CA1070447A - Aromatic copolyamides shaped articles therefrom and processes for producing said copolyamides and shaped articles - Google Patents
Aromatic copolyamides shaped articles therefrom and processes for producing said copolyamides and shaped articlesInfo
- Publication number
- CA1070447A CA1070447A CA242,585A CA242585A CA1070447A CA 1070447 A CA1070447 A CA 1070447A CA 242585 A CA242585 A CA 242585A CA 1070447 A CA1070447 A CA 1070447A
- Authority
- CA
- Canada
- Prior art keywords
- mole
- formula
- aromatic copolyamide
- group
- fibers
- 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
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims description 26
- 230000008569 process Effects 0.000 title claims description 5
- 150000004985 diamines Chemical class 0.000 claims abstract description 26
- 238000004519 manufacturing process Methods 0.000 claims abstract description 14
- 239000000243 solution Substances 0.000 claims description 79
- 229920000642 polymer Polymers 0.000 claims description 67
- 239000000835 fiber Substances 0.000 claims description 50
- -1 N-ethylpyrrolidone-2 Chemical compound 0.000 claims description 35
- 230000001112 coagulating effect Effects 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 22
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 20
- 239000001110 calcium chloride Substances 0.000 claims description 20
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 20
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 14
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000004760 aramid Substances 0.000 claims description 10
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 10
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- 229920003235 aromatic polyamide Polymers 0.000 claims description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 8
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 7
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 7
- 239000012433 hydrogen halide Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 125000004957 naphthylene group Chemical group 0.000 claims description 7
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 5
- 239000011592 zinc chloride Substances 0.000 claims description 5
- 235000005074 zinc chloride Nutrition 0.000 claims description 5
- LNWWQYYLZVZXKS-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanone Chemical compound CC(=O)N1CCCC1 LNWWQYYLZVZXKS-UHFFFAOYSA-N 0.000 claims description 4
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 claims description 4
- ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical compound [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 claims description 4
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 4
- MBHINSULENHCMF-UHFFFAOYSA-N n,n-dimethylpropanamide Chemical compound CCC(=O)N(C)C MBHINSULENHCMF-UHFFFAOYSA-N 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 4
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 claims description 4
- BNGXYYYYKUGPPF-UHFFFAOYSA-M (3-methylphenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].CC1=CC=CC(C[P+](C=2C=CC=CC=2)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 BNGXYYYYKUGPPF-UHFFFAOYSA-M 0.000 claims description 3
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 claims description 3
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 claims description 3
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 claims description 3
- 229910001507 metal halide Inorganic materials 0.000 claims description 3
- 150000005309 metal halides Chemical class 0.000 claims description 3
- GXMIHVHJTLPVKL-UHFFFAOYSA-N n,n,2-trimethylpropanamide Chemical compound CC(C)C(=O)N(C)C GXMIHVHJTLPVKL-UHFFFAOYSA-N 0.000 claims description 3
- AOXCXILUIVQCHH-UHFFFAOYSA-N n,n,n',n'-tetramethylpropanediamide Chemical compound CN(C)C(=O)CC(=O)N(C)C AOXCXILUIVQCHH-UHFFFAOYSA-N 0.000 claims description 3
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 claims description 3
- ZCOGQSHZVSZAHH-UHFFFAOYSA-N n,n-dimethylaziridine-1-carboxamide Chemical compound CN(C)C(=O)N1CC1 ZCOGQSHZVSZAHH-UHFFFAOYSA-N 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- 229910001631 strontium chloride Inorganic materials 0.000 claims description 3
- AHBGXTDRMVNFER-UHFFFAOYSA-L strontium dichloride Chemical compound [Cl-].[Cl-].[Sr+2] AHBGXTDRMVNFER-UHFFFAOYSA-L 0.000 claims description 3
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 claims description 3
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 claims description 2
- 229910001622 calcium bromide Inorganic materials 0.000 claims 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 claims 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 abstract description 25
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract description 21
- 239000002904 solvent Substances 0.000 abstract description 20
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 abstract description 18
- 229920001577 copolymer Polymers 0.000 abstract description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 4
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 39
- 208000012886 Vertigo Diseases 0.000 description 36
- 238000009987 spinning Methods 0.000 description 36
- 238000006116 polymerization reaction Methods 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 239000000178 monomer Substances 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
- 150000004984 aromatic diamines Chemical class 0.000 description 17
- 230000000379 polymerizing effect Effects 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 13
- 239000004952 Polyamide Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000001125 extrusion Methods 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- 239000000843 powder Substances 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 9
- 238000001035 drying Methods 0.000 description 8
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 229960000443 hydrochloric acid Drugs 0.000 description 7
- 235000011167 hydrochloric acid Nutrition 0.000 description 7
- 238000007493 shaping process Methods 0.000 description 7
- 238000005063 solubilization Methods 0.000 description 7
- 230000007928 solubilization Effects 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 6
- 239000011575 calcium Substances 0.000 description 5
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 5
- 239000000292 calcium oxide Substances 0.000 description 5
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 230000004580 weight loss Effects 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009740 moulding (composite fabrication) Methods 0.000 description 3
- 239000002798 polar solvent Substances 0.000 description 3
- 239000012779 reinforcing material Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000002166 wet spinning Methods 0.000 description 3
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- 238000012695 Interfacial polymerization Methods 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000002730 additional effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 230000008901 benefit Effects 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
- 239000004305 biphenyl Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 101100173790 Caulobacter vibrioides (strain ATCC 19089 / CB15) flbD gene Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001274660 Modulus Species 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 241000428533 Rhis Species 0.000 description 1
