DE2257706A1 - Verfahren zur herstellung aromatischer oxadiazol/n-alkylhydrazid-polymerisate - Google Patents
Verfahren zur herstellung aromatischer oxadiazol/n-alkylhydrazid-polymerisateInfo
- Publication number
- DE2257706A1 DE2257706A1 DE19722257706 DE2257706A DE2257706A1 DE 2257706 A1 DE2257706 A1 DE 2257706A1 DE 19722257706 DE19722257706 DE 19722257706 DE 2257706 A DE2257706 A DE 2257706A DE 2257706 A1 DE2257706 A1 DE 2257706A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- reactants
- sulfuric acid
- solution
- molar ratio
- 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 42
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 48
- 239000000243 solution Substances 0.000 claims description 41
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 claims description 38
- 239000000376 reactant Substances 0.000 claims description 34
- 229920000642 polymer Polymers 0.000 claims description 27
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 24
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 24
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 16
- 239000000835 fiber Substances 0.000 claims description 15
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 15
- FUSNOPLQVRUIIM-UHFFFAOYSA-N 4-amino-2-(4,4-dimethyl-2-oxoimidazolidin-1-yl)-n-[3-(trifluoromethyl)phenyl]pyrimidine-5-carboxamide Chemical compound O=C1NC(C)(C)CN1C(N=C1N)=NC=C1C(=O)NC1=CC=CC(C(F)(F)F)=C1 FUSNOPLQVRUIIM-UHFFFAOYSA-N 0.000 claims description 14
- 229910000377 hydrazine sulfate Inorganic materials 0.000 claims description 14
- 239000012493 hydrazine sulfate Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 6
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 3
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 2
- 239000012266 salt solution Substances 0.000 claims description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims 1
- 238000002271 resection Methods 0.000 claims 1
- 238000009987 spinning Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- PLZBFOLWMGDYMX-UHFFFAOYSA-N CN(N)C(C1=CC=C(C(=O)NN)C=C1)=O Chemical compound CN(N)C(C1=CC=C(C(=O)NN)C=C1)=O PLZBFOLWMGDYMX-UHFFFAOYSA-N 0.000 description 3
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000015271 coagulation Effects 0.000 description 2
- 238000005345 coagulation Methods 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- 239000007863 gel particle Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- YWLJDTQPCLQYFL-UHFFFAOYSA-N 2-methylbenzene-1,4-dicarbohydrazide Chemical compound CC1=C(C(=O)NN)C=CC(=C1)C(=O)NN YWLJDTQPCLQYFL-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- VFTOLAKHPLTCIF-UHFFFAOYSA-N aminoazanium;dihydrogen phosphate Chemical compound NN.OP(O)(O)=O VFTOLAKHPLTCIF-UHFFFAOYSA-N 0.000 description 1
- UTTHLMXOSUFZCQ-UHFFFAOYSA-N benzene-1,3-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC(C(=O)NN)=C1 UTTHLMXOSUFZCQ-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000701 coagulant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000012447 hatching Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002531 isophthalic acids Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAWFFNJAPKXVPH-UHFFFAOYSA-N naphthalene-1,6-dicarboxylic acid Chemical class OC(=O)C1=CC=CC2=CC(C(=O)O)=CC=C21 VAWFFNJAPKXVPH-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229920005594 polymer fiber Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 239000004753 textile Substances 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Artificial Filaments (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20259071A | 1971-11-26 | 1971-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2257706A1 true DE2257706A1 (de) | 1973-05-30 |
Family
ID=22750518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722257706 Pending DE2257706A1 (de) | 1971-11-26 | 1972-11-24 | Verfahren zur herstellung aromatischer oxadiazol/n-alkylhydrazid-polymerisate |
Country Status (11)
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046731A (en) | 1976-05-13 | 1977-09-06 | Monsanto Company | Process for preparing dopes from which shaped articles of oxadiazole/N-alkylhydrazide copolymers are obtained |
| US4054633A (en) * | 1976-05-13 | 1977-10-18 | Monsanto Company | Process for continuously preparing shaped articles of aromatic oxadiazole or aromatic oxadiazole/N-alkylhydrazide polymers from monomer solutions |
| FR2370116A1 (fr) * | 1976-11-05 | 1978-06-02 | Monsanto Co | Procede d'etirage a chaud de files de copolymeres oxadiazole aromatique/n-alkylhydrazide et nouveaux produits ainsi obtenus |
| FR2371532A1 (enrdf_load_stackoverflow) * | 1976-11-18 | 1978-06-16 | Monsanto Co | |
| US4118358A (en) * | 1977-03-10 | 1978-10-03 | Monsanto Company | Preparation of oxadiazole copolymer solution from scrap copolymer |
| US7582721B2 (en) * | 2006-05-01 | 2009-09-01 | E.I. Du Pont De Nemours And Company | Two step preparation of random polyoxadiazole copolymer and articles resulting therefrom |
| US7528216B2 (en) * | 2006-05-01 | 2009-05-05 | E.I. Du Pont De Nemours And Company | Two step preparation of random polyoxadiazole copolymer and articles resulting therefrom |
| US7618707B2 (en) * | 2007-08-22 | 2009-11-17 | E.I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from diamino diphenyl sulfone and modacrylic fibers and fabrics and garments made therefrom and methods for making same |
| US7700190B2 (en) * | 2007-08-22 | 2010-04-20 | E.I. Du Pont De Nemours And Company | Flame resistant spun staple yarns made from blends of fibers derived from diamino diphenyl sulfone and textile fibers and fabrics and garments made therefrom and methods for making same |
| CN112979947B (zh) * | 2021-05-13 | 2021-08-20 | 陈瑾 | 芳香族聚噁二唑、芳香族聚噁二唑薄膜及薄膜的制备方法 |
-
0
- BE BE791894D patent/BE791894A/xx unknown
-
1972
- 1972-11-23 NL NL7215868A patent/NL7215868A/xx not_active Application Discontinuation
- 1972-11-24 GB GB5432472A patent/GB1407439A/en not_active Expired
- 1972-11-24 BR BR828872A patent/BR7208288D0/pt unknown
- 1972-11-24 CA CA157,495A patent/CA990889A/en not_active Expired
- 1972-11-24 IT IT3208372A patent/IT972260B/it active
- 1972-11-24 FR FR7241927A patent/FR2161089B1/fr not_active Expired
- 1972-11-24 LU LU66555D patent/LU66555A1/xx unknown
- 1972-11-24 DE DE19722257706 patent/DE2257706A1/de active Pending
- 1972-11-24 AT AT1004572A patent/AT323426B/de not_active IP Right Cessation
- 1972-11-25 JP JP11849772A patent/JPS4860800A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NL7215868A (enrdf_load_stackoverflow) | 1973-05-29 |
| JPS4860800A (enrdf_load_stackoverflow) | 1973-08-25 |
| FR2161089A1 (enrdf_load_stackoverflow) | 1973-07-06 |
| GB1407439A (en) | 1975-09-24 |
| FR2161089B1 (enrdf_load_stackoverflow) | 1975-06-13 |
| LU66555A1 (enrdf_load_stackoverflow) | 1973-06-08 |
| AU4926372A (en) | 1974-06-06 |
| IT972260B (it) | 1974-05-20 |
| AT323426B (de) | 1975-07-10 |
| BE791894A (fr) | 1973-05-24 |
| BR7208288D0 (pt) | 1973-09-25 |
| CA990889A (en) | 1976-06-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |