CA2078848A1 - Process for preparing arylene sulfide polymers - Google Patents
Process for preparing arylene sulfide polymersInfo
- Publication number
- CA2078848A1 CA2078848A1 CA002078848A CA2078848A CA2078848A1 CA 2078848 A1 CA2078848 A1 CA 2078848A1 CA 002078848 A CA002078848 A CA 002078848A CA 2078848 A CA2078848 A CA 2078848A CA 2078848 A1 CA2078848 A1 CA 2078848A1
- Authority
- CA
- Canada
- Prior art keywords
- alkali metal
- bisulfide
- reaction product
- hydrogen sulfide
- reaction
- 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.)
- Abandoned
Links
- -1 arylene sulfide Chemical compound 0.000 title claims abstract description 75
- 229920000642 polymer Polymers 0.000 title claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 97
- 239000000203 mixture Substances 0.000 claims abstract description 94
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims abstract description 57
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims abstract description 57
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 51
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 33
- 150000003951 lactams Chemical class 0.000 claims abstract description 32
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 238000013022 venting Methods 0.000 claims abstract description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 105
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 43
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 8
- PDMUBVHXTYNLDT-UHFFFAOYSA-M sodium;4-(methylamino)butanoate Chemical compound [Na+].CNCCCC([O-])=O PDMUBVHXTYNLDT-UHFFFAOYSA-M 0.000 claims description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 7
- 239000007791 liquid phase Substances 0.000 claims description 7
- 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 claims description 7
- 239000001632 sodium acetate Substances 0.000 claims description 7
- 235000017281 sodium acetate Nutrition 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 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 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims description 2
- ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- IBSGAWQJFSDRBJ-UHFFFAOYSA-M cesium sulfanide Chemical compound [SH-].[Cs+] IBSGAWQJFSDRBJ-UHFFFAOYSA-M 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 150000004816 dichlorobenzenes Chemical class 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- HXQGSILMFTUKHI-UHFFFAOYSA-M lithium;sulfanide Chemical compound S[Li] HXQGSILMFTUKHI-UHFFFAOYSA-M 0.000 claims description 2
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 claims description 2
- ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 claims description 2
- LXOXXUIVMOYGST-UHFFFAOYSA-M rubidium(1+);sulfanide Chemical compound [SH-].[Rb+] LXOXXUIVMOYGST-UHFFFAOYSA-M 0.000 claims description 2
- ZWXPDGCFMMFNRW-UHFFFAOYSA-N N-methylcaprolactam Chemical compound CN1CCCCCC1=O ZWXPDGCFMMFNRW-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 239000004734 Polyphenylene sulfide Substances 0.000 description 12
- 230000018044 dehydration Effects 0.000 description 9
- 238000006297 dehydration reaction Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 7
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000005406 washing Methods 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
- 239000012535 impurity Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 125000002877 alkyl aryl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000011010 flushing procedure Methods 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-M hydrosulfide Chemical compound [SH-] RWSOTUBLDIXVET-UHFFFAOYSA-M 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910052701 rubidium Inorganic materials 0.000 description 2
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 2
- CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- MBFGXWLPCQHIHT-UHFFFAOYSA-N (4-methylphenyl) acetate;potassium Chemical compound [K].CC(=O)OC1=CC=C(C)C=C1 MBFGXWLPCQHIHT-UHFFFAOYSA-N 0.000 description 1
- ZLELNPSBDOUFHN-UHFFFAOYSA-N 1,2,3,4-tetrachloro-5-methylbenzene Chemical compound CC1=CC(Cl)=C(Cl)C(Cl)=C1Cl ZLELNPSBDOUFHN-UHFFFAOYSA-N 0.000 description 1
- SOZFIIXUNAKEJP-UHFFFAOYSA-N 1,2,3,4-tetrafluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1F SOZFIIXUNAKEJP-UHFFFAOYSA-N 0.000 description 1
- UURGNCIPRITNBJ-UHFFFAOYSA-N 1,2,3,5-tetrachloro-4-methylbenzene Chemical compound CC1=C(Cl)C=C(Cl)C(Cl)=C1Cl UURGNCIPRITNBJ-UHFFFAOYSA-N 0.000 description 1
- QZYNWJQFTJXIRN-UHFFFAOYSA-N 1,2,3,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C(Cl)=C1 QZYNWJQFTJXIRN-UHFFFAOYSA-N 0.000 description 1
- UHHYOKRQTQBKSB-UHFFFAOYSA-N 1,2,3,5-tetrafluorobenzene Chemical compound FC1=CC(F)=C(F)C(F)=C1 UHHYOKRQTQBKSB-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
- AJKNNUJQFALRIK-UHFFFAOYSA-N 1,2,3-trifluorobenzene Chemical compound FC1=CC=CC(F)=C1F AJKNNUJQFALRIK-UHFFFAOYSA-N 0.000 description 1
- UNKZCXQBGMGLDG-UHFFFAOYSA-N 1,2,4,5-tetrabutyl-3,6-dichlorobenzene Chemical compound CCCCC1=C(Cl)C(CCCC)=C(CCCC)C(Cl)=C1CCCC UNKZCXQBGMGLDG-UHFFFAOYSA-N 0.000 description 1
- ZOXPZFFPPKVNEA-UHFFFAOYSA-N 1,2,4,5-tetrachloro-3-methylbenzene Chemical compound CC1=C(Cl)C(Cl)=CC(Cl)=C1Cl ZOXPZFFPPKVNEA-UHFFFAOYSA-N 0.000 description 1
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 description 1
- SDXUIOOHCIQXRP-UHFFFAOYSA-N 1,2,4,5-tetrafluorobenzene Chemical compound FC1=CC(F)=C(F)C=C1F SDXUIOOHCIQXRP-UHFFFAOYSA-N 0.000 description 1
- PEBWOGPSYUIOBP-UHFFFAOYSA-N 1,2,4-trifluorobenzene Chemical compound FC1=CC=C(F)C(F)=C1 PEBWOGPSYUIOBP-UHFFFAOYSA-N 0.000 description 1
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 1
- XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
- JORVCRLRRRRLFI-UHFFFAOYSA-N 1,3-dichloro-2-fluorobenzene Chemical compound FC1=C(Cl)C=CC=C1Cl JORVCRLRRRRLFI-UHFFFAOYSA-N 0.000 description 1
- ASWQRHRFJXTXBJ-UHFFFAOYSA-N 1,4-dibromo-2-butyl-5-ethylbenzene Chemical compound CCCCC1=CC(Br)=C(CC)C=C1Br ASWQRHRFJXTXBJ-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
- 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
- AFNHODZKFRGAOZ-UHFFFAOYSA-N 1-(3-methylphenyl)azetidin-2-one Chemical compound CC1=CC=CC(N2C(CC2)=O)=C1 AFNHODZKFRGAOZ-UHFFFAOYSA-N 0.000 description 1
- GNFCNQUBONBCLF-UHFFFAOYSA-N 1-benzyl-4-(2-methylphenyl)piperidin-2-one Chemical compound CC1=CC=CC=C1C1CC(=O)N(CC=2C=CC=CC=2)CC1 GNFCNQUBONBCLF-UHFFFAOYSA-N 0.000 description 1
- LVUQCTGSDJLWCE-UHFFFAOYSA-N 1-benzylpyrrolidin-2-one Chemical compound O=C1CCCN1CC1=CC=CC=C1 LVUQCTGSDJLWCE-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
- YZJKRCHJFHUTTK-UHFFFAOYSA-N 1-butyl-2,5-dichloro-3-ethylbenzene Chemical compound CCCCC1=CC(Cl)=CC(CC)=C1Cl YZJKRCHJFHUTTK-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
- NNAACTNLZAIIBF-UHFFFAOYSA-N 1-cyclopentyl-4-dodecylpiperidin-2-one Chemical compound O=C1CC(CCCCCCCCCCCC)CCN1C1CCCC1 NNAACTNLZAIIBF-UHFFFAOYSA-N 0.000 description 1
- DXRBTWLMBZCLBV-UHFFFAOYSA-N 1-dodecyl-3-octylpyrrolidin-2-one Chemical compound CCCCCCCCCCCCN1CCC(CCCCCCCC)C1=O DXRBTWLMBZCLBV-UHFFFAOYSA-N 0.000 description 1
- VUQMOERHEHTWPE-UHFFFAOYSA-N 1-ethylpiperidin-2-one Chemical compound CCN1CCCCC1=O VUQMOERHEHTWPE-UHFFFAOYSA-N 0.000 description 1
- YHNQOXAUNKFXNZ-UHFFFAOYSA-N 13-amino-tridecanoic acid Chemical compound NCCCCCCCCCCCCC(O)=O YHNQOXAUNKFXNZ-UHFFFAOYSA-N 0.000 description 1
- BDJZCCWUSOZUQG-UHFFFAOYSA-N 2,4-dichloro-1-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1Cl BDJZCCWUSOZUQG-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
- YSEQNZOXHCKLOG-UHFFFAOYSA-N 2-methyl-octanoic acid Chemical compound CCCCCCC(C)C(O)=O YSEQNZOXHCKLOG-UHFFFAOYSA-N 0.000 description 1
- SCTNORZYAHACCZ-UHFFFAOYSA-M 3-phenyl-5-(propan-2-ylamino)pentanoate;rubidium(1+) Chemical compound [Rb+].CC(C)NCCC(CC([O-])=O)C1=CC=CC=C1 SCTNORZYAHACCZ-UHFFFAOYSA-M 0.000 description 1
- BNWOFLCLCRHUTF-UHFFFAOYSA-N 3-phenylpyrrolidin-2-one Chemical compound O=C1NCCC1C1=CC=CC=C1 BNWOFLCLCRHUTF-UHFFFAOYSA-N 0.000 description 1
- AOKCDAVWJLOAHG-UHFFFAOYSA-N 4-(methylamino)butyric acid Chemical compound C[NH2+]CCCC([O-])=O AOKCDAVWJLOAHG-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RSTNUXHTAATHED-UHFFFAOYSA-N 8-(butylamino)-4-cyclohexyl-7-methyloctanoic acid Chemical compound CCCCNCC(C)CCC(CCC(O)=O)C1CCCCC1 RSTNUXHTAATHED-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 241001208007 Procas Species 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000004280 Sodium formate Substances 0.000 description 1
- 241000613130 Tima Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 1
- JUPQTSLXMOCDHR-UHFFFAOYSA-N benzene-1,4-diol;bis(4-fluorophenyl)methanone Chemical compound OC1=CC=C(O)C=C1.C1=CC(F)=CC=C1C(=O)C1=CC=C(F)C=C1 JUPQTSLXMOCDHR-UHFFFAOYSA-N 0.000 description 1
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 1
- HYWCISCKYCCFMI-UHFFFAOYSA-M butanoate;rubidium(1+) Chemical compound [Rb+].CCCC([O-])=O HYWCISCKYCCFMI-UHFFFAOYSA-M 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- UVNJSVAENMDAJH-UHFFFAOYSA-M cesium;6-[butyl(cyclohexyl)amino]-3-propan-2-ylhexanoate Chemical compound [Cs+].[O-]C(=O)CC(C(C)C)CCCN(CCCC)C1CCCCC1 UVNJSVAENMDAJH-UHFFFAOYSA-M 0.000 description 1
- NMKVMUXQLXZRNQ-UHFFFAOYSA-M cesium;hexanoate Chemical compound [Cs+].CCCCCC([O-])=O NMKVMUXQLXZRNQ-UHFFFAOYSA-M 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- YFVBKGHJQCMDBL-UHFFFAOYSA-N cyclohexyl acetate;potassium Chemical compound [K].CC(=O)OC1CCCCC1 YFVBKGHJQCMDBL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012035 limiting reagent Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- XNGMTHGDRFOBKZ-UHFFFAOYSA-M lithium;13-(hexylamino)-6-pentyltridecanoate Chemical compound [Li+].CCCCCCNCCCCCCCC(CCCCC)CCCCC([O-])=O XNGMTHGDRFOBKZ-UHFFFAOYSA-M 0.000 description 1
- KBBLDDQLOMDTBN-UHFFFAOYSA-M lithium;2-aminoacetate Chemical compound [Li+].NCC([O-])=O KBBLDDQLOMDTBN-UHFFFAOYSA-M 0.000 description 1
- IIDVGIFOWJJSIJ-UHFFFAOYSA-M lithium;2-methylpropanoate Chemical compound [Li+].CC(C)C([O-])=O IIDVGIFOWJJSIJ-UHFFFAOYSA-M 0.000 description 1
- ZSICDRPAYOOLQB-UHFFFAOYSA-M lithium;2-phenylacetate Chemical compound [Li+].[O-]C(=O)CC1=CC=CC=C1 ZSICDRPAYOOLQB-UHFFFAOYSA-M 0.000 description 1
- OYTJIZNGQNUSAK-UHFFFAOYSA-M lithium;cyclohexanecarboxylate Chemical compound [Li+].[O-]C(=O)C1CCCCC1 OYTJIZNGQNUSAK-UHFFFAOYSA-M 0.000 description 1
- RQZHWDLISAJCLK-UHFFFAOYSA-M lithium;heptanoate Chemical compound [Li+].CCCCCCC([O-])=O RQZHWDLISAJCLK-UHFFFAOYSA-M 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
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052754 neon Inorganic materials 0.000 description 1
- GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- KMDZMULKSSIOGW-UHFFFAOYSA-M potassium;2-(nonylamino)tetradecanoate Chemical compound [K+].CCCCCCCCCCCCC(C([O-])=O)NCCCCCCCCC KMDZMULKSSIOGW-UHFFFAOYSA-M 0.000 description 1
- HIDKSOTTZRMUML-UHFFFAOYSA-M potassium;dodecanoate Chemical compound [K+].CCCCCCCCCCCC([O-])=O HIDKSOTTZRMUML-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 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
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
- 235000019254 sodium formate Nutrition 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 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
- SQVYXHWTMXOMAF-UHFFFAOYSA-M sodium;10-(cyclopentylamino)-4-hexyldecanoate Chemical compound [Na+].CCCCCCC(CCC([O-])=O)CCCCCCNC1CCCC1 SQVYXHWTMXOMAF-UHFFFAOYSA-M 0.000 description 1
- FWPKLBJSNSLJTB-UHFFFAOYSA-M sodium;2-(dimethylamino)propanoate Chemical compound [Na+].CN(C)C(C)C([O-])=O FWPKLBJSNSLJTB-UHFFFAOYSA-M 0.000 description 1
- QEYVBRNXWJOTDZ-UHFFFAOYSA-M sodium;3-(2-methylanilino)-4-phenylbutanoate Chemical compound [Na+].CC1=CC=CC=C1NC(CC([O-])=O)CC1=CC=CC=C1 QEYVBRNXWJOTDZ-UHFFFAOYSA-M 0.000 description 1
- XJVTZYPZLDTIHI-UHFFFAOYSA-M sodium;4-(cyclohexylamino)butanoate Chemical compound [Na+].[O-]C(=O)CCCNC1CCCCC1 XJVTZYPZLDTIHI-UHFFFAOYSA-M 0.000 description 1
- KZLZZCGWFHFJMT-UHFFFAOYSA-M sodium;4-(decylamino)dodecanoate Chemical compound [Na+].CCCCCCCCCCNC(CCC([O-])=O)CCCCCCCC KZLZZCGWFHFJMT-UHFFFAOYSA-M 0.000 description 1
- KDGFSUSPVCYLFX-UHFFFAOYSA-M sodium;4-phenylcyclohexane-1-carboxylate Chemical compound [Na+].C1CC(C(=O)[O-])CCC1C1=CC=CC=C1 KDGFSUSPVCYLFX-UHFFFAOYSA-M 0.000 description 1
- AYWPLQVAAFRCHO-UHFFFAOYSA-M sodium;5-aminopentanoate Chemical compound [Na+].NCCCCC([O-])=O AYWPLQVAAFRCHO-UHFFFAOYSA-M 0.000 description 1
- XMMCSLXNQAIBRQ-UHFFFAOYSA-M sodium;6-(methylamino)hexanoate Chemical compound [Na+].CNCCCCCC([O-])=O XMMCSLXNQAIBRQ-UHFFFAOYSA-M 0.000 description 1
- LHYPLJGBYPAQAK-UHFFFAOYSA-M sodium;pentanoate Chemical compound [Na+].CCCCC([O-])=O LHYPLJGBYPAQAK-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000005303 weighing 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
- 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
-
- 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
- C08G75/0259—Preparatory processes metal hydrogensulfides
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76402391A | 1991-09-23 | 1991-09-23 | |
| US07/764,023 | 1991-09-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2078848A1 true CA2078848A1 (en) | 1993-03-24 |
Family
ID=25069467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002078848A Abandoned CA2078848A1 (en) | 1991-09-23 | 1992-09-22 | Process for preparing arylene sulfide polymers |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0534359A1 (enExample) |
| JP (1) | JPH05202189A (enExample) |
| KR (1) | KR930006075A (enExample) |
| CA (1) | CA2078848A1 (enExample) |
| TW (1) | TW223086B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020183481A1 (en) * | 1999-12-30 | 2002-12-05 | Vidaurri Fernando C. | Method to decrease corrosiveness of reactants in poly(arylene sulfide) polymer production |
| JP4742525B2 (ja) * | 2004-06-25 | 2011-08-10 | 東レ株式会社 | ポリフェニレンスルフィド樹脂組成物 |
| CN111533910A (zh) * | 2020-05-11 | 2020-08-14 | 山东滨化滨阳燃化有限公司 | 一种注塑级聚苯硫醚树脂的工业化生产工艺及装置 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3867356A (en) * | 1973-11-19 | 1975-02-18 | Phillips Petroleum Co | Arylene sulfide polymers |
| US3884884A (en) * | 1973-11-20 | 1975-05-20 | Phillips Petroleum Co | Arylene sulfide polymers |
