JP5516241B2

JP5516241B2 - 環式ポリアリーレンスルフィドの製造方法

環式ポリアリーレンスルフィドの製造方法 Download PDF

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Publication number: JP5516241B2
Authority: JP; Japan
Prior art keywords: reaction; pas; cyclic; polyarylene sulfide; mol
Prior art date: 2009-08-31
Legal status : Active

Application number

JP2010191970A

Other languages

English (en)

Japanese (ja)

Other versions

JP2011068885A5 (enExample

JP2011068885A (ja

Inventor

俊輔堀内

佳世大澤

智幸小田島

幸二山内

Current Assignee

Toray Industries Inc

Original Assignee

Toray Industries Inc

Priority date

2009-08-31

Filing date

2010-08-30

Publication date

2014-06-11

2010-08-30 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

2010-08-30 Priority to JP2010191970A priority Critical patent/JP5516241B2/ja

2011-04-07 Publication of JP2011068885A publication Critical patent/JP2011068885A/ja

2013-08-22 Publication of JP2011068885A5 publication Critical patent/JP2011068885A5/ja

2014-06-11 Application granted granted Critical

2014-06-11 Publication of JP5516241B2 publication Critical patent/JP5516241B2/ja

Status Active legal-status Critical Current

2030-08-30 Anticipated expiration legal-status Critical

Links

125000004122 cyclic group Chemical group 0.000 title claims description 323
229920000412 polyarylene Polymers 0.000 title claims description 152
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 147
238000004519 manufacturing process Methods 0.000 title claims description 58
238000006243 chemical reaction Methods 0.000 claims description 291
239000011541 reaction mixture Substances 0.000 claims description 150
229910052717 sulfur Inorganic materials 0.000 claims description 147
239000011593 sulfur Substances 0.000 claims description 146
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 144
238000000034 method Methods 0.000 claims description 127
239000003795 chemical substances by application Substances 0.000 claims description 108
239000002798 polar solvent Substances 0.000 claims description 84
150000001491 aromatic compounds Chemical class 0.000 claims description 82
239000000203 mixture Substances 0.000 claims description 71
238000010438 heat treatment Methods 0.000 claims description 45
-1 polysiloxane Polymers 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 33
150000007944 thiolates Chemical group 0.000 claims description 13
239000003513 alkali Substances 0.000 claims description 9
125000000732 arylene group Chemical group 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
238000010992 reflux Methods 0.000 claims description 6
150000003568 thioethers Chemical class 0.000 claims description 6
229920001296 polysiloxane Polymers 0.000 claims description 2
230000019086 sulfide ion homeostasis Effects 0.000 claims description 2
239000002904 solvent Substances 0.000 description 142
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 103
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
229910001868 water Inorganic materials 0.000 description 100
239000004734 Polyphenylene sulfide Substances 0.000 description 90
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 90
229920000069 polyphenylene sulfide Polymers 0.000 description 90
239000007787 solid Substances 0.000 description 74
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 68
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 53
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 47
239000002994 raw material Substances 0.000 description 44
229920005989 resin Polymers 0.000 description 41
239000011347 resin Substances 0.000 description 41
229910052757 nitrogen Inorganic materials 0.000 description 34
239000012298 atmosphere Substances 0.000 description 29
238000000926 separation method Methods 0.000 description 28
239000007788 liquid Substances 0.000 description 26
238000006116 polymerization reaction Methods 0.000 description 26
238000003756 stirring Methods 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
239000007864 aqueous solution Substances 0.000 description 24
239000000835 fiber Substances 0.000 description 22
239000000243 solution Substances 0.000 description 22
230000002829 reductive effect Effects 0.000 description 21
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
238000004128 high performance liquid chromatography Methods 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
229910052783 alkali metal Inorganic materials 0.000 description 17
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239000000843 powder Substances 0.000 description 17
239000006227 byproduct Substances 0.000 description 16
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ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
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YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
230000001590 oxidative effect Effects 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
239000000126 substance Substances 0.000 description 14
229910052977 alkali metal sulfide Inorganic materials 0.000 description 13
239000010408 film Substances 0.000 description 13
239000000155 melt Substances 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
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229910001220 stainless steel Inorganic materials 0.000 description 13
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
239000003054 catalyst Substances 0.000 description 12
239000007789 gas Substances 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
208000005156 Dehydration Diseases 0.000 description 11
239000007795 chemical reaction product Substances 0.000 description 11
230000018044 dehydration Effects 0.000 description 11
238000006297 dehydration reaction Methods 0.000 description 11
239000012535 impurity Substances 0.000 description 11
238000007086 side reaction Methods 0.000 description 11
238000011282 treatment Methods 0.000 description 11
229920006127 amorphous resin Polymers 0.000 description 10
230000000670 limiting effect Effects 0.000 description 10
238000005259 measurement Methods 0.000 description 10
239000000178 monomer Substances 0.000 description 10
238000010791 quenching Methods 0.000 description 10
230000000171 quenching effect Effects 0.000 description 10
239000012783 reinforcing fiber Substances 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
150000008044 alkali metal hydroxides Chemical class 0.000 description 9
150000001340 alkali metals Chemical class 0.000 description 9
238000004132 cross linking Methods 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000001914 filtration Methods 0.000 description 9
230000006872 improvement Effects 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000000862 absorption spectrum Methods 0.000 description 8
238000004458 analytical method Methods 0.000 description 8
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
239000000945 filler Substances 0.000 description 8
229910000037 hydrogen sulfide Inorganic materials 0.000 description 8
238000012844 infrared spectroscopy analysis Methods 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 8
239000002184 metal Substances 0.000 description 8
238000000465 moulding Methods 0.000 description 8
239000002002 slurry Substances 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
230000008901 benefit Effects 0.000 description 7
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238000000354 decomposition reaction Methods 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
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ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
229920000642 polymer Polymers 0.000 description 7
238000011084 recovery Methods 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
229920000049 Carbon (fiber) Polymers 0.000 description 6
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
238000000944 Soxhlet extraction Methods 0.000 description 6
239000004917 carbon fiber Substances 0.000 description 6
230000000052 comparative effect Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
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150000004677 hydrates Chemical class 0.000 description 6
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
150000003457 sulfones Chemical class 0.000 description 6
229910001508 alkali metal halide Inorganic materials 0.000 description 5
150000008045 alkali metal halides Chemical class 0.000 description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 5
229920001400 block copolymer Polymers 0.000 description 5
239000002131 composite material Substances 0.000 description 5
238000000605 extraction Methods 0.000 description 5
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229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
239000011261 inert gas Substances 0.000 description 5
150000002576 ketones Chemical class 0.000 description 5
238000004898 kneading Methods 0.000 description 5
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
239000001301 oxygen Substances 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
229920005604 random copolymer Polymers 0.000 description 5
229910052979 sodium sulfide Inorganic materials 0.000 description 5
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 5
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
229910001873 dinitrogen Inorganic materials 0.000 description 4
238000004090 dissolution Methods 0.000 description 4
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
239000012530 fluid Substances 0.000 description 4
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230000009477 glass transition Effects 0.000 description 4
239000001307 helium Substances 0.000 description 4
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SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 4
238000002347 injection Methods 0.000 description 4
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229910003475 inorganic filler Inorganic materials 0.000 description 4
239000011256 inorganic filler Substances 0.000 description 4
AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
229920000193 polymethacrylate Polymers 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
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238000001542 size-exclusion chromatography Methods 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
238000002411 thermogravimetry Methods 0.000 description 4
150000003573 thiols Chemical class 0.000 description 4
239000002699 waste material Substances 0.000 description 4
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238000009736 wetting Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
XWUCFAJNVTZRLE-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]hepta-1,3,5-triene Chemical group C1=C(S2)C=CC2=C1 XWUCFAJNVTZRLE-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
239000002585 base Substances 0.000 description 3
239000003990 capacitor Substances 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
239000003086 colorant Substances 0.000 description 3
238000013329 compounding Methods 0.000 description 3
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239000007822 coupling agent Substances 0.000 description 3
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238000010908 decantation Methods 0.000 description 3
238000009826 distribution Methods 0.000 description 3
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239000000446 fuel Substances 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
150000008040 ionic compounds Chemical class 0.000 description 3
HXQGSILMFTUKHI-UHFFFAOYSA-M lithium;sulfanide Chemical compound S[Li] HXQGSILMFTUKHI-UHFFFAOYSA-M 0.000 description 3
239000000463 material Substances 0.000 description 3
238000010128 melt processing Methods 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
239000004417 polycarbonate Substances 0.000 description 3
229920000515 polycarbonate Polymers 0.000 description 3
229920001225 polyester resin Polymers 0.000 description 3
239000004645 polyester resin Substances 0.000 description 3
239000001103 potassium chloride Substances 0.000 description 3
235000011164 potassium chloride Nutrition 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000376 reactant Substances 0.000 description 3
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229920005992 thermoplastic resin Polymers 0.000 description 3
239000013585 weight reducing agent Substances 0.000 description 3
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 2
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 2
QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
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239000004215 Carbon black (E152) Substances 0.000 description 2
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
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239000004696 Poly ether ether ketone Substances 0.000 description 2
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239000002202 Polyethylene glycol Substances 0.000 description 2
239000004721 Polyphenylene oxide Substances 0.000 description 2
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SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
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GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
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