C=C1 LOBHYTSONQJQIO-UHFFFAOYSA-N 0.000 description 2
- BWQMFPUGRMIGCL-UHFFFAOYSA-N 4-aminobenzoyl chloride;sulfuric acid Chemical compound OS(O)(=O)=O.NC1=CC=C(C(Cl)=O)C=C1 BWQMFPUGRMIGCL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- NKDPEERISRRYSY-UHFFFAOYSA-M [Cl-].[Li+].CN(C(N(C)C)=O)C Chemical compound [Cl-].[Li+].CN(C(N(C)C)=O)C NKDPEERISRRYSY-UHFFFAOYSA-M 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 238000005219 brazing Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000011088 calibration curve Methods 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 230000001112 coagulating effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 150000003950 cyclic amides Chemical class 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000002999 depolarising effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000007429 general method Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
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- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
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- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- VQUHVWVGRKTIBH-UHFFFAOYSA-N hydron;2-methylbenzene-1,4-diamine;dichloride Chemical compound Cl.Cl.CC1=CC(N)=CC=C1N VQUHVWVGRKTIBH-UHFFFAOYSA-N 0.000 description 1
- JEGUKCSWCFPDGT-UHFFFAOYSA-M hydroxide;hydrate Chemical compound O.[OH-] JEGUKCSWCFPDGT-UHFFFAOYSA-M 0.000 description 1
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- 150000002513 isocyanates Chemical class 0.000 description 1
- QZUPTXGVPYNUIT-UHFFFAOYSA-N isophthalamide Chemical compound NC(=O)C1=CC=CC(C(N)=O)=C1 QZUPTXGVPYNUIT-UHFFFAOYSA-N 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
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- VIJUZNJJLALGNJ-UHFFFAOYSA-N n,n-dimethylbutanamide Chemical compound CCCC(=O)N(C)C VIJUZNJJLALGNJ-UHFFFAOYSA-N 0.000 description 1
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- 108010089741 opacity factor Proteins 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Artificial Filaments (AREA)
- Polyamides (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Adhesive Tapes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73641068A | 1968-06-12 | 1968-06-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1810426A1 DE1810426A1 (de) | 1970-02-12 |
| DE1810426B2 true DE1810426B2 (de) | 1980-08-28 |
Family
ID=24959750
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1810426A Withdrawn DE1810426B2 (de) | 1968-06-12 | 1968-11-22 | Aromatische Polyamide enthaltende, optisch anisotrope Masse |
| DE1929713A Withdrawn DE1929713B2 (de) | 1968-06-12 | 1969-06-11 | Anisotrope Massen |
| DE19691929694 Withdrawn DE1929694B2 (de) | 1968-06-12 | 1969-06-11 | Optisch anisotrope massen von aromatischen polyamiden |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1929713A Withdrawn DE1929713B2 (de) | 1968-06-12 | 1969-06-11 | Anisotrope Massen |
| DE19691929694 Withdrawn DE1929694B2 (de) | 1968-06-12 | 1969-06-11 | Optisch anisotrope massen von aromatischen polyamiden |
Country Status (10)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1929694A1 (de) * | 1968-06-12 | 1970-09-03 | Du Pont | Masse und daraus hergestellte Gegenstaende |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL39187A (en) * | 1971-04-28 | 1976-02-29 | Du Pont | Polyamide fibers and films and their preparation |
| TR18539A (tr) * | 1971-04-28 | 1977-03-16 | Du Pont | Ueruen ve usul |
| IL39188A (en) * | 1971-04-28 | 1976-02-29 | Du Pont | Poly(p-phenylene terephthalamide)fibers and their preparation |
| SE416814B (sv) * | 1974-05-10 | 1981-02-09 | Du Pont | Nya syntetiska polyestrar och sett for deras framstellning |
| NL157327C (nl) * | 1975-02-21 | 1984-05-16 | Akzo Nv | Werkwijze ter bereiding van poly-p-fenyleentereftaalamide. |
| JPS52160040U (enrdf_load_stackoverflow) * | 1976-05-27 | 1977-12-05 | ||
| JPS5335351U (enrdf_load_stackoverflow) * | 1976-08-31 | 1978-03-28 | ||
| JPS55122011A (en) * | 1979-03-13 | 1980-09-19 | Asahi Chem Ind Co Ltd | Poly-p-phenylene terephthalamide fiber having high young's modulus and its preparation |