| US4324886A (en) * | 1980-05-06 | 1982-04-13 | Phillips Petroleum Company | Arylene sulfide polymer prepared from aminoalkanoate |
| US4373090A (en) * | 1982-02-16 | 1983-02-08 | Phillips Petroleum Company | Arylene sulfide polymer preparation |
| US4451643A (en) * | 1983-01-06 | 1984-05-29 | Phillips Petroleum Company | Production of arylene sulfide polymer beads |
| US5023315A (en) * | 1990-04-18 | 1991-06-11 | Phillips Peteroleum Company | Process for preparing arylene sulfide polymers |
-
1992
- 1992-07-10 JP JP4183781A patent/JPH05202189A/ja active Pending
- 1992-07-20 KR KR1019920012912A patent/KR930006075A/ko not_active Withdrawn
- 1992-07-21 TW TW081105750A patent/TW223086B/zh active
- 1992-09-22 EP EP92116165A patent/EP0534359A1/en not_active Withdrawn
- 1992-09-22 CA CA002078848A patent/CA2078848A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0534359A1 (en) | 1993-03-31 |
| KR930006075A (ko) | 1993-04-20 |
| TW223086B (enExample) | 1994-05-01 |
| JPH05202189A (ja) | 1993-08-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4767841A (en) | Arylene sulfide polymer preparation from dehydrated admixture comprising sulfur source, cyclic amide solvent and water | |
| US4786711A (en) | P-phenylene sulfide polymer preparation with dehydrated mixture of alkali metal hydroxide and excess alkali metal bisulfide | |
| US4282347A (en) | Preparation of branched polymers of arylene sulfide | |
| US4089847A (en) | Temperature programming in the production of arylene sulfide polymers | |
| US5438115A (en) | Process for preparing poly(arylene sulfide) polymers | |
| US5239050A (en) | Process for preparing arylene sulfide polymer with addition of aqueous alkali metal carboxylate prior to termination of polymerization | |
| KR100262252B1 (ko) | 폴리(아릴렌술파이드)중합체의 제조 방법 | |
| US3786035A (en) | Alkali metal sulfide-arylene sulfide polymer process | |
| US4350810A (en) | Preparation of branched chain arylene sulfide polymer | |
| CA2096652C (en) | Process for the preparation of poly(arylene sulfide) with low metal contamination and polymer produced | |
| US5175243A (en) | Process for preparing arylene sulfide polymers with halo benzene containing deactivating group | |
| US5109110A (en) | Process for the production of polyarylene sulfides with lithium halide and alkali metal hydrosulfide | |
| US4786712A (en) | Process for the preparation of optionally branched polyarylene sulphides having reduced corrosiveness with ketone diluent and organic solvent | |
| EP0280271A2 (en) | Arylene sulfide polymers | |
| CA2078848A1 (en) | Process for preparing arylene sulfide polymers | |
| EP0100551B1 (en) | Arylene sulfide terpolymers and processes for making them | |
| US4464507A (en) | Process for the production of high molecular weight, optionally branched, polyarylene sulphides | |
| JPH04275334A (ja) | フェニレンスルフィドポリマーの製造法 | |
| CA2079939C (en) | Limiting the amount of water during the polymerization of phenylene sulfide polymers | |
| US4882416A (en) | Preparation of poly arylene sulfide with specified ratio of sulfur source to cyclic organic amide | |
| US5064936A (en) | Process for preparing high extrusion rate arylene sulfide polymers | |
| US5159056A (en) | Preparation of arylene sulfide polymer in the presence of titanium dioxide | |
| CA1336729C (en) | Poly(arylene sulfide)s and preparation thereof | |
| EP1242508B1 (en) | Method to decrease corrosiveness of reactants in poly(arylene sulfide) polymer production | |
| EP0487103B1 (en) | Process for preparing arylene sulfide polymers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 19960323 |