JPS6362548B2 - - Google Patents
Info
- Publication number
- JPS6362548B2 JPS6362548B2 JP24757884A JP24757884A JPS6362548B2 JP S6362548 B2 JPS6362548 B2 JP S6362548B2 JP 24757884 A JP24757884 A JP 24757884A JP 24757884 A JP24757884 A JP 24757884A JP S6362548 B2 JPS6362548 B2 JP S6362548B2
- Authority
- JP
- Japan
- Prior art keywords
- ion
- carbon atoms
- group
- bis
- fluorine
- 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
- 239000000203 mixture Substances 0.000 claims description 33
- 229920001971 elastomer Polymers 0.000 claims description 24
- 239000000806 elastomer Substances 0.000 claims description 23
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 22
- 229910052731 fluorine Inorganic materials 0.000 claims description 22
- 239000011737 fluorine Substances 0.000 claims description 22
- -1 halogen ion Chemical group 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical group FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 4
- 150000004692 metal hydroxides Chemical class 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 3
- 150000004706 metal oxides Chemical class 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical group [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical group [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- 229940006477 nitrate ion Drugs 0.000 claims description 2
- 229940005654 nitrite ion Drugs 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical group [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- 229940006280 thiosulfate ion Drugs 0.000 claims description 2
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical group [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 claims description 2
- 238000004073 vulcanization Methods 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 19
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 14
- 230000006835 compression Effects 0.000 description 10
- 238000007906 compression Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UJNZOIKQAUQOCN-UHFFFAOYSA-N methyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C)C1=CC=CC=C1 UJNZOIKQAUQOCN-UHFFFAOYSA-N 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- LLOXZCFOAUCDAE-UHFFFAOYSA-N 2-diphenylphosphorylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(P(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LLOXZCFOAUCDAE-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- UZCPNEBHTFYJNY-UHFFFAOYSA-N benzyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1CP(C=1C=CC=CC=1)C1=CC=CC=C1 UZCPNEBHTFYJNY-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- FZCLYMHCCZQKOE-UHFFFAOYSA-N (4-chlorophenyl)methyl-diphenylphosphane Chemical compound C1=CC(Cl)=CC=C1CP(C=1C=CC=CC=1)C1=CC=CC=C1 FZCLYMHCCZQKOE-UHFFFAOYSA-N 0.000 description 2
- NDMMKOCNFSTXRU-UHFFFAOYSA-N 1,1,2,3,3-pentafluoroprop-1-ene Chemical compound FC(F)C(F)=C(F)F NDMMKOCNFSTXRU-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007824 aliphatic compounds Chemical class 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- ZDKQBOZXSUXNDI-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl-diphenylphosphane Chemical compound CC1=C(CP(C2=CC=CC=C2)C2=CC=CC=C2)C=CC(=C1)C ZDKQBOZXSUXNDI-UHFFFAOYSA-N 0.000 description 1
- BYRGACBVFWPIFM-UHFFFAOYSA-N (4-bromophenyl)methyl-diphenylphosphane Chemical compound C1=CC(Br)=CC=C1CP(C=1C=CC=CC=1)C1=CC=CC=C1 BYRGACBVFWPIFM-UHFFFAOYSA-N 0.000 description 1
- SVDZDXBQOBWHLE-UHFFFAOYSA-N (4-fluorophenyl)phosphane Chemical compound FC1=CC=C(P)C=C1 SVDZDXBQOBWHLE-UHFFFAOYSA-N 0.000 description 1
- IBTPYQRLYBREMH-UHFFFAOYSA-N (4-methoxyphenyl)methyl-diphenylphosphane Chemical compound C1=CC(OC)=CC=C1CP(C=1C=CC=CC=1)C1=CC=CC=C1 IBTPYQRLYBREMH-UHFFFAOYSA-N 0.000 description 1
- XLAIWHIOIFKLEO-UHFFFAOYSA-N (E)-4-<2-(4-hydroxyphenyl)ethenyl>phenol Natural products C1=CC(O)=CC=C1C=CC1=CC=C(O)C=C1 XLAIWHIOIFKLEO-UHFFFAOYSA-N 0.000 description 1
- XHGMOUXCWNPJHF-UHFFFAOYSA-N 1,1-difluoroethene;1,1,2,3,3,3-hexafluoroprop-1-ene;1,1,2,2-tetrafluoroethene Chemical group FC(F)=C.FC(F)=C(F)F.FC(F)=C(F)C(F)(F)F XHGMOUXCWNPJHF-UHFFFAOYSA-N 0.000 description 1
- DMUPYMORYHFFCT-UHFFFAOYSA-N 1,2,3,3,3-pentafluoroprop-1-ene Chemical compound FC=C(F)C(F)(F)F DMUPYMORYHFFCT-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DVMSVWIURPPRBC-UHFFFAOYSA-N 2,3,3-trifluoroprop-2-enoic acid Chemical class OC(=O)C(F)=C(F)F DVMSVWIURPPRBC-UHFFFAOYSA-N 0.000 description 1
- BOFUZZAQNVYZFF-UHFFFAOYSA-N 2-(3-chlorophenyl)-3-methylmorpholine Chemical compound CC1NCCOC1C1=CC=CC(Cl)=C1 BOFUZZAQNVYZFF-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- RXNYJUSEXLAVNQ-UHFFFAOYSA-N 4,4'-Dihydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1 RXNYJUSEXLAVNQ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- YWACAHLWCZJQBK-UHFFFAOYSA-N 4-[1,1-dichloro-1,3,3,3-tetrafluoro-2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound C1=CC(O)=CC=C1C(C(F)(Cl)Cl)(C(F)(F)F)C1=CC=C(O)C=C1 YWACAHLWCZJQBK-UHFFFAOYSA-N 0.000 description 1
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VKOUCJUTMGHNOR-UHFFFAOYSA-N Diphenolic acid Chemical compound C=1C=C(O)C=CC=1C(CCC(O)=O)(C)C1=CC=C(O)C=C1 VKOUCJUTMGHNOR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- BVMWIXWOIGJRGE-UHFFFAOYSA-N NP(O)=O Chemical class NP(O)=O BVMWIXWOIGJRGE-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- JBBHFHMVEOHFRE-UHFFFAOYSA-N anthracene-2,6-diol Chemical compound C1=C(O)C=CC2=CC3=CC(O)=CC=C3C=C21 JBBHFHMVEOHFRE-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- WXMZPPIDLJRXNK-UHFFFAOYSA-N butyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCC)C1=CC=CC=C1 WXMZPPIDLJRXNK-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZXKWUYWWVSKKQZ-UHFFFAOYSA-N cyclohexyl(diphenyl)phosphane Chemical compound C1CCCCC1P(C=1C=CC=CC=1)C1=CC=CC=C1 ZXKWUYWWVSKKQZ-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- VHBMRHILTSJCNR-UHFFFAOYSA-N diphenyl(tetradecyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCCCCCCCCC)C1=CC=CC=C1 VHBMRHILTSJCNR-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- KCYMAYAYGICFGX-UHFFFAOYSA-N dodecyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCCCCCCC)C1=CC=CC=C1 KCYMAYAYGICFGX-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- JFDOOIDOOQFNEI-UHFFFAOYSA-N hexadecyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(CCCCCCCCCCCCCCCC)C1=CC=CC=C1 JFDOOIDOOQFNEI-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 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
- 150000002500 ions Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- FZZQNEVOYIYFPF-UHFFFAOYSA-N naphthalene-1,6-diol Chemical compound OC1=CC=CC2=CC(O)=CC=C21 FZZQNEVOYIYFPF-UHFFFAOYSA-N 0.000 description 1
- ZUVBIBLYOCVYJU-UHFFFAOYSA-N naphthalene-1,7-diol Chemical compound C1=CC=C(O)C2=CC(O)=CC=C21 ZUVBIBLYOCVYJU-UHFFFAOYSA-N 0.000 description 1
- DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLAIWHIOIFKLEO-OWOJBTEDSA-N trans-stilbene-4,4'-diol Chemical compound C1=CC(O)=CC=C1\C=C\C1=CC=C(O)C=C1 XLAIWHIOIFKLEO-OWOJBTEDSA-N 0.000 description 1
- MDCWDBMBZLORER-UHFFFAOYSA-N triphenyl borate Chemical compound C=1C=CC=CC=1OB(OC=1C=CC=CC=1)OC1=CC=CC=C1 MDCWDBMBZLORER-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
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Industrial Application Field The present invention relates to a curable fluorine-containing elastomer vulcanized composition, and more specifically, a fluorine-containing elastomer vulcanized composition that has significantly improved compression set and excellent heat resistance, oil resistance, and chemical resistance. The present invention relates to a fluorine-containing elastomer vulcanizate composition that provides an elastomer vulcanizate and has excellent vulcanization properties, kneading processability, processing stability, storage stability, etc. Prior Art Highly fluorinated elastomer vulcanizates have excellent heat resistance, oil resistance, chemical resistance, etc., and are therefore used in various industrial fields, such as automobiles, ships, aircraft, hydraulics, and general machinery industries. It is widely used in fields such as pollution-related sectors as sealing materials such as O-rings and gaskets, diaphragms, hoses, rolls, and sheet materials. When a fluorinated elastomer vulcanizate is used for such purposes, it is necessary that the vulcanizate has particularly low compression set. Conventionally, vulcanization of fluorine-containing elastomers has been carried out using aliphatic diamines or organic peroxides as crosslinking agents. However, this method has poor scorch resistance (processing stability, storage stability), and the resulting vulcanizate has a large compression set, making it not necessarily suitable for the above-mentioned uses. . Therefore, it has been desired to develop a fluorine-containing elastomer vulcanizate composition that has both sufficient curing speed and scorch resistance, and can provide a vulcanizate with a small compression set. Recently, in order to meet these demands, a crosslinking method using a polyhydroxy compound with improved scorch resistance and compression set has been put into practical use. In this vulcanization system, as a vulcanization accelerator, for example, a quaternary phosphonium salt (Japanese Patent Publication No. 51-11138,
(Japanese Patent Publication No. 51-11655), quaternary ammonium salts (Japanese Patent Publication No. 49-17018, Japanese Patent Publication No. 52-38072, Japanese Patent Publication No. 57-20333), 8-alkyl (or aralkyl)-1, Quaternary ammonium salts of 8-diaza-bicyclo[5,4,0]-7-undecene (Japanese Patent Publication No. 52-8863), aminophosphinic acid derivatives (Japanese Patent Publication No. 58-17222), etc. are used. ing. However, even when these vulcanization systems are used, the compression set of the vulcanizate is low, especially at high temperatures.
It is also not at a fully satisfactory level. moreover,
During vulcanization molding, in order to manufacture molded products with particularly complex shapes or thick objects, reducing the vulcanization accelerator and slowing down the vulcanization rate can cause adhesion between the mold and the vulcanizate, resulting in defects. At the same time, the mold is contaminated. Furthermore, when quaternary ammonium salts are used, in addition to the above-mentioned disadvantages, they tend to absorb moisture and deliquesce significantly during storage, so special consideration is required for storage, which may not only cause problems in handling but also However, there are drawbacks such as deterioration of vulcanization properties and vulcanization physical properties. Problems to be Solved by the Invention The purpose of the present invention is to meet these demands, to have excellent vulcanization properties, kneading processability, processing stability, storage stability, etc., and to have a small compression set, and to be superior to conventional It is an object of the present invention to provide a fluorine-containing elastomer vulcanizate composition capable of producing a vulcanizate having excellent heat resistance, oil resistance, chemical resistance, etc., similar to the fluorine-containing elastomer vulcanizate. Means for Solving the Problems As a result of extensive research, the present inventors found that a compound having a specific phosphorus-nitrogen-phosphorus bond was used as a vulcanization accelerator, and a polyhydroxy compound and a divalent metal were used as a vulcanizing agent. It has been discovered that a composition using an oxide or a divalent metal hydroxide and blending these into a specific fluorine-containing elastomer copolymer can meet the above-mentioned purpose, and based on this knowledge, the present invention has been developed. We have finally completed the process. That is, the present invention provides (A) an elastomer copolymer having a vinylidene fluoride unit and at least one other fluorine-containing monomer unit; (B) a copolymer having the general formula [R 1 in the formula is an aryl group, or an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, -NR 3 2 ( However, R 3 has at least one substituent selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group, or a hydrogen atom), and a halogen atom. It is a substituted aryl group, R2 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and X is a halogen ion, hydroxide ion, or sulfate ion. , thiosulfate ion, nitrate ion, nitrite ion, acetate ion,
cyano ion, thiocyano ion, tetraphenylborate ion or perchlorate ion], (C) polyhydroxy compound and (D) divalent metal oxide or divalent metal hydroxide, or their The present invention provides a fluorine-containing elastomer vulcanized composition containing the mixture. Note that the electric charge of X in the general formula () is not limited to monovalent, but also includes multivalent ions based on the atom or atomic group of X. The elastomer copolymer used as component (A) in the vulcanized composition of the present invention has a vinylidene fluoride unit and at least one other fluorine-containing monomer unit, and the at least one Examples of other fluorine-containing monomer units include hexafluoropropene, 1,1,1,2,3-pentafluoropropene, 3,3,3-trifluoropropene, tetrafluoroethylene, trifluoroethylene, 1 , 2-difluoroethylene, dichlorodifluoroethylene, chlorotrifluoroethylene, hexafluorobutene, fluorinated vinyl ethers, fluorinated alkyl vinyl ethers,
Examples include perfluoroacrylic acid esters, and particularly important are hexafluoropropene, pentafluoropropene, and tetrafluoroethylene. Specific examples of the elastomer copolymer of component (A) include vinylidene fluoride-hexafluoropropene copolymer, vinylidene fluoride-hexafluoropropene-1,1,1,2,3-pentafluoropropene copolymer, and vinylidene fluoride-hexafluoropropene copolymer. Examples include polymers, vinylidene fluoride-hexafluoropropene-tetrafluoroethylene copolymers, and the like. Vulcanization of these copolymers is performed by converting the double bonds produced by a chemical dehydrofluorination reaction of hydrogen in molecules such as vinylidene fluoride units and pentafluoropropene units in the copolymers into crosslinking points. It is done as. The vulcanization accelerator used as component (B) in the vulcanization composition of the present invention is a compound represented by the general formula (), and specific examples thereof include bis(methyldiphenylphosphine) iminium tetra Phenylborate, bis(methyldiphenylphosphine)
iminium chloride, bis(butyldiphenylphosphine) iminium bromide, bis(dodecyldiphenylphosphine) iminium brolide, bis(tetradecyldiphenylphosphine) iminium chloride, bis(hexadecyl Diphenylphosphine) iminium chloride, bis(cyclohexyldiphenylphosphine) iminium chloride, bis(benzyldiphenylphosphine) iminium chloride, bis(benzyldiphenylphosphine) iminium acetate, bis [Benzyldi(4-methoxyphenyl)phosphine] iminium chloride, bis[benzyldi(4-fluorophenyl)phosphine] iminium chloride, bis[benzyldi(4-chlorophenyl)phosphine]
iminium chloride, bis[benzyl (4-
Bromophenyl)phosphine] iminium chloride, bis[benzyldi(4-cyanophenyl)phosphine] iminium chloride, bis[benzyldi(4-dimethylaminophenyl)phosphine] iminium chloride, bis[4-
Methylbenzyldi(4-methylphenyl)phosphine] iminium chloride, bis(2,4-
dimethylbenzyldiphenylphosphine) iminium chloride, bis(4-methoxybenzyldiphenylphosphine) iminium chloride, bis(4-chlorobenzyldiphenylphosphine) iminium chloride, bis(4-chlorobenzyl Diphenylphosphine) iminium chloride, bis(4-bromobenzyldiphenylphosphine) iminium chloride, and the like. Among these compounds, the typical component (B) is bis(benzyldiphenylphosphine) iminium chloride, which is classified as
und Allgemeine Hemie (Zeitschrift fur)
Anorganische und allgemeine Chemie), 492
Vol., pp. 122-134 (1984). As the polyhydroxy compound used as component (C) in the vulcanized composition of the present invention, at least one compound selected from polyhydroxy aromatic compounds and fluorine-containing polyhydroxy aliphatic compounds is preferably mentioned. Examples of polyhydroxy aromatic compounds include bisphenol A, bisphenol AF, resorcinol, 1,3,5-carbon trihydroxybenzene, 1,7-dihydroxynaphthalene, 2,7-dihydroxynaphthalene, 1,
6-dihydroxynaphthalene, 4,4'-dihydroxydiphenyl, 4,4'-dihydroxystilbene, 2,6-dihydroxyanthracene, hydroquinone, catechol, 2,2-bis(4-hydroxyphenyl)butane, 4,4 -Bis(4-hydroxyphenyl)valeric acid, 2,2-bis(4-
hydroxyphenyl)tetrafluorodichloropropane, 4,4'-dihydroxydiphenylsulfone, 4,4'-dihydroxydiphenylketone, tri(4-hydroxyphenyl)methane, 3,3',
5,5'-tetrachlorobisphenol A, 3,
3',5,5'-tetrabromobisphenol A and the like are used as fluorine-containing polyhydroxy aliphatic compounds, such as CF 2 (CF 2 CH 2 OH) 2 and HOCH 2
(CF 2 ) 4 OCF (CF 3 ) CH 2 OH, HOCH 2 (CF 2 ) 2 OCF
( CF3 ) CH2OH , CF2 ( CFHCF2CH2OH ) 2 ,
(CF 2 ) 3 (CF 2 CH 2 OH) 2 , (CF 2 ) 3
(CFHCF 2 CH 2 OH) 2 , (CF 2 ) 5 (CF 2 CH 2 OH) 2 ,
(CF 2 ) 5 (CFHCF 2 CH 2 OH) 2 and the like. Particularly preferred polyhydroxy compounds among these are bisphenol AF and hydroquinone, which may also be alkali metal salts or alkaline earth metal salts. These compounds may be used alone or in combination of two or more. Divalent metal oxides, divalent metal hydroxides, or mixtures thereof used as component (D) in the vulcanized composition of the present invention include, for example, magnesium, zinc,
Oxides or hydroxides of divalent metals such as calcium, lead, etc., or mixtures thereof, which may contain from 1 to 70% by weight of metal salts of weak acids. Examples of metal salts of this weak acid include stearates, benzoates, carbonates, oxalates, and phosphites of barium, sodium, potassium, lead, calcium, and the like. Regarding the blending ratio of each of the above-mentioned components in the vulcanized composition of the present invention, for 100 parts by weight of component (A),
Component (B) is 0.05 to 2.0 parts by weight, preferably 0.1 to 1.0 parts by weight, and component (C) is 0.1 to 10 parts by weight, preferably 0.6 to 1.0 parts by weight.
5.0 parts by weight and component (D) in an amount of 1 to 30 parts by weight, preferably 2 to 20 parts by weight. In the vulcanized composition of the present invention, if necessary,
Other ingredients, such as fillers and reinforcing agents such as carbon black, silica, clay, diatomaceous earth, and talc, plasticizers, and coloring agents, may be added as long as they do not depart from the gist of the present invention. , one or more conventionally known vulcanizing agents and accelerators may be blended. The vulcanized composition thus obtained is vulcanized according to a conventional method. This vulcanization method includes, for example, a method in which the mixture is kneaded in a roll-type rubber mill or a Banbury mixer, placed in a mold and pressurized for primary vulcanization, and then secondary vulcanization. Generally, the conditions for primary vulcanization are a temperature of 100 to 210°C, a time of 3 to 180 minutes, and a pressure of 20 to 100 kg/ cm2 , and the conditions for secondary vulcanization are a temperature of 150 to 300°C and a time of 0 to 30 minutes. A time range is used. In addition, other vulcanization methods include a method of preforming such as injection or extrusion, and then vulcanizing it;
Alternatively, a solution or dispersion is prepared using one or more of ketones such as methyl ethyl ketone, acetone, and cyclohexanone, and ethers such as methyl ethyl ether, diethyl ether, dioxane, and tetrahydrofuran. It is also possible to use a method of coating and vulcanizing the surface of a film, sheet, plate, tube, pipe, tank, large container, or other molded product. Effects of the Invention The fluorine-containing elastomer vulcanizate composition of the present invention is excellent in vulcanization properties, kneading processability, processing stability, storage stability, etc., and the fluorine-containing elastomer vulcanizate obtained therefrom is characterized by particularly low compression set, and also has excellent heat resistance, oil resistance, and chemical resistance, similar to fluorine-containing elastomer vulcanizates obtained using conventionally known vulcanizing agents. Thus, the vulcanized composition of the present invention has extremely high industrial value. EXAMPLES Next, the present invention will be explained in more detail with reference to Examples. Reference Example: Production of bis(benzyldiphenylphosphine) iminium chloride 3.15 mmol of [(C 6 H 5 ) 2 P] 2 NH was dissolved in 30 ml of benzene, and diluted with 10 ml of benzene.
Add 3.15 mmol of butyllithium-hexane solution and reflux while boiling for 1 hour. Then, after cooling to room temperature, 6.30 ml of benzyl chloride was added dropwise to form a white precipitate. The solvent is then distilled off and the residue is mixed with 35 ml of ethyl ether and refluxed while boiling. The white precipitate formed is filtered and washed twice with 15 ml of ethyl ether. Further dissolve in 15ml of ethanol and 10ml
of petroleum ether, white crystals of bis(benzyldiphenylphosphine) iminium chloride are formed. This is filtered and dried under vacuum (10 -3 torr) overnight. The yield of this stuff is 70%
The melting point was 255°C. Example 1 Vinylidene fluoride-hexafluoropropene-tetrafluoroethylene (67:
13:20 mol%) fluorine-containing elastomer copolymer
Wrap 100 parts by weight around two rolls, add 30 parts by weight of MT carbon black, 6 parts by weight of calcium hydroxide, magnesium oxide, (Kiyowa Mag #150)
After kneading 3 parts by weight of bisphenol AF, 2.0 parts by weight of bisphenol AF, and 0.55 parts by weight of bis(methyldiphenylphosphine) iminium tetraphenylborate, the mixture was left to mature overnight. After that, knead it again, put it into a mold, and heat it up.
Press vulcanization was performed at 177â for 10 minutes, and the sheet and o
-Each molded into a ring. Next, it was taken out from the mold and heated in an air circulation furnace at a temperature of 232°C for 24 hours to complete the secondary vulcanization. Note that Shore hardness (JIS-A), modulus, tensile strength, and elongation were all measured according to JIS K 6301. In addition, the compression set is determined by compressing an O-ring (inner diameter 23.7 mm, thickness 3.5 mm) by 25%.
Placed in the oven at 200â for 72 hours, ASTM D-396-61
It was measured according to method B of . Furthermore, the vulcanization test was conducted using a disk rheometer at 177â and the vibration frequency.
It was conducted under the conditions of 3 cpm and 3° amplitude. The vulcanization characteristics, mechanical properties, and compression set of the molded product thus obtained are shown in the table. Example 2 In the vulcanized composition of Example 1, 0.55 parts by weight of bis(methyldiphenylphosphine)iminium tetraphenylborate was replaced with bis(benzyldiphenylphosphine)iminium obtained in Reference Example. A vulcanized composition was prepared in the same manner as in Example 1, except that 0.45 parts by weight of chloride was used, and various tests were conducted. The results are shown in the table. Example 3 In the vulcanized composition of Example 1, in place of the fluorine-containing elastomer copolymer of Example 1, vinylidene fluoride having a Mooney viscosity of 36 (using a 121° C. ML rotor) obtained by emulsion polymerization was used. A vulcanized composition was prepared in the same manner as in Example 1, except that a fluorine-containing elastomer copolymer of hexafluoropropene (75:25 mol %) was used, and various tests were conducted.
The results are shown in the table. Example 4 In the vulcanized composition of Example 1, bis(benzyldiphenylphosphine)iminium acetate was substituted for 0.55 parts by weight of bis(methyldiphenylphosphine)iminium tetraphenylborate.
A vulcanized composition was prepared in the same manner as in Example 1, except that 0.45 parts by weight was used, and various tests were conducted. The results are shown in the table. Example 5 In the vulcanized composition of Example 1, bis(2,4-
Except for using 0.47 parts by weight of dimethylbenzyldiphenylphosphine) iminium chloride.
A vulcanized composition was prepared in the same manner as in Example 1, and various tests were conducted. The results are shown in the table. Example 6 In the vulcanized composition of Example 1, bis[benzyldi(4-methoxyphenyl)phosphine]iminium chloride was used instead of 0.55 parts by weight of bis(methyldiphenylphosphine)iminium tetraphenylborate. Except using 0.54 parts by weight,
A vulcanized composition was prepared in the same manner as in Example 1, and various tests were conducted. The results are shown in the table.
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Claims (1)
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ãããŒå ç¡«çµæç©ã[Scope of Claims] 1 (A) an elastomer copolymer having vinylidene fluoride units and at least one other fluorine-containing monomer unit, (B) general formula [R 1 in the formula is an aryl group, or an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a cyano group, -NR 3 2 ( However, R 3 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, an aryl group, or a hydrogen atom) and a halogen atom. It is an aryl group, R2 is an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and X is a halogen ion, hydroxide ion, sulfate ion, thiosulfate ion, nitrate ion, nitrite ion, acetate ion, cyano ion, thiocyano ion, tetraphenylborate ion or perchlorate ion], (C) polyhydroxy compound and (D) A fluorine-containing elastomer vulcanized composition comprising a valent metal oxide, a divalent metal hydroxide, or a mixture thereof.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59247578A JPS61126155A (en) | 1984-11-22 | 1984-11-22 | Vulcanizable fluoroelastomer composition |
CA000494004A CA1265288A (en) | 1984-11-22 | 1985-10-28 | Curable fluoroelastomer composition |
EP85114496A EP0182299B1 (en) | 1984-11-22 | 1985-11-14 | A curable fluoroelastomer composition |
DE8585114496T DE3582402D1 (en) | 1984-11-22 | 1985-11-14 | HAARDABLE FLUORELASTOMER COMPOSITION. |
KR1019850008753A KR900000971B1 (en) | 1984-11-22 | 1985-11-22 | Curable fluoroelastomer composition |
US07/060,995 US4748208A (en) | 1984-11-22 | 1987-06-05 | Curable elastomer composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP59247578A JPS61126155A (en) | 1984-11-22 | 1984-11-22 | Vulcanizable fluoroelastomer composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61126155A JPS61126155A (en) | 1986-06-13 |
JPS6362548B2 true JPS6362548B2 (en) | 1988-12-02 |
Family
ID=17165578
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP59247578A Granted JPS61126155A (en) | 1984-11-22 | 1984-11-22 | Vulcanizable fluoroelastomer composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS61126155A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20210024784A (en) | 2019-08-26 | 2021-03-08 | ëë ìŽì²šëšìì¬ ì£Œìíì¬ | Spinneret being able to form noncircular cross-sectional shape, yarn with noncircular cross-sectional shape manufactured using the same and method for manufacturing the same yarn |
-
1984
- 1984-11-22 JP JP59247578A patent/JPS61126155A/en active Granted
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20210024784A (en) | 2019-08-26 | 2021-03-08 | ëë ìŽì²šëšìì¬ ì£Œìíì¬ | Spinneret being able to form noncircular cross-sectional shape, yarn with noncircular cross-sectional shape manufactured using the same and method for manufacturing the same yarn |
Also Published As
Publication number | Publication date |
---|---|
JPS61126155A (en) | 1986-06-13 |
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