- 241000592503 Speea Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QNHKJSKLKSGFJF-UHFFFAOYSA-N [Br].[Ca] Chemical compound [Br].[Ca] QNHKJSKLKSGFJF-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 229940000425 combination drug Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000000578 dry spinning Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 101150064711 fliO gene Proteins 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 125000005067 haloformyl group Chemical group 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012210 heat-resistant fiber Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229940047889 isobutyramide Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003366 poly(p-phenylene terephthalamide) Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- C08G69/26—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids
- C08G69/32—Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids derived from polyamines and polycarboxylic acids from aromatic diamines and aromatic dicarboxylic acids with both amino and carboxylic groups aromatically bound
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/80—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyamides
- D01F6/805—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyamides from aromatic copolyamides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Polyamides (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14902774A JPS5176386A (ja) | 1974-12-27 | 1974-12-27 | Hokozokuhoriamidonoseizoho |
| JP5920075A JPS51134743A (en) | 1975-05-20 | 1975-05-20 | Aromatic polyamide solution |
| JP5920175A JPS51136916A (en) | 1975-05-20 | 1975-05-20 | Aromatic polyamide fibers and method of manuf acturing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1070447A true CA1070447A (en) | 1980-01-22 |
Family
ID=27296804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA242,585A Expired CA1070447A (en) | 1974-12-27 | 1975-12-24 | Aromatic copolyamides shaped articles therefrom and processes for producing said copolyamides and shaped articles |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4075172A (OSRAM) |
| AU (1) | AU500143B2 (OSRAM) |
| BR (1) | BR7508668A (OSRAM) |
| CA (1) | CA1070447A (OSRAM) |
| DE (1) | DE2556883C2 (OSRAM) |
| ES (1) | ES443888A1 (OSRAM) |
| FR (1) | FR2295977A1 (OSRAM) |
| GB (1) | GB1501948A (OSRAM) |
| IT (1) | IT1051943B (OSRAM) |
| NL (1) | NL175830C (OSRAM) |
| NZ (1) | NZ179586A (OSRAM) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL157327C (nl) * | 1975-02-21 | 1984-05-16 | Akzo Nv | Werkwijze ter bereiding van poly-p-fenyleentereftaalamide. |
| DE2554932A1 (de) * | 1975-12-06 | 1977-06-08 | Bayer Ag | Semipermeable membranen aus copolyamiden |
| US4162346A (en) * | 1976-09-23 | 1979-07-24 | Celanese Corporation | High performance wholly aromatic polyamide fibers |
| FR2388844A1 (fr) * | 1977-04-27 | 1978-11-24 | Rhone Poulenc Textile | Procede d'obtention en discontinu de polymeres derives de para-phenylenediamine |
| US4297479A (en) * | 1977-04-27 | 1981-10-27 | Rhone-Poulenc-Textile | Process for the continuous production of aromatic polyamides in a mixture of calcium chloride and N-methylpyrrolidone-2 |
| US4245082A (en) * | 1979-07-09 | 1981-01-13 | E. I. Du Pont De Nemours And Company | Polyesters derived from 3,4'-dihydroxy-benzophenones or 3-hydroxy-4'-(4-hydroxyphenyl-)benzophenone and certain aromatic dicarboxylic acids and filaments thereof |
| JPS55115428A (en) * | 1979-02-26 | 1980-09-05 | Teijin Ltd | Aromatic compolyamide and preparation thereof |
| JPS56107073A (en) * | 1980-01-22 | 1981-08-25 | Teijin Ltd | Improved all aromatic polyamide fiber and cloth |
| JPS5734125A (en) * | 1980-08-07 | 1982-02-24 | Teijin Ltd | Fully aromatic polyamide fiber and film and their production |
| US4532275A (en) * | 1981-02-03 | 1985-07-30 | Teijin Limited | Fiber-reinforced composite materials |
| JPS60231873A (ja) * | 1984-04-26 | 1985-11-18 | 帝人株式会社 | 全芳香族ポリアミド繊維 |
| DE3674620D1 (de) * | 1985-03-23 | 1990-11-08 | Hoechst Ag | Geformte gebilde aus aromatischen copolyamiden und verfahren zu ihrer herstellung. |
| JPS62116303A (ja) * | 1985-11-18 | 1987-05-27 | Bridgestone Corp | 重車両用空気入りタイヤ |
