GB1600911A - Process for the preparation of arylene sulfide polymers - Google Patents
Process for the preparation of arylene sulfide polymers Download PDFInfo
- Publication number
- GB1600911A GB1600911A GB16999/78A GB1699978A GB1600911A GB 1600911 A GB1600911 A GB 1600911A GB 16999/78 A GB16999/78 A GB 16999/78A GB 1699978 A GB1699978 A GB 1699978A GB 1600911 A GB1600911 A GB 1600911A
- Authority
- GB
- United Kingdom
- Prior art keywords
- water
- alkali metal
- process according
- metal sulfide
- mixture
- 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
- 238000000034 method Methods 0.000 title claims description 49
- -1 arylene sulfide Chemical compound 0.000 title claims description 48
- 229920000642 polymer Polymers 0.000 title claims description 37
- 238000002360 preparation method Methods 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 73
- 229910052977 alkali metal sulfide Inorganic materials 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 34
- 239000011734 sodium Substances 0.000 claims description 31
- 229910052708 sodium Inorganic materials 0.000 claims description 27
- 150000001491 aromatic compounds Chemical class 0.000 claims description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 16
- 230000036571 hydration Effects 0.000 claims description 13
- 238000006703 hydration reaction Methods 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical group [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000001632 sodium acetate Substances 0.000 claims description 5
- 235000017281 sodium acetate Nutrition 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 229940117389 dichlorobenzene Drugs 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000003951 lactams Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- QTNDMWXOEPGHBT-UHFFFAOYSA-N dicesium;sulfide Chemical compound [S-2].[Cs+].[Cs+] QTNDMWXOEPGHBT-UHFFFAOYSA-N 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000007942 carboxylates Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229910052701 rubidium Inorganic materials 0.000 claims 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 23
- 150000002367 halogens Chemical group 0.000 description 13
- 229910052979 sodium sulfide Inorganic materials 0.000 description 13
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 13
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 9
- 239000000155 melt Substances 0.000 description 8
- 229920000069 polyphenylene sulfide Polymers 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 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 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- AOGQPLXWSUTHQB-UHFFFAOYSA-N hexyl acetate Chemical compound CCCCCCOC(C)=O AOGQPLXWSUTHQB-UHFFFAOYSA-N 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000243 solution Substances 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
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-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
- BSJWDQYZFBYNIM-UHFFFAOYSA-N 1,3,4,5-tetramethylpyrrolidin-2-one Chemical compound CC1C(C)N(C)C(=O)C1C BSJWDQYZFBYNIM-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
- BCNBMSZKALBQEF-UHFFFAOYSA-N 1,3-dimethylpyrrolidin-2-one Chemical compound CC1CCN(C)C1=O BCNBMSZKALBQEF-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
- YYJPEAJXCVEBFA-UHFFFAOYSA-N 1,6-diethylpiperidin-2-one Chemical compound CCC1CCCC(=O)N1CC YYJPEAJXCVEBFA-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
- GWCFTYITFDWLAY-UHFFFAOYSA-N 1-ethylazepan-2-one Chemical compound CCN1CCCCCC1=O GWCFTYITFDWLAY-UHFFFAOYSA-N 0.000 description 1
- ORJPENRDMJCWPF-UHFFFAOYSA-N 1-methyl-5-propan-2-ylpiperidin-2-one Chemical compound CC(C)C1CCC(=O)N(C)C1 ORJPENRDMJCWPF-UHFFFAOYSA-N 0.000 description 1
- KSAYPHFACZGEAZ-UHFFFAOYSA-N 1-methyl-7-propan-2-ylazepan-2-one Chemical compound CC(C)C1CCCCC(=O)N1C KSAYPHFACZGEAZ-UHFFFAOYSA-N 0.000 description 1
- GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-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
- TVASIXIEZMALMA-UHFFFAOYSA-N 1-propylazepane Chemical compound CCCN1CCCCCC1 TVASIXIEZMALMA-UHFFFAOYSA-N 0.000 description 1
- DCALJVULAGICIX-UHFFFAOYSA-N 1-propylpyrrolidin-2-one Chemical compound CCCN1CCCC1=O DCALJVULAGICIX-UHFFFAOYSA-N 0.000 description 1
- HLQDGCWIOSOMDP-UHFFFAOYSA-N 2,3,4,5-tetrachlorobiphenyl Chemical group ClC1=C(Cl)C(Cl)=CC(C=2C=CC=CC=2)=C1Cl HLQDGCWIOSOMDP-UHFFFAOYSA-N 0.000 description 1
- DRYYJQYUHPRVBN-UHFFFAOYSA-N 3-ethyl-1-methylpiperidin-2-one Chemical compound CCC1CCCN(C)C1=O DRYYJQYUHPRVBN-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
- GZJMMGYPZJBREK-UHFFFAOYSA-N 5-ethyl-1-methylazepan-2-one Chemical compound CCC1CCN(C)C(=O)CC1 GZJMMGYPZJBREK-UHFFFAOYSA-N 0.000 description 1
- GJVUSSOAEPIXJT-UHFFFAOYSA-N 5-methyl-1-propylazepan-2-one Chemical compound CCCN1CCC(C)CCC1=O GJVUSSOAEPIXJT-UHFFFAOYSA-N 0.000 description 1
- LYHJRIBBKADLEU-UHFFFAOYSA-N 5-methyl-1-propylpyrrolidin-2-one Chemical compound CCCN1C(C)CCC1=O LYHJRIBBKADLEU-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- ITIONVBQFUNVJV-UHFFFAOYSA-N Etomidoline Chemical compound C12=CC=CC=C2C(=O)N(CC)C1NC(C=C1)=CC=C1OCCN1CCCCC1 ITIONVBQFUNVJV-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- CKDDRHZIAZRDBW-UHFFFAOYSA-N henicosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCC(O)=O CKDDRHZIAZRDBW-UHFFFAOYSA-N 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
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- GPSDUZXPYCFOSQ-UHFFFAOYSA-M m-toluate Chemical compound CC1=CC=CC(C([O-])=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-M 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 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 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- AHKSSQDILPRNLA-UHFFFAOYSA-N rubidium(1+);sulfide Chemical compound [S-2].[Rb+].[Rb+] AHKSSQDILPRNLA-UHFFFAOYSA-N 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- MFBOGIVSZKQAPD-UHFFFAOYSA-M sodium butyrate Chemical compound [Na+].CCCC([O-])=O MFBOGIVSZKQAPD-UHFFFAOYSA-M 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- UDWXLZLRRVQONG-UHFFFAOYSA-M sodium hexanoate Chemical compound [Na+].CCCCCC([O-])=O UDWXLZLRRVQONG-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940006198 sodium phenylacetate Drugs 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- XRZMWBBJRQOWEB-UHFFFAOYSA-M sodium;2-(4-methylphenyl)acetate Chemical compound [Na+].CC1=CC=C(CC([O-])=O)C=C1 XRZMWBBJRQOWEB-UHFFFAOYSA-M 0.000 description 1
- VEMHGAILIPPHPB-UHFFFAOYSA-M sodium;2-cyclohexylacetate Chemical compound [Na+].[O-]C(=O)CC1CCCCC1 VEMHGAILIPPHPB-UHFFFAOYSA-M 0.000 description 1
- CHAQZFGXPLBFOT-UHFFFAOYSA-M sodium;2-methyloctanoate Chemical compound [Na+].CCCCCCC(C)C([O-])=O CHAQZFGXPLBFOT-UHFFFAOYSA-M 0.000 description 1
- GBBPFRKNGUDLLB-UHFFFAOYSA-M sodium;cyclododecanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCCCCCCCC1 GBBPFRKNGUDLLB-UHFFFAOYSA-M 0.000 description 1
- XTIVBOWLUYDHKE-UHFFFAOYSA-M sodium;cyclohexanecarboxylate Chemical compound [Na+].[O-]C(=O)C1CCCCC1 XTIVBOWLUYDHKE-UHFFFAOYSA-M 0.000 description 1
- NMTDPTPUELYEPL-UHFFFAOYSA-M sodium;heptanoate Chemical compound [Na+].CCCCCCC([O-])=O NMTDPTPUELYEPL-UHFFFAOYSA-M 0.000 description 1
- LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 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)
- Compositions Of Macromolecular Compounds (AREA)
- Artificial Filaments (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/792,172 US4116947A (en) | 1977-04-29 | 1977-04-29 | Branched arylene sulfide polymer production |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1600911A true GB1600911A (en) | 1981-10-21 |
Family
ID=25156026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16999/78A Expired GB1600911A (en) | 1977-04-29 | 1978-04-28 | Process for the preparation of arylene sulfide polymers |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4116947A (https=) |
| JP (1) | JPS53136100A (https=) |
| BE (1) | BE869843A (https=) |
| DE (1) | DE2817731C2 (https=) |
| FR (1) | FR2388846A1 (https=) |
| GB (1) | GB1600911A (https=) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4282347A (en) * | 1979-08-14 | 1981-08-04 | Phillips Petroleum Company | Preparation of branched polymers of arylene sulfide |
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| JPS59204657A (ja) * | 1983-05-09 | 1984-11-20 | Toray Ind Inc | ポリフエニレンスルフイド組成物 |
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| US5268451A (en) * | 1988-05-26 | 1993-12-07 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for the preparation of cross-linked polyarylene sulfide |
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| MY109689A (en) * | 1988-08-05 | 1997-04-30 | Idemitsu Petrochemical Company Ltd | Polyarlene sulfides, a process for preparing the same and a resin composition containing the same. |
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| CA2004259A1 (en) * | 1988-12-13 | 1990-06-13 | Kenneth C. Hoover | Higher molecular weight arylene sulfide resin and process for its preparation |
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| CA2011683C (en) * | 1989-04-03 | 1994-10-11 | Fay W. Bailey | Blow-molded polyphenylene sulfide articles |
| JP2513513B2 (ja) * | 1990-01-19 | 1996-07-03 | 呉羽化学工業株式会社 | ポリアリ―レンスルフィドの製造方法 |
| US5003033A (en) * | 1990-04-06 | 1991-03-26 | Phillips Petroleum Company | Process for preparing branched poly(arylene sulfide ketone) |
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| US5109102A (en) * | 1990-10-31 | 1992-04-28 | Phillips Petroleum Company | Preparation of arylene sulfide ketone polymers |
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| US5239051A (en) * | 1991-10-07 | 1993-08-24 | Phillips Petroleum Company | Limiting the amount of water during the preparation of phenylene sulfide polymers |
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| US5342920A (en) * | 1991-12-17 | 1994-08-30 | Tonen Chemical Corporation | Process for the preparation of polyarylene sulfide and an apparatus for the preparation thereof |
| US5235032A (en) * | 1991-12-19 | 1993-08-10 | Phillips Petroleum Company | Process for the preparation of poly(arylene sulfide) with low metal contamination |
| US5280104A (en) * | 1992-06-30 | 1994-01-18 | Phillips Petroleum Company | Process for the preparation of poly(arylene sulfide) with low metal contamination and polymer produced |
| EP1505100A4 (en) * | 2002-05-08 | 2007-04-04 | Idemitsu Kosan Co | METHOD FOR CONTINUOUS PRODUCTION OF BRANCHED POLYARYLENEULFIDES |
| EP2554569A4 (en) * | 2010-03-31 | 2016-09-07 | Kureha Corp | BRANCHED POLYARYLENE SULFIDE RESIN AND PROCESS FOR PRODUCING THE SAME |
| US20130317159A1 (en) | 2012-05-22 | 2013-11-28 | Chevron Phillips Chemical Company Lp | Reinforced Poly(Arylene Sulfide) Compositions |
| US9388282B2 (en) | 2013-10-29 | 2016-07-12 | Solvay Specialty Polymers Usa, Llc. | Method of thiophenol removal from poly(arylene sulfide) polymer compositions |
| US20150166731A1 (en) | 2013-12-16 | 2015-06-18 | Chevron Phillips Chemical Company Lp | Reinforced Poly(Arylene Sulfide) Polymer Compositions |
| US20150175748A1 (en) | 2013-12-19 | 2015-06-25 | Chevron Phillips Chemical Company Lp | Process for Production of Poly(Arylene Sulfide) |
| US20150376339A1 (en) | 2014-06-27 | 2015-12-31 | Solvay Sa | Process for Production of Poly(Arylene Sulfide) |
| EP3717565A1 (en) | 2017-11-30 | 2020-10-07 | Solvay Specialty Polymers USA, LLC | Impact-modified poly(arylene sulfide) compositions |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1056226A (en) * | 1963-11-27 | 1967-01-25 | Phillips Petroleum Co | Amylene sulfide polymers |
| US3354129A (en) * | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
| FR1437406A (fr) * | 1963-11-27 | 1966-05-06 | Phillips Petroleum Co | Procédé de production de composés contenant du soufre, ainsi que d'un composé polymérisé, à partir de composés aromatiques |
| US3790536A (en) * | 1972-09-18 | 1974-02-05 | Phillips Petroleum Co | Arylene sulfide polymer process |
| US3919177A (en) * | 1973-11-19 | 1975-11-11 | Phillips Petroleum Co | P-phenylene sulfide polymers |
| US4038262A (en) * | 1975-05-27 | 1977-07-26 | Phillips Petroleum Company | Production of arylene sulfide polymers |
| US4038261A (en) * | 1975-05-27 | 1977-07-26 | Phillips Petroleum Company | Production of branched arylene sulfide polymers |
| CA1087348A (en) * | 1975-05-27 | 1980-10-07 | James T. Edmonds, Jr. | Production of arylene sulfide polymers |
| US4102875A (en) * | 1976-06-22 | 1978-07-25 | Phillips Petroleum Company | Aromatic sulfide/sulfone polymer production |
-
1977
- 1977-04-29 US US05/792,172 patent/US4116947A/en not_active Expired - Lifetime
-
1978
- 1978-04-22 DE DE2817731A patent/DE2817731C2/de not_active Expired
- 1978-04-28 FR FR7812806A patent/FR2388846A1/fr active Granted
- 1978-04-28 GB GB16999/78A patent/GB1600911A/en not_active Expired
- 1978-05-01 JP JP5260478A patent/JPS53136100A/ja active Granted
- 1978-08-18 BE BE189965A patent/BE869843A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57334B2 (https=) | 1982-01-06 |
| FR2388846A1 (fr) | 1978-11-24 |
| DE2817731C2 (de) | 1991-04-18 |
| JPS53136100A (en) | 1978-11-28 |
| DE2817731A1 (de) | 1978-11-02 |
| US4116947A (en) | 1978-09-26 |
| BE869843A (fr) | 1979-02-19 |
| FR2388846B1 (https=) | 1983-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19970428 |