| JPS55122012A (en) * | 1979-03-13 | 1980-09-19 | Asahi Chem Ind Co Ltd | Poly-p-phenylene terephthalamide fiber having improved fatigue resistance and its production |
| NL8601159A (nl) * | 1986-05-06 | 1987-12-01 | Akzo Nv | Vezels en garens uit een mengsel van aromatische polyamiden. |
| DE3835405A1 (de) * | 1988-10-18 | 1990-05-03 | Hoechst Ag | Vollaromatische polyamide, verfahren zu ihrer herstellung und daraus geformte gebilde |
| DE3835441A1 (de) * | 1988-10-18 | 1990-04-26 | Hoechst Ag | Vollaromatische polyamide, verfahren zu ihrer herstellung und daraus geformte gebilde |
| DE4128401C2 (de) * | 1991-08-23 | 1995-07-20 | Lucht Elektro Flaechen Teil Sp | Heizkassette |
| TW226417B (enrdf_load_stackoverflow) * | 1992-05-28 | 1994-07-11 | Sumitomo Chemical Co | |
| AU2004236347B2 (en) * | 2003-05-08 | 2009-03-05 | Teijin Aramid B.V. | Non-fibrous polymer solution of para-aramid with high relative viscosity |
| JP2008150577A (ja) * | 2006-11-22 | 2008-07-03 | Teijin Ltd | 光学異方性ドープおよびその製造方法 |
| JP6004763B2 (ja) * | 2011-06-22 | 2016-10-12 | 帝人株式会社 | 全芳香族ポリアミド溶液の製造方法 |
| KR101386429B1 (ko) * | 2012-12-28 | 2014-04-29 | 코오롱인더스트리 주식회사 | 파라-아라미드 섬유의 제조방법 |
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| US556934A (en) * | 1896-03-24 | Sectional chute for coal-wagons | ||
| NL272131A (enrdf_load_stackoverflow) * | 1900-01-01 | |||
| US693739A (en) * | 1901-12-06 | 1902-02-18 | Louis B Prahar | Chatelaine-hook. |
| US736410A (en) * | 1902-09-12 | 1903-08-18 | Miles J Lawler | Washing-machine. |
| US729158A (en) * | 1903-02-14 | 1903-05-26 | Cyrus A Haas | Gas arc-lamp. |
| DE1745254U (de) | 1956-09-12 | 1957-05-23 | Philips Patentverwaltung | Hohlraumverschluss. |
| US3063966A (en) * | 1958-02-05 | 1962-11-13 | Du Pont | Process of making wholly aromatic polyamides |
| BE565268A (enrdf_load_stackoverflow) * | 1957-02-28 | |||
| NL108288C (enrdf_load_stackoverflow) * | 1957-02-28 | |||
| BE565269A (enrdf_load_stackoverflow) * | 1957-03-27 | |||
| US3094511A (en) | 1958-11-17 | 1963-06-18 | Du Pont | Wholly aromatic polyamides |
| DE1810425U (de) | 1960-01-09 | 1960-04-28 | Helmut Strobel | Legeschiene fuer wirkmaschinen, insbesondere raschelmaschinen. |
| DE1810426U (de) | 1960-01-15 | 1960-04-28 | Tuellmaschb Karl Marx Stadt Ve | Kettenfadenwaechter fuer wirkmaschinen, vielnadelnaehmaschinen, webstuehle u. dgl. |
| DE1816106U (de) | 1960-02-17 | 1960-08-04 | Fritz Schwarzer | Registriersystem. |
| BE600587A (enrdf_load_stackoverflow) * | 1960-02-25 | |||
| NL132625C (enrdf_load_stackoverflow) | 1960-05-31 | |||
| GB931678A (en) * | 1961-05-09 | 1963-07-17 | Courtaulds Ltd | Improvements in and relating to the production of artificial threads of poly-gamma-methyl glutamate |
| US3154610A (en) | 1961-05-31 | 1964-10-27 | Celanese Corp | Process of wet spinning polyamides and prevention of gel formation |
| NL290764A (enrdf_load_stackoverflow) * | 1962-03-29 | |||
| BE630312A (enrdf_load_stackoverflow) | 1962-03-29 | |||
| US3154613A (en) * | 1962-03-29 | 1964-10-27 | Celanese Corp | Spinning filaments from solutions in concentrated sulfuric acid of a polyamide and salt |
| BE637257A (enrdf_load_stackoverflow) * | 1962-09-11 | |||
| NL297736A (enrdf_load_stackoverflow) | 1962-09-11 | |||
| US3354125A (en) * | 1963-07-29 | 1967-11-21 | Monsanto Co | Polymers from diaminobenzanilides |
| US3414645A (en) | 1964-06-19 | 1968-12-03 | Monsanto Co | Process for spinning wholly aromatic polyamide fibers |
| US3322824A (en) * | 1964-07-02 | 1967-05-30 | Celanese Corp | Compositions containing a polytereph-thalamide and a hydrocarbon-substituted sulfonicacid, and process utilizing the same in making shaped articles |
| FR1482822A (fr) * | 1965-06-19 | 1967-06-02 | Monsanto Co | Procédé pour le filage de fibres résistant à la chaleur et produits obtenus à l'aide de ce procédé |
| DE1929713U (de) | 1965-10-01 | 1965-12-23 | Herbert Ernst | Statisch tragende platte. |
| US3671542A (en) | 1966-06-13 | 1972-06-20 | Du Pont | Optically anisotropic aromatic polyamide dopes |
| DE1745254A1 (de) * | 1966-06-13 | 1970-12-23 | Du Pont | Polyamidfaeden,-fasern,-folien und -fibriden |
| US3349062A (en) * | 1966-07-21 | 1967-10-24 | Du Pont | Halogenated aromatic polyamides |
| CA928440A (en) * | 1967-12-27 | 1973-06-12 | I. Bair Thomas | Fibres of aromatic para-oriented polyterephthalamides |
| US3817941A (en) * | 1967-12-27 | 1974-06-18 | Du Pont | Wholly aromatic carbocyclic poly-carbonamide fiber having initial modulus in excess of 170 gpd and orientation angle of up to 40 grad |
| FR2008569A1 (enrdf_load_stackoverflow) * | 1968-05-15 | 1970-01-23 | Du Pont | |
| DE1810426B2 (de) * | 1968-06-12 | 1980-08-28 | E.I. Du Pont De Nemours And Co., Wilmington, Del. (V.St.A.) | Aromatische Polyamide enthaltende, optisch anisotrope Masse |
| DE1816906A1 (de) * | 1968-12-24 | 1970-07-02 | Stauffer Chemical Co | Verfahren zur Herstellung von schwefelfreiem Chlorwasserstoff |
| US3819587A (en) * | 1969-05-23 | 1974-06-25 | Du Pont | Wholly aromatic carbocyclic polycarbonamide fiber having orientation angle of less than about 45{20 |
| US3673143A (en) | 1970-06-24 | 1972-06-27 | Du Pont | Optically anisotropic spinning dopes of polycarbonamides |
| IL39187A (en) * | 1971-04-28 | 1976-02-29 | Du Pont | Polyamide fibers and films and their preparation |
| JPS5013365A (enrdf_load_stackoverflow) * | 1973-06-11 | 1975-02-12 | ||
| FR2230885B1 (enrdf_load_stackoverflow) * | 1973-04-13 | 1977-07-29 | Precision Industrielle | |
| DE2412458A1 (de) * | 1973-04-19 | 1974-11-07 | Rudolf Felix Dipl In Homberger | Vorrichtung mit mindestens einer druckmedium betaetigbaren einheit |
| JPS5012006A (enrdf_load_stackoverflow) * | 1973-05-31 | 1975-02-07 | ||
| JPS558697B2 (enrdf_load_stackoverflow) * | 1973-06-04 | 1980-03-05 |
-
1968
- 1968-11-22 DE DE1810426A patent/DE1810426B2/de not_active Withdrawn
- 1968-11-22 JP JP43085534A patent/JPS5012006B1/ja active Pending
-
1969
- 1969-06-09 ES ES368172A patent/ES368172A1/es not_active Expired
- 1969-06-10 LU LU58840D patent/LU58840A1/xx unknown
- 1969-06-11 DE DE1929713A patent/DE1929713B2/de not_active Withdrawn
- 1969-06-11 BR BR209669/69A patent/BR6909669D0/pt unknown
- 1969-06-11 DE DE19691929694 patent/DE1929694B2/de not_active Withdrawn
- 1969-06-11 JP JP44045474A patent/JPS508474B1/ja active Pending
- 1969-06-11 FR FR6919392A patent/FR2010753A1/fr active Pending
- 1969-06-11 BE BE734387D patent/BE734387A/xx not_active IP Right Cessation
- 1969-06-12 GB GB29772/69A patent/GB1283064A/en not_active Expired
- 1969-06-12 NL NL6908984A patent/NL6908984A/xx unknown
- 1969-06-12 CH CH901169A patent/CH487212A/de not_active IP Right Cessation
- 1969-06-12 NL NL696908989A patent/NL148348B/xx not_active Application Discontinuation
-
1972
- 1972-11-25 JP JP47117718A patent/JPS5013365B1/ja active Pending
-
1974
- 1974-12-26 JP JP49148543A patent/JPS5035941B1/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1929694A1 (de) * | 1968-06-12 | 1970-09-03 | Du Pont | Masse und daraus hergestellte Gegenstaende |
Also Published As
| Publication number | Publication date |
|---|---|
| ES368172A1 (es) | 1972-04-01 |
| JPS508474B1 (enrdf_load_stackoverflow) | 1975-04-04 |
| JPS5013365B1 (enrdf_load_stackoverflow) | 1975-05-19 |
| FR2010753A1 (enrdf_load_stackoverflow) | 1970-02-20 |
| DE1929713A1 (de) | 1970-02-12 |
| NL6908984A (enrdf_load_stackoverflow) | 1969-12-16 |
| BR6909669D0 (pt) | 1973-01-16 |
| NL148348B (nl) | 1976-01-15 |
| BE734387A (enrdf_load_stackoverflow) | 1969-12-11 |
| LU58840A1 (enrdf_load_stackoverflow) | 1969-10-30 |
| CH487212A (de) | 1970-03-15 |
| DE1929713B2 (de) | 1975-07-03 |
| NL6908989A (enrdf_load_stackoverflow) | 1969-12-16 |
| JPS5012006B1 (enrdf_load_stackoverflow) | 1975-05-08 |
| DE1810426A1 (de) | 1970-02-12 |
| DE1929694A1 (de) | 1970-09-03 |
| JPS5035941B1 (enrdf_load_stackoverflow) | 1975-11-20 |
| DE1929694B2 (de) | 1976-04-22 |
| GB1283064A (en) | 1972-07-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8230 | Patent withdrawn |