| US4914180A (en) * | 1988-09-30 | 1990-04-03 | Hoechst Celanese Corporation | Polyamides prepared from 2-(3-aminophenyl)-2-(4-aminophenyl) hexafluoro propane |
| US4952669A (en) * | 1988-09-30 | 1990-08-28 | Hoechst Celanese Corp. | Copolyimides prepared from 2-(3-aminophenyl)-2-(4-aminophenyl) Hexafluoro propane |
| US4978742A (en) * | 1988-09-30 | 1990-12-18 | Hoechst Celanese Corp. | Polymers prepared from 2-(3-aminophenyl)-2-(4-aminophenyl) hexafluoro propane |
| DE3835419A1 (de) * | 1988-10-18 | 1990-04-19 | 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 |
| DE3835405A1 (de) * | 1988-10-18 | 1990-05-03 | Hoechst Ag | Vollaromatische polyamide, verfahren zu ihrer herstellung und daraus geformte gebilde |
| US4869947A (en) * | 1988-12-21 | 1989-09-26 | E. I. Du Pont De Nemours And Company | Laminated fabric for protective clothing |
| US4980446A (en) * | 1989-03-16 | 1990-12-25 | E. I. Du Pont De Nemours And Company | Melt-processible aromatic containing copolyamide from 3,4'-bis (amino phenyl)ether |
| JPH03143922A (ja) * | 1989-10-30 | 1991-06-19 | Teijin Ltd | 全芳香族共重合ポリアミド及びその成形物 |
| DE4007142A1 (de) * | 1990-03-07 | 1991-09-12 | Hoechst Ag | Aromatische copolyamide, verfahren zu ihrer herstellung und daraus geformte gebilde |
| DE4138872B4 (de) * | 1990-03-30 | 2005-12-29 | E.I. Du Pont De Nemours And Co., Wilmington | Verstreckbare Aramide hoher Zugfestigkeit |
| US5459231A (en) * | 1990-03-30 | 1995-10-17 | E. I. Du Pont De Nemours And Company | Drawable high tensile strength aramids |
| US5266672A (en) * | 1991-07-02 | 1993-11-30 | Hoechst Aktiengesellschaft | Aromatic copolyaide from diamino benzanilide |
| JPH05163610A (ja) * | 1991-12-18 | 1993-06-29 | Teijin Ltd | 芳香族ポリアミド偏平繊維 |
| US5334694A (en) * | 1992-01-27 | 1994-08-02 | Hoechst Aktiengesellschaft | Aromatic copolyamides, processes for their preparation and structures formed therefrom |
| DE69305913T2 (de) * | 1992-05-07 | 1997-05-07 | Teijin Ltd | Aromatische Polyamidfäden mit verbesserter Wetterwiderstandsfähigkeit |
| DE4421650A1 (de) | 1994-06-21 | 1996-01-04 | Hoechst Ag | Formkörper enthaltend Garne oder Bänder aus Fasern aus aromatischen Polyamiden, Garne oder Bänder aus aromatischen Polyamiden, sowie Verwendung dieser Garne zur Verstärkung von Polymerbeton oder von hydraulisch oder an der Luft abbindenden Materialien |
| DE4443456A1 (de) | 1994-12-07 | 1996-07-04 | Hoechst Trevira Gmbh & Co Kg | Zweikomponenten-Schlingengarne aus Aramidfilamenten, Verfahren zu deren Herstellung und deren Verwendung |
| DE19605511A1 (de) | 1996-02-15 | 1997-08-21 | Hoechst Trevira Gmbh & Co Kg | Schnittresistente Aramidfasern, Garne enthaltend diese Aramidfasern und deren Verwendung |
| DE19606959A1 (de) | 1996-02-26 | 1997-09-04 | Hoechst Trevira Gmbh & Co Kg | Faserpulp, Verfahren zu dessen Herstellung und dessen Verwendung |
| JP3142777B2 (ja) * | 1996-05-22 | 2001-03-07 | 帝人株式会社 | 芳香族ポリアミド剛毛 |
| KR100448034B1 (ko) * | 1997-05-20 | 2005-06-01 | 데이진 가부시키가이샤 | 이축배향적층전방향족폴리아미드막및자기기록매체 |
| EP0913421B1 (en) | 1997-10-27 | 2003-03-26 | Teijin Limited | Biaxially oriented film and magnetic recording medium comprising the same as a base film |
| EP1003156A4 (en) | 1998-04-13 | 2000-05-24 | Teijin Ltd | AROMATIC POLYAMIDE LAYER FOR HIGH DENSITY MAGNETIC RECORDING |
| JP3475234B2 (ja) * | 1998-10-15 | 2003-12-08 | 帝人テクノプロダクツ株式会社 | 芳香族ポリアミド繊維紙 |
| EP0994215B1 (en) * | 1998-10-15 | 2003-06-04 | Teijin Limited | Wholly aromatic polyamide fiber synthetic paper sheet |
| CN100368461C (zh) * | 2003-03-05 | 2008-02-13 | 东丽株式会社 | 芳香族高分子、膜、电解质膜和隔板 |
| US8118975B2 (en) * | 2007-12-21 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Papers containing fibrids derived from diamino diphenyl sulfone |
| US8114251B2 (en) * | 2007-12-21 | 2012-02-14 | E.I. Du Pont De Nemours And Company | Papers containing fibrids derived from diamino diphenyl sulfone |
| US7803247B2 (en) * | 2007-12-21 | 2010-09-28 | E.I. Du Pont De Nemours And Company | Papers containing floc derived from diamino diphenyl sulfone |
