CA1087348A - Production of arylene sulfide polymers - Google Patents
Production of arylene sulfide polymersInfo
- Publication number
- CA1087348A CA1087348A CA247,086A CA247086A CA1087348A CA 1087348 A CA1087348 A CA 1087348A CA 247086 A CA247086 A CA 247086A CA 1087348 A CA1087348 A CA 1087348A
- Authority
- CA
- Canada
- Prior art keywords
- range
- alkali metal
- dihalobenzene
- alkyl
- lithium acetate
- 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
- -1 arylene sulfide Chemical compound 0.000 title claims abstract description 51
- 229920000642 polymer Polymers 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 239000000203 mixture Substances 0.000 claims abstract description 52
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims abstract description 32
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 21
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 claims abstract description 19
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 17
- 239000002585 base Substances 0.000 claims abstract description 14
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 150000002367 halogens Chemical group 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical group ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims description 12
- IAQLJCYTGRMXMA-UHFFFAOYSA-M lithium;acetate;dihydrate Chemical compound [Li+].O.O.CC([O-])=O IAQLJCYTGRMXMA-UHFFFAOYSA-M 0.000 claims description 12
- 229910052979 sodium sulfide Inorganic materials 0.000 claims description 12
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical group [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 8
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical group ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 230000035484 reaction time Effects 0.000 claims description 7
- XWUCFAJNVTZRLE-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound C1=C(S2)C=CC2=C1 XWUCFAJNVTZRLE-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 150000003857 carboxamides Chemical class 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000007791 liquid phase Substances 0.000 claims description 5
- 239000002002 slurry Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- 208000005156 Dehydration Diseases 0.000 abstract description 32
- 230000018044 dehydration Effects 0.000 abstract description 32
- 238000006297 dehydration reaction Methods 0.000 abstract description 32
- 238000004821 distillation Methods 0.000 abstract description 23
- 238000005187 foaming Methods 0.000 abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 4
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 abstract description 3
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 238000001816 cooling Methods 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 5
- 238000003556 assay Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 230000036571 hydration Effects 0.000 description 4
- 238000006703 hydration reaction Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000000732 arylene group Chemical group 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- NAQWICRLNQSPPW-UHFFFAOYSA-N 1,2,3,4-tetrachloronaphthalene Chemical compound C1=CC=CC2=C(Cl)C(Cl)=C(Cl)C(Cl)=C21 NAQWICRLNQSPPW-UHFFFAOYSA-N 0.000 description 1
- YPFCYPZKFQPCOC-UHFFFAOYSA-N 1,2,3,5-tetrabromobenzene Chemical compound BrC1=CC(Br)=C(Br)C(Br)=C1 YPFCYPZKFQPCOC-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- DMFMMVMUXPAZKT-UHFFFAOYSA-N 1,2,4-tribromo-6-methylnaphthalene Chemical compound BrC1=C(Br)C=C(Br)C2=CC(C)=CC=C21 DMFMMVMUXPAZKT-UHFFFAOYSA-N 0.000 description 1
- KSXFNGRHPAHIQJ-UHFFFAOYSA-N 1,2,4-triiodobenzene Chemical compound IC1=CC=C(I)C(I)=C1 KSXFNGRHPAHIQJ-UHFFFAOYSA-N 0.000 description 1
- VMNISWKTOHUZQN-UHFFFAOYSA-N 1,3,5-trichloro-2,4,6-trimethylbenzene Chemical compound CC1=C(Cl)C(C)=C(Cl)C(C)=C1Cl VMNISWKTOHUZQN-UHFFFAOYSA-N 0.000 description 1
- RCTKUIOMKBEGTG-UHFFFAOYSA-N 1,3,5-trichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=C(Cl)C=C1Cl RCTKUIOMKBEGTG-UHFFFAOYSA-N 0.000 description 1
- GHVFWFCIYIGDCX-UHFFFAOYSA-N 1,4-dibromo-2-butyl-5-cyclohexylbenzene Chemical compound C1=C(Br)C(CCCC)=CC(Br)=C1C1CCCCC1 GHVFWFCIYIGDCX-UHFFFAOYSA-N 0.000 description 1
- KZHZSALFKRDIBQ-UHFFFAOYSA-N 1,4-dibromo-2-ethyl-5-propan-2-ylbenzene Chemical compound CCC1=CC(Br)=C(C(C)C)C=C1Br KZHZSALFKRDIBQ-UHFFFAOYSA-N 0.000 description 1
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- PTIQIITULDNGAF-UHFFFAOYSA-N 1,4-dichloro-2,3,5,6-tetramethylbenzene Chemical compound CC1=C(C)C(Cl)=C(C)C(C)=C1Cl PTIQIITULDNGAF-UHFFFAOYSA-N 0.000 description 1
- UTGSRNVBAFCOEU-UHFFFAOYSA-N 1,4-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C=C1Cl UTGSRNVBAFCOEU-UHFFFAOYSA-N 0.000 description 1
- WKDOCYUWLREIQL-UHFFFAOYSA-N 1,4-dichloro-2-(3-methylcyclopentyl)-5-octylbenzene Chemical compound C1=C(Cl)C(CCCCCCCC)=CC(Cl)=C1C1CC(C)CC1 WKDOCYUWLREIQL-UHFFFAOYSA-N 0.000 description 1
- KFAKZJUYBOYVKA-UHFFFAOYSA-N 1,4-dichloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Cl KFAKZJUYBOYVKA-UHFFFAOYSA-N 0.000 description 1
- LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
- DZHFFMWJXJBBRG-UHFFFAOYSA-N 1-bromo-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Br)=C1 DZHFFMWJXJBBRG-UHFFFAOYSA-N 0.000 description 1
- UCCUXODGPMAHRL-UHFFFAOYSA-N 1-bromo-4-iodobenzene Chemical compound BrC1=CC=C(I)C=C1 UCCUXODGPMAHRL-UHFFFAOYSA-N 0.000 description 1
- GWQSENYKCGJTRI-UHFFFAOYSA-N 1-chloro-4-iodobenzene Chemical compound ClC1=CC=C(I)C=C1 GWQSENYKCGJTRI-UHFFFAOYSA-N 0.000 description 1
- WFRDCUNBIGSXQA-UHFFFAOYSA-N 1-methyl-3-propylpyrrolidin-2-one Chemical compound CCCC1CCN(C)C1=O WFRDCUNBIGSXQA-UHFFFAOYSA-N 0.000 description 1
- GHELJWBGTIKZQW-UHFFFAOYSA-N 1-propan-2-ylpyrrolidin-2-one Chemical compound CC(C)N1CCCC1=O GHELJWBGTIKZQW-UHFFFAOYSA-N 0.000 description 1
- DCALJVULAGICIX-UHFFFAOYSA-N 1-propylpyrrolidin-2-one Chemical compound CCCN1CCCC1=O DCALJVULAGICIX-UHFFFAOYSA-N 0.000 description 1
- QORAVNMWUNPXAO-UHFFFAOYSA-N 2,2',4,4'-tetrachlorobiphenyl Chemical group ClC1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1Cl QORAVNMWUNPXAO-UHFFFAOYSA-N 0.000 description 1
- ZWMYTAHVFFRQTD-UHFFFAOYSA-N 2,4-dibromo-3-(2,6-dibromo-3,5-dimethylphenyl)-1,5-dimethylbenzene Chemical group CC1=CC(C)=C(Br)C(C=2C(=C(C)C=C(C)C=2Br)Br)=C1Br ZWMYTAHVFFRQTD-UHFFFAOYSA-N 0.000 description 1
- YDUZJJVOMVPPMD-UHFFFAOYSA-N 2,5-dichloro-1-dodecyl-3-hexylbenzene Chemical compound CCCCCCCCCCCCC1=CC(Cl)=CC(CCCCCC)=C1Cl YDUZJJVOMVPPMD-UHFFFAOYSA-N 0.000 description 1
- PMOATLADBGHBMF-UHFFFAOYSA-N 2-(2,5-diiodophenyl)-1,4-diiodobenzene Chemical group IC1=CC=C(I)C(C=2C(=CC=C(I)C=2)I)=C1 PMOATLADBGHBMF-UHFFFAOYSA-N 0.000 description 1
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
- ZXONXKTYRSSVKY-UHFFFAOYSA-N 2-benzyl-1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C(CC=2C=CC=CC=2)=C1 ZXONXKTYRSSVKY-UHFFFAOYSA-N 0.000 description 1
- SHJDOXMERQRWDJ-UHFFFAOYSA-N 4-bromo-1-chloro-2-phenylbenzene Chemical compound ClC1=CC=C(Br)C=C1C1=CC=CC=C1 SHJDOXMERQRWDJ-UHFFFAOYSA-N 0.000 description 1
- MYYYNTZMFMWVKT-UHFFFAOYSA-N 5-ethyl-1,3-dimethylpyrrolidin-2-one Chemical compound CCC1CC(C)C(=O)N1C MYYYNTZMFMWVKT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- QTNDMWXOEPGHBT-UHFFFAOYSA-N dicesium;sulfide Chemical compound [S-2].[Cs+].[Cs+] QTNDMWXOEPGHBT-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000005171 halobenzenes Chemical class 0.000 description 1
- CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- GLNWILHOFOBOFD-UHFFFAOYSA-N lithium sulfide Chemical compound [Li+].[Li+].[S-2] GLNWILHOFOBOFD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- WPFGFHJALYCVMO-UHFFFAOYSA-L rubidium carbonate Chemical compound [Rb+].[Rb+].[O-]C([O-])=O WPFGFHJALYCVMO-UHFFFAOYSA-L 0.000 description 1
- 229910000026 rubidium carbonate Inorganic materials 0.000 description 1
- AHKSSQDILPRNLA-UHFFFAOYSA-N rubidium(1+);sulfide Chemical compound [S-2].[Rb+].[Rb+] AHKSSQDILPRNLA-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RNOOGJGHUVNWNC-UHFFFAOYSA-N sodium;sulfide Chemical compound [Na+].[S-2] RNOOGJGHUVNWNC-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance 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
- 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
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
- C08G75/0254—Preparatory processes using metal sulfides
-
- 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
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0231—Polyarylenethioethers containing chain-terminating or chain-branching agents
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58133175A | 1975-05-27 | 1975-05-27 | |
| US581,331 | 1975-05-27 | ||
| US642,098 | 1976-01-19 | ||
| US05/642,098 US4064114A (en) | 1975-05-27 | 1976-01-19 | Production of arylene sulfide polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1087348A true CA1087348A (en) | 1980-10-07 |
Family
ID=27078291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA247,086A Expired CA1087348A (en) | 1975-05-27 | 1976-03-04 | Production of arylene sulfide polymers |
Country Status (11)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4116947A (en) * | 1977-04-29 | 1978-09-26 | Phillips Petroleum Company | Branched arylene sulfide polymer production |
| DE3019732A1 (de) * | 1980-05-23 | 1981-12-03 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von polyarylensulfiden |
| JPS57137346A (en) * | 1981-02-18 | 1982-08-24 | Toray Ind Inc | Thermoplastic polyester resin |
| JPS58206632A (ja) * | 1982-05-28 | 1983-12-01 | Dainippon Ink & Chem Inc | ポリフエニレンスルフイドの製造方法 |
| AU544880B2 (en) * | 1982-08-03 | 1985-06-20 | Phillips Petroleum Co. | Arylene sulphide terpolymers |
| JPS5925822A (ja) * | 1982-08-04 | 1984-02-09 | Dainippon Ink & Chem Inc | ポリフエニレンスルフイドの製造方法 |
| DE3243189A1 (de) * | 1982-11-23 | 1984-05-24 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hochmolekularen gegebenenfalls verzweigten polyarylensulfiden |
| DE3312254A1 (de) * | 1983-04-05 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von gegebenenfalls verzweigten polyarylensulfiden |
| DE3312284A1 (de) * | 1983-04-05 | 1984-10-11 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von gegebenenfalls verzweigten polyarylensulfiden |
| DE3318401A1 (de) * | 1983-05-20 | 1984-11-22 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hochmolekularen, gegebenenfalls verzweigten polyarylensulfiden |
| DE3339233A1 (de) * | 1983-10-28 | 1985-05-09 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von gegebenenfalls verzweigten polyarylensulfiden mit verminderter korrosivitaet |
| JPS60119277U (ja) * | 1984-01-20 | 1985-08-12 | 林 利雄 | 円柱を三角錐に組立るパツキン |
| DE3426918A1 (de) * | 1984-07-21 | 1986-01-23 | Bayer Ag, 5090 Leverkusen | Faserverstaerktes polyphenylensulfid |
| DE3428985A1 (de) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hochmolekularen, gegebenenfalls verzweigten polyarylensulfiden |
| DE3428986A1 (de) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hochmolekularen, gegebenenfalls verzweigten polyarylensulfiden |
| DE3428984A1 (de) * | 1984-08-07 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hochmolekularen, gegebenenfalls verzweigten polyarylensulfiden |
| JPH0649761B2 (ja) * | 1985-12-18 | 1994-06-29 | 東ソー株式会社 | ポリフエニレンサルフアイドの製造方法 |
| JPS6353260U (enrdf_load_stackoverflow) * | 1986-09-24 | 1988-04-09 | ||
| JP2792653B2 (ja) * | 1988-04-28 | 1998-09-03 | 東ソー株式会社 | ポリフェニレンスルフィドの製造方法 |
| CA2102477A1 (en) * | 1992-11-24 | 1994-05-25 | Paul J. Deslauriers | Compositions comprising sulfur-containing derivatives of hydroxyphenylbenzotriazole and process therefor |
| CN112513143B (zh) | 2018-08-29 | 2021-08-27 | 株式会社吴羽 | 连续脱水方法以及聚亚芳基硫醚的制造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| DE2053313A1 (de) * | 1970-10-30 | 1972-05-04 | Hess Sb Automatenbau Gmbh | Brühvorrichtung fur Kaffeemaschine |
| US3763124A (en) * | 1971-06-21 | 1973-10-02 | Phillips Petroleum Co | Treatment of the alkali metal sulfide reactant to reduce impurities and its reaction with a polyhalo substituted aromatic compound |
| US3786035A (en) * | 1972-05-15 | 1974-01-15 | Phillips Petroleum Co | Alkali metal sulfide-arylene sulfide polymer process |
-
1976
- 1976-03-04 CA CA247,086A patent/CA1087348A/en not_active Expired
- 1976-05-20 JP JP51058456A patent/JPS51144496A/ja active Granted
- 1976-05-21 ES ES448119A patent/ES448119A1/es not_active Expired
- 1976-05-24 NO NO761764A patent/NO140890C/no unknown
- 1976-05-25 DE DE2623333A patent/DE2623333C2/de not_active Expired
- 1976-05-26 GB GB21882/76A patent/GB1534903A/en not_active Expired
- 1976-05-26 IT IT23698/76A patent/IT1061399B/it active
- 1976-05-26 FR FR7616017A patent/FR2312525A1/fr active Granted
- 1976-05-26 DK DK231076A patent/DK156224C/da not_active IP Right Cessation
- 1976-05-26 NL NL7605676.A patent/NL167448C/xx not_active IP Right Cessation
- 1976-05-26 SE SE7606021A patent/SE414638B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE414638B (sv) | 1980-08-11 |
| DE2623333C2 (de) | 1982-12-02 |
| FR2312525B1 (enrdf_load_stackoverflow) | 1979-08-17 |
| GB1534903A (en) | 1978-12-06 |
| NL167448C (nl) | 1981-12-16 |
| IT1061399B (it) | 1983-02-28 |
| ES448119A1 (es) | 1977-07-01 |
| NL7605676A (nl) | 1976-11-30 |
| NO140890B (no) | 1979-08-27 |
| NO140890C (no) | 1979-12-05 |
| SE7606021L (sv) | 1976-11-28 |
| DK156224B (da) | 1989-07-10 |
| DK231076A (da) | 1976-11-28 |
| JPS5325589B2 (enrdf_load_stackoverflow) | 1978-07-27 |
| JPS51144496A (en) | 1976-12-11 |
| NL167448B (nl) | 1981-07-16 |
| DE2623333A1 (de) | 1976-12-09 |
| NO761764L (enrdf_load_stackoverflow) | 1976-11-30 |
| DK156224C (da) | 1989-11-20 |
| FR2312525A1 (fr) | 1976-12-24 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry | ||
| MKEX | Expiry |
Effective date: 19971007 |