CN1793202A - Tech., for polymerizing fibre grade polyphenyl sulfoether resin - Google Patents
Tech., for polymerizing fibre grade polyphenyl sulfoether resin Download PDFInfo
- Publication number
- CN1793202A CN1793202A CNA2005100224376A CN200510022437A CN1793202A CN 1793202 A CN1793202 A CN 1793202A CN A2005100224376 A CNA2005100224376 A CN A2005100224376A CN 200510022437 A CN200510022437 A CN 200510022437A CN 1793202 A CN1793202 A CN 1793202A
- Authority
- CN
- China
- Prior art keywords
- acid
- sodium
- fiber
- polyphenyl thioether
- grade polyphenyl
- 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.)
- Granted
Links
- 229920005989 resin Polymers 0.000 title claims abstract description 26
- 239000011347 resin Substances 0.000 title claims abstract description 26
- 229920006389 polyphenyl polymer Polymers 0.000 title claims abstract description 12
- 239000000835 fiber Substances 0.000 title abstract description 19
- 230000000379 polymerizing effect Effects 0.000 title abstract 4
- VFNGKCDDZUSWLR-UHFFFAOYSA-N disulfuric acid Chemical compound OS(=O)(=O)OS(O)(=O)=O VFNGKCDDZUSWLR-UHFFFAOYSA-N 0.000 title 1
- 238000005516 engineering process Methods 0.000 claims abstract description 12
- 150000003568 thioethers Chemical class 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 7
- 238000005406 washing Methods 0.000 claims abstract description 7
- 239000002994 raw material Substances 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- 239000008367 deionised water Substances 0.000 claims abstract description 5
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 5
- 230000000694 effects Effects 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 19
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 19
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 10
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- 230000003750 conditioning effect Effects 0.000 claims description 8
- 238000006116 polymerization reaction Methods 0.000 claims description 8
- 235000010265 sodium sulphite Nutrition 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000006068 polycondensation reaction Methods 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 238000009987 spinning Methods 0.000 claims description 7
- 239000012752 auxiliary agent Substances 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- -1 phosphorous acid ester Chemical class 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 239000012747 synergistic agent Substances 0.000 claims description 6
- 238000010792 warming Methods 0.000 claims description 6
- 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 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
- 208000005156 Dehydration Diseases 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- 235000019270 ammonium chloride Nutrition 0.000 claims description 4
- 239000010953 base metal Substances 0.000 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 235000010755 mineral Nutrition 0.000 claims description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 4
- 230000003252 repetitive effect Effects 0.000 claims description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 4
- 239000012279 sodium borohydride Substances 0.000 claims description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 2
- CMVQZRLQEOAYSW-UHFFFAOYSA-N 1,2-dichloro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1Cl CMVQZRLQEOAYSW-UHFFFAOYSA-N 0.000 claims description 2
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 claims description 2
- BYPIKLIXBPMDBY-UHFFFAOYSA-N 2-hydroxypropanoic acid;potassium Chemical compound [K].CC(O)C(O)=O BYPIKLIXBPMDBY-UHFFFAOYSA-N 0.000 claims description 2
- JHUFGBSGINLPOW-UHFFFAOYSA-N 3-chloro-4-(trifluoromethoxy)benzoyl cyanide Chemical compound FC(F)(F)OC1=CC=C(C(=O)C#N)C=C1Cl JHUFGBSGINLPOW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052582 BN Inorganic materials 0.000 claims description 2
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 claims description 2
- PQUCIEFHOVEZAU-UHFFFAOYSA-N Diammonium sulfite Chemical compound [NH4+].[NH4+].[O-]S([O-])=O PQUCIEFHOVEZAU-UHFFFAOYSA-N 0.000 claims description 2
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 claims description 2
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 claims description 2
- 235000011130 ammonium sulphate Nutrition 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 claims description 2
- 239000001639 calcium acetate Substances 0.000 claims description 2
- 235000011092 calcium acetate Nutrition 0.000 claims description 2
- 229960005147 calcium acetate Drugs 0.000 claims description 2
- 229940117389 dichlorobenzene Drugs 0.000 claims description 2
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 claims description 2
- YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 claims description 2
- 229940071161 dodecylbenzenesulfonate Drugs 0.000 claims description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 claims description 2
- 235000013905 glycine and its sodium salt Nutrition 0.000 claims description 2
- 239000004247 glycine and its sodium salt Substances 0.000 claims description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 2
- 235000011147 magnesium chloride Nutrition 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 2
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 claims description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 2
- 229940067157 phenylhydrazine Drugs 0.000 claims description 2
- 229920000642 polymer Polymers 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 238000011112 process operation Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 235000015424 sodium Nutrition 0.000 claims description 2
- 229940029258 sodium glycinate Drugs 0.000 claims description 2
- 235000010288 sodium nitrite Nutrition 0.000 claims description 2
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 claims description 2
- WUWHFEHKUQVYLF-UHFFFAOYSA-M sodium;2-aminoacetate Chemical compound [Na+].NCC([O-])=O WUWHFEHKUQVYLF-UHFFFAOYSA-M 0.000 claims description 2
- 239000004334 sorbic acid Substances 0.000 claims description 2
- 235000010199 sorbic acid Nutrition 0.000 claims description 2
- 229940075582 sorbic acid Drugs 0.000 claims description 2
- 239000008117 stearic acid Substances 0.000 claims description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 claims description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 claims description 2
- 229960001763 zinc sulfate Drugs 0.000 claims description 2
- 229910000368 zinc sulfate Inorganic materials 0.000 claims description 2
- HSYFJDYGOJKZCL-UHFFFAOYSA-L zinc;sulfite Chemical compound [Zn+2].[O-]S([O-])=O HSYFJDYGOJKZCL-UHFFFAOYSA-L 0.000 claims description 2
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 claims 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 claims 3
- NPDACUSDTOMAMK-UHFFFAOYSA-N 4-Chlorotoluene Chemical compound CC1=CC=C(Cl)C=C1 NPDACUSDTOMAMK-UHFFFAOYSA-N 0.000 claims 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims 1
- JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 claims 1
- ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 claims 1
- BLNVISNJTIRAHF-UHFFFAOYSA-N 4-chlorobenzamide Chemical compound NC(=O)C1=CC=C(Cl)C=C1 BLNVISNJTIRAHF-UHFFFAOYSA-N 0.000 claims 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 claims 1
- 125000003963 dichloro group Chemical group Cl* 0.000 claims 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical compound CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 claims 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 claims 1
- 229940090668 parachlorophenol Drugs 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- BYQADQLDVPAGSR-UHFFFAOYSA-N toluene;hydrobromide Chemical compound Br.CC1=CC=CC=C1 BYQADQLDVPAGSR-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 abstract 2
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 239000000178 monomer Substances 0.000 abstract 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 6
- 229920013632 Ryton Polymers 0.000 description 5
- 239000004736 Ryton® Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- 101100074998 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-2 gene Proteins 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 238000005201 scrubbing Methods 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 206010016654 Fibrosis Diseases 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000004761 fibrosis Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
Landscapes
- Artificial Filaments (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a fiber grade polyphenyl thioether resin polymerizing technology that uses sodium sulfide and P-DCB as raw material, condensation polymerizing to form PPS monomer under the effect of alkali metal catalyst. The following process would improve the sinnability of the resin: taking dehydrating process to sodium sulfide, adding assistant agent, heating to 200-275 degree centigrade, taking polymerizing reaction for 6-8 hours; adding regulator at 155-180 degree centigrade and heating to 210-275 degree centigrade, whisking for 0.5 hour, taking at least one time of filtering and washing, adding synergist; washing by deionized water, taking drying process to gain the improved polyphenyl thioether resin.
Description
Affiliated technical field
The invention belongs to the macromolecule resin production field.
Background technology
High-performance polyphenylene sulfide has the thermostability under excellent chemical proofing and the high temperature, and has fire-retardant, insulation, radiation hardness and favorable mechanical performance.For enlarging the use range of this material, the investigators of various countries make it the novel method that fibrosis is used in searching always.
Chinese patent CN91107114 discloses a kind of potassium titanate fiber and the compound processing method of making matrix material of polyphenylene sulfide, in polycondensation vessel, at first use six polyamine dispersant (the synthetic solvent of using of double as polyphenylene sulfide) under heating and agitation condition, potassium titanate fiber to be disperseed, adding sodium sulphite and santochlor (P-DCB) then is raw material, (sodium sulphite and santochlor (P-DCB) are raw material to polycondensation production polyphenylene sulfide, and the fibre composite of polyphenylene sulfide (PPS) and potassium titanate fiber is produced in polycondensation under the base metal catalysts effect under the base metal catalysts effect.But this method makes the shortcoming that has the fibre breakage intensity difference.U.S. Pat 5401799 discloses a kind of polyphenylene sulfide based thermoplastic glass conjugated fibre with high-wearing feature, and composition of raw materials is provided.
With regard to the situation of prior art, the mode of matrix material is generally adopted in the manufacturing of polyphenylene sulfide fibre, though there is report U.S. Phillipsd company that the fiber-grade polyphenyl thioether production of resins is arranged, does not see the introduction of concrete technology.
The objective of the invention is to study a kind of fiber-grade polyphenyl thioether resin polymerization technology, improve the spinning property of resin, make the fiber manufacturing in later stage obtain the better properties index then by choose reasonable technic index, auxiliary agent, conditioning agent, synergistic agent.
Summary of the invention
The objective of the invention is to realize by following means.
Fiber-grade polyphenyl thioether resin polymerization technology, adopting sodium sulphite and santochlor (P-DCB) is raw material, polycondensation is produced in the monomeric technological process of polyphenylene sulfide (PPS) under the base metal catalysts effect, adopts following processing condition to improve the spinning property of the resin slicer of gained:
1) the sodium sulphite processed stage adds auxiliary agent, stirs slow intensification 2-6 hour down, is warming up to 200 ℃ of dehydrations;
2) polycondensation phase behind the adding dichlorobenzene adds conditioning agent, if be warming up to 200-275 ℃, polyreaction 6-8 hour;
3) through 1) 2) mixture that obtains of step, add conditioning agents down at 155 ~ 185 ℃, be warmed up to 210 ℃ again and continue to stir 0.5 hour.
4) through 1), 2), 3) mixture that obtains of step, after 100 ~ 200 ℃ of filtrations, the filtration-washing repetitive process operation more than once again, and add synergistic agent in stirring is washed through deionized water again.
1) through 1), 2), 3), 4) polyphenylene sulfide that obtains having better spinning property after the step resulting polymers drying treatment.
After adopting means as above, the crystallization of the resin of acquisition is more good, and spinning property improves, the breaking tenacity of the fiber that makes, and use temperature and oxygen index are improved.
Description of drawings:
Fig. 1 is the fibre resin index synopsis 1 of the Ryton of the resin that obtains of the present invention and Phillipsd company.
Fig. 2 is the fibre resin index synopsis 2 of the Ryton of the resin that obtains of the present invention and Phillipsd company.
Embodiment
Below in conjunction with embodiment technology of the present invention is described in further detail.
Embodiment 1
In autoclave, add N-methyl-2 pyrrolidone (NMP) 12 kilograms, sodium sulphite (Na
2S.3H
2O) 44 kilograms, 0.01 kilogram of sodium borohydride (auxiliary agent), under the 0.01Mpa nitrogen gas pressure, stir on one side, heat up on one side, rise to 200 ℃ of dehydrations with 2 hours times, add 4.15 kilograms of santochlor again, the NMP2 kilogram, the nitro dichlorobenzene is warming up to 200 ℃ for 0.15 kilogram, 8 hours postcooling of polyreaction.185 ℃ add and are warmed up to 250 ℃ of processing after 0.1 kilogram of hexanodioic acid carries out, and mixture is after 140 ℃ of filtrations.With 40 liters of branches of deionized water 8 times the polymkeric substance that makes is carried out repetitive scrubbing, filtration, first and second time washing adds 0.1 kilogram of ammonium chloride respectively, the 4th washing adds 0.05 kilogram of synergistic agent quadrol tetrem disodium, dry down at 100 ℃ then, obtain 2.05 kilograms of polyphenylene sulfides, flow rate 172g/10min (ASTM-1238-70), 283.5 ℃ of fusing points, ash 0.27%, volatile matter 0.28% (150 ℃), Mw52589, polydispersity coefficient PD2.19.
Embodiment 2
In autoclave, add N-methyl-2 pyrrolidone (NMP) 12 kilograms, sodium sulphite (Na
2S.3H
2O) 4 kilograms, 0.01 kilogram of sodium borohydride, under the 0.01MPa nitrogen gas pressure, stir on one side, heat up on one side, rise to 200 ℃ of dehydrations with 2 hours times, add 4.10 kilograms of santochlor again, the NMP2 kilogram is warming up to 275 ℃ to 0.17 kilogram of Histol, 6 hours postcooling of polyreaction.185 ℃ add and are warmed up to 250 ℃ of processing after 0.1 kilogram of hexanodioic acid carries out, mixture carries out repetitive scrubbing, filtration with 40 liters of branches of deionized water 8 times to the polymkeric substance that makes after 140 ℃ of filtrations, first and second time washing adds 0.1 kilogram of ammonium chloride respectively, adds 0.05 kilogram of quadrol tetrem disodium the 4th time.Dry under 100 ℃ then, obtain 2.1 kilograms of polyphenylene sulfides. flow rate 168g/10min (ASTM-1238-70), 283.0 ℃ of fusing points, ash 0.25%, volatile matter 0.27% (150 ℃), Mw47685, polydispersity coefficient PD2.4.
The resin of this explained hereafter is linear right-polyphenylene sulfide, and spinning property is superior, and the key technical indexes of the polyphenylene sulfide fibre that makes is good.
The fibre resin index of the fibre-grade PPS resin of its acquisition and the Ryton of Phillipsd company is relatively as table 1, by finding out in the table 1, the product sample 20021209 that the inventive method makes and 20021104 flow rate, ash and volatile matter index are all than the Ryton of Phillipsd company
TME2481 is low, therefore has more better spinnability energy.
The fiber of being made by resin of the present invention is by the detection to index of correlation of Sichuan Province examination of fibers office and national fire-proof construction material quality surveillance inspection center, the Ryton fiber of measurement result and Phillipsd company more as shown in Table 2,
As above contrast as seen, the product that the present invention obtains has better spinnability, and the fiber decapacitation that makes keeps the characteristic of PPS itself such as the chemical resistant properties of excellence, thermotolerance, outside the flame retardant resistance etc., also have more favorable mechanical performance, and its corresponding index all can reach international like product index.
In addition, in actual production, auxiliary agent can be a kind of of following material or several:
The material of the strong reducing power of tool: as formaldehyde, acetaldehyde, sodium borohydride, POTASSIUM BOROHYDRIDE, Thiovanic acid, hydrazine hydrate, phenylhydrazine, pyrodin, phosphorous acid ester, Sodium Nitrite, boron nitride, 4, the two sulfonyl hydrazides of 4-oxo etc.
Conditioning agent can be a kind of of following material or several:
Organic acid or mineral acid: as palmitinic acid, citric acid, lauric acid, hexanodioic acid, butyric acid, n-nonanoic acid,, Sorbic Acid, stearic acid, toxilic acid, pentanedioic acid, mineral acid such as sulfuric acid, hydrochloric acid, etc.
Synergistic agent can be a kind of of following material or several:
The carboxylate salt of alkali or alkaline-earth metal or strong acid weak base salt, sulfonate: as ammonium sulfate, magnesium chloride, ammonium chloride, ammonium sulphite, zinc sulfate, zinc sulfite, zinc chloride, sebacic acid penta 2 ammoniums, ammonium nitrate, Soduxin, hexanodioic acid sodium, disodium EDTA, calcium acetate, Sodium Glycinate, hydroxy-propionic acid potassium, tetrasodium ethylenediamine tetraacetate, dodecylbenzene sulfonate, sodium allyl sulfonate, sodium cetanesulfonate etc.
Claims (5)
1, fiber-grade polyphenyl thioether resin polymerization technology is raw material adopting sodium sulphite and santochlor, and polycondensation is produced in the monomeric technological process of polyphenylene sulfide under the base metal catalysts effect, adopts following processing condition to improve the spinning property of the resin slicer of gained:
1) in the sodium sulphite processed stage, add auxiliary agent, stirred slow intensification 2-6 hour down, be warming up to 200 ℃ of dehydrations;
2) polycondensation phase behind the adding dichlorobenzene adds conditioning agent, is warming up to 200-275 ℃, polyreaction 6-8 hour;
3) through 1), 2) mixture that obtains of step, add conditioning agents down at 155 ~ 180 ℃ and be warmed up to 210 ~ 275 ℃ again and continue to stir 0.5 hour.
4) through 1), 2), 3) mixture that obtains of step, after 100 ~ 200 ℃ of filtrations, the filtration-washing repetitive process operation more than once again, and add synergistic agent in the agitator treating process is washed through deionized water again;
Through 1), 2), 3), 4) polyphenylene sulfide that obtains having better spinning property after the step resulting polymers drying treatment.
2, the fiber-grade polyphenyl thioether resin polymerization technology according to claim 1 is characterized in that, described auxiliary agent can be a kind of of following material or several:
The material of the strong reducing power of tool: as formaldehyde, acetaldehyde, sodium borohydride, POTASSIUM BOROHYDRIDE, Thiovanic acid, hydrazine hydrate, phenylhydrazine, pyrodin, phosphorous acid ester, Sodium Nitrite, boron nitride, 4, the two sulfonyl hydrazides of 4-oxo etc.
According to claim 1 or 2 described fiber-grade polyphenyl thioether resin polymerization technologies, it is characterized in that 3, described conditioning agent can be a kind of of following material or several:
The compound of halogenated aromatic, aminated compounds, phenols: as parachlorotoluene, ortho-chlorotolu'ene, chlorobenzene, toluene bromide, nitro dichlorobenzene, orthodichlorobenzene, Meta Dichlorobenzene, phenylenediamine, hexanediamine, 1,2,4-trichlorobenzene, orthodichlorobenzene, m-dibromobenzene, 2,5 dichloro benzosulfonic acid sodium, bromobenzene, iodobenzene, aniline, para-totuidine, p-Chlorobenzoic acid amide, para-chlorophenol, phenol, p-cresol, Ortho Cresol, to Histol etc.
4, the fiber-grade polyphenyl thioether resin polymerization technology according to claim 3 is characterized in that, described conditioning agent can be a kind of of following material or several:
Organic acid or mineral acid: as palmitinic acid, citric acid, lauric acid, hexanodioic acid, butyric acid, n-nonanoic acid,, Sorbic Acid, stearic acid, toxilic acid, pentanedioic acid, mineral acid such as sulfuric acid, hydrochloric acid, etc.
5, the fiber-grade polyphenyl thioether resin polymerization technology according to claim 4 is characterized in that, described synergistic agent can be a kind of of following material or several:
The carboxylate salt of alkali or alkaline-earth metal or strong acid weak base salt, sulfonate: as ammonium sulfate, magnesium chloride, ammonium chloride, ammonium sulphite, zinc sulfate, zinc sulfite, zinc chloride, sebacic acid penta 2 ammoniums, ammonium nitrate, Soduxin, hexanodioic acid sodium, disodium EDTA, calcium acetate, Sodium Glycinate, hydroxy-propionic acid potassium, tetrasodium ethylenediamine tetraacetate, dodecylbenzene sulfonate, sodium allyl sulfonate, sodium cetanesulfonate etc.
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| CN102675640A (en) * | 2011-03-18 | 2012-09-19 | 四川得阳工程塑料开发有限公司 | Method for controlling process conditions for production and synthesis of polyphenylene sulfide |
| CN102702528A (en) * | 2012-05-28 | 2012-10-03 | 自贡鸿鹤化工股份有限公司 | Production method for polyphenyl thioether |
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| JPH08120081A (en) * | 1994-10-25 | 1996-05-14 | Tonen Chem Corp | High-molecular poly(arylene sulfide) for molded sheet |
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| CN1095481C (en) * | 2000-12-27 | 2002-12-04 | 古旗高 | Process for preparing high-density high-molecular linear polyphenyl thioether |
| JP2003268105A (en) * | 2002-03-19 | 2003-09-25 | Toray Ind Inc | Method for manufacturing poly(arylene sulfide) |
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