| CN103314144B (zh) * | 2011-01-13 | 2015-08-19 | 纳幕尔杜邦公司 | 共聚物纤维的制备和干燥 |
| DE102011003958A1 (de) | 2011-02-10 | 2012-08-16 | Papierfabrik Schoellershammer Heinr. Aug. Schoeller Söhne GmbH & Co. KG | Zellstoffbasierte hitzebeständige Papiere mit hoher Durchschlagsfestigkeit und Verfahren zur Herstellung derselben |
| EP3026148B1 (en) * | 2014-11-27 | 2019-02-13 | Teijin Limited | Cord comprising a fully aromatic polyamide fiber |
| RU2659975C1 (ru) * | 2017-09-07 | 2018-07-04 | Тамара Курмангазиевна Мусина | Нить на основе ароматического гетероциклического сополиамида с улучшенными эластическими свойствами и способ ее получения |
| CN114053890B (zh) * | 2021-12-09 | 2023-07-18 | 天津工业大学 | 一种高性能耐碱纳滤膜及其制备方法 |
| CN118047945B (zh) * | 2024-04-16 | 2024-06-25 | 烟台泰和新材高分子新材料研究院有限公司 | 一种高粘度芳香族聚酰胺共聚原液及制备方法和应用 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL108288C (OSRAM) * | 1957-02-28 | |||
| BE565268A (OSRAM) * | 1957-02-28 | |||
| US3322728A (en) * | 1963-06-17 | 1967-05-30 | Du Pont | Sulfonyl aromatic polyamides |
| US3354125A (en) * | 1963-07-29 | 1967-11-21 | Monsanto Co | Polymers from diaminobenzanilides |
| NL133092C (OSRAM) * | 1965-05-21 | |||
| US3354127A (en) * | 1966-04-18 | 1967-11-21 | Du Pont | Aromatic copolyamides |
| DE1720984A1 (de) * | 1966-08-03 | 1971-07-22 | Ici Ltd | Polyamide und Verfahren zu deren Herstellung |
| DE1595681A1 (de) * | 1966-09-19 | 1970-01-22 | Bayer Ag | Verfahren zur Herstellung von hochschmelzenden Polyamiden |
| US3498955A (en) * | 1967-07-06 | 1970-03-03 | Monsanto Co | Neutralization of polymerization solutions of aromatic polyamides |
| GB1201531A (en) * | 1968-01-24 | 1970-08-05 | Ici Ltd | Aromatic polyamides |
| GB1254005A (en) * | 1969-05-02 | 1971-11-17 | Ici Ltd | Copolyamides and their production |
| DE2037254A1 (de) * | 1970-07-28 | 1972-02-03 | Farbwerke Hoechst AG, vorm. Meister Lucius & Brüning, 6000 Frankfurt | Verfahren zur Herstellung von Fäden aus hochschmelzenden Polyamiden |
| CH545861A (OSRAM) * | 1971-02-11 | 1974-02-15 | ||
| US3738964A (en) * | 1972-05-31 | 1973-06-12 | Monsanto Co | Aromatic polyamides derived from a mixture of aromatic diamines containing 4,4-diamino-oxanilide |
| DE2248663A1 (de) * | 1972-10-04 | 1974-04-11 | Bayer Ag | Aromatische copolyamide und daraus hergestellte faeden mit hohem elastizitaetsmodul und hoher reissfestigkeit |
| DE2259123A1 (de) * | 1972-12-02 | 1974-06-06 | Bayer Ag | Chinazolindion-strukturen enthaltende copolyamide |
| JPS5523923B2 (OSRAM) * | 1973-02-01 | 1980-06-26 | ||
| JPS49130494A (OSRAM) * | 1973-04-17 | 1974-12-13 |
-
1975
- 1975-12-17 DE DE2556883A patent/DE2556883C2/de not_active Expired
- 1975-12-17 AU AU87626/75A patent/AU500143B2/en not_active Expired
- 1975-12-18 GB GB51844/75A patent/GB1501948A/en not_active Expired
- 1975-12-18 US US05/641,898 patent/US4075172A/en not_active Expired - Lifetime
- 1975-12-18 NZ NZ179586A patent/NZ179586A/xx unknown
- 1975-12-23 IT IT30748/75A patent/IT1051943B/it active
- 1975-12-24 CA CA242,585A patent/CA1070447A/en not_active Expired
- 1975-12-26 BR BR7508668*A patent/BR7508668A/pt unknown
- 1975-12-26 ES ES75443888A patent/ES443888A1/es not_active Expired
- 1975-12-26 FR FR7539827A patent/FR2295977A1/fr active Granted
- 1975-12-29 NL NLAANVRAGE7515131,A patent/NL175830C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2556883C2 (de) | 1981-11-26 |
| BR7508668A (pt) | 1976-09-08 |
| NZ179586A (en) | 1978-04-03 |
| AU500143B2 (en) | 1979-05-10 |
| FR2295977A1 (fr) | 1976-07-23 |
| NL7515131A (nl) | 1976-06-29 |
| NL175830C (nl) | 1985-01-02 |
| GB1501948A (en) | 1978-02-22 |
| ES443888A1 (es) | 1977-05-01 |
| DE2556883A1 (de) | 1976-07-01 |
| IT1051943B (it) | 1981-05-20 |
| AU8762675A (en) | 1977-06-23 |
| FR2295977B1 (OSRAM) | 1979-06-22 |
| US4075172A (en) | 1978-02-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |