JP4615804B2 - 有機オニウムおよびシュウ酸でブロックされた化合物を含むフルオロポリマー組成物 - Google Patents
有機オニウムおよびシュウ酸でブロックされた化合物を含むフルオロポリマー組成物 Download PDFInfo
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- JP4615804B2 JP4615804B2 JP2001530408A JP2001530408A JP4615804B2 JP 4615804 B2 JP4615804 B2 JP 4615804B2 JP 2001530408 A JP2001530408 A JP 2001530408A JP 2001530408 A JP2001530408 A JP 2001530408A JP 4615804 B2 JP4615804 B2 JP 4615804B2
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- Prior art keywords
- oxalate
- bisphenol
- group
- grams
- chloride
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 59
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 title claims description 36
- 150000001875 compounds Chemical class 0.000 title claims description 34
- 229920002313 fluoropolymer Polymers 0.000 title claims description 34
- 239000004811 fluoropolymer Substances 0.000 title claims description 34
- 235000006408 oxalic acid Nutrition 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- -1 alkyl oxalate Chemical compound 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 150000004010 onium ions Chemical class 0.000 claims description 12
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
- 239000003431 cross linking reagent Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000000178 monomer Substances 0.000 claims description 5
- 229910052755 nonmetal Inorganic materials 0.000 claims description 3
- 229920002959 polymer blend Polymers 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 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 33
- 229920001971 elastomer Polymers 0.000 description 29
- 239000005060 rubber Substances 0.000 description 24
- 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 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 239000004971 Cross linker Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000000370 acceptor Substances 0.000 description 9
- 229940106691 bisphenol a Drugs 0.000 description 9
- 239000000126 substance Substances 0.000 description 8
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 5
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- 229930185605 Bisphenol Natural products 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 238000000465 moulding Methods 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002015 acyclic group Chemical group 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000003901 oxalic acid esters Chemical group 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 2
- YVWNBNDYTKPZFP-UHFFFAOYSA-N 2-oxo-2-phenoxyacetic acid Chemical compound OC(=O)C(=O)OC1=CC=CC=C1 YVWNBNDYTKPZFP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000004703 alkoxides Chemical class 0.000 description 2
- 150000001449 anionic compounds Chemical class 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
- 229910052785 arsenic Inorganic materials 0.000 description 2
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 230000001588 bifunctional effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- ITHNIFCFNUZYLQ-UHFFFAOYSA-N dipropan-2-yl oxalate Chemical compound CC(C)OC(=O)C(=O)OC(C)C ITHNIFCFNUZYLQ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 229910001412 inorganic anion Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000002891 organic anions Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 235000013824 polyphenols Nutrition 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 238000010074 rubber mixing Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 2
- VERMEZLHWFHDLK-UHFFFAOYSA-N tetrahydroxybenzene Natural products OC1=CC=C(O)C(O)=C1O VERMEZLHWFHDLK-UHFFFAOYSA-N 0.000 description 2
- 229920003249 vinylidene fluoride hexafluoropropylene elastomer Polymers 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QYDODQJEOBYNCP-UHFFFAOYSA-N 1-[ethenoxy(difluoro)methyl]-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(C(F)(F)OC=C)C(F)=C1F QYDODQJEOBYNCP-UHFFFAOYSA-N 0.000 description 1
- VZUZVRUJXKDNSU-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-oxoacetic acid Chemical compound OC(=O)C(=O)OC1=CC=C(Cl)C=C1 VZUZVRUJXKDNSU-UHFFFAOYSA-N 0.000 description 1
- LGHDZIOWPVFVNB-UHFFFAOYSA-N 2-octoxy-2-oxoacetic acid Chemical compound CCCCCCCCOC(=O)C(O)=O LGHDZIOWPVFVNB-UHFFFAOYSA-N 0.000 description 1
- DMXBZAANBCMUMR-UHFFFAOYSA-N 2-oxo-2-propoxyacetic acid Chemical compound CCCOC(=O)C(O)=O DMXBZAANBCMUMR-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical class C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 description 1
- HMQONDPNQIFUQR-UHFFFAOYSA-N 4-[2-(2,3-difluoro-4-hydroxyphenyl)propan-2-yl]-2,3,5,6-tetrafluorophenol Chemical compound FC=1C(=C(C=CC1C(C)(C)C1=C(C(=C(C(=C1F)F)O)F)F)O)F HMQONDPNQIFUQR-UHFFFAOYSA-N 0.000 description 1
- YCQNMJFQVKKVNJ-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexa-2,4-dien-1-ylidene)propyl]phenol Chemical compound C1C=C(O)C=CC1=C(C)CC1=CC=C(O)C=C1 YCQNMJFQVKKVNJ-UHFFFAOYSA-N 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 0 CCCC*([P+](C)Cc1ccccc1)=C Chemical compound CCCC*([P+](C)Cc1ccccc1)=C 0.000 description 1
- WEIIEPKVWAGXEV-UHFFFAOYSA-L CCN(CC)[P+](CC1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)[P+](CC1=CC=CC=C1)(N(C)C)N(C)C.[Cl-].[Cl-].Cl Chemical compound CCN(CC)[P+](CC1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)[P+](CC1=CC=CC=C1)(N(C)C)N(C)C.[Cl-].[Cl-].Cl WEIIEPKVWAGXEV-UHFFFAOYSA-L 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- APDPVRQGFADMQI-UHFFFAOYSA-N FC1C(=C(C=CC1=C(CC1=C(C(=C(C(=C1F)F)O)F)F)C)O)F Chemical compound FC1C(=C(C=CC1=C(CC1=C(C(=C(C(=C1F)F)O)F)F)C)O)F APDPVRQGFADMQI-UHFFFAOYSA-N 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- BKXRKRANFLFTFU-UHFFFAOYSA-N bis(prop-2-enyl) oxalate Chemical compound C=CCOC(=O)C(=O)OCC=C BKXRKRANFLFTFU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
- 238000000748 compression moulding Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HZHMMLIMOUNKCK-UHFFFAOYSA-N dipropyl oxalate Chemical compound CCCOC(=O)C(=O)OCCC HZHMMLIMOUNKCK-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 206010016256 fatigue Diseases 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- UMKARVFXJJITLN-UHFFFAOYSA-N lead;phosphorous acid Chemical compound [Pb].OP(O)O UMKARVFXJJITLN-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- UHNWOJJPXCYKCG-UHFFFAOYSA-L magnesium oxalate Chemical compound [Mg+2].[O-]C(=O)C([O-])=O UHNWOJJPXCYKCG-UHFFFAOYSA-L 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000005460 perfluorocycloalkyl group Chemical group 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000006235 reinforcing carbon black Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- LMOSTVRARQCZIV-UHFFFAOYSA-N tributyl(2-carboxyethyl)phosphanium;chloride Chemical group [Cl-].CCCC[P+](CCCC)(CCCC)CCC(O)=O LMOSTVRARQCZIV-UHFFFAOYSA-N 0.000 description 1
- UDRBACREFJVZDG-UHFFFAOYSA-M tributyl(2-methoxypropyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC(C)OC UDRBACREFJVZDG-UHFFFAOYSA-M 0.000 description 1
- KSMYREBPTSSZDR-UHFFFAOYSA-M tributyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC=C KSMYREBPTSSZDR-UHFFFAOYSA-M 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/63—Halogen-containing esters of saturated acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/36—Oxalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/415,552 | 1999-10-08 | ||
| US09/415,552 US6359166B1 (en) | 1999-10-08 | 1999-10-08 | Oxalate ester blocked phenols |
| PCT/US2000/002454 WO2001027195A1 (en) | 1999-10-08 | 2000-02-01 | Fluoropolymer composition with organo-onium and blocked oxalate compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003511536A JP2003511536A (ja) | 2003-03-25 |
| JP2003511536A5 JP2003511536A5 (enExample) | 2007-03-22 |
| JP4615804B2 true JP4615804B2 (ja) | 2011-01-19 |
Family
ID=23646160
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001530408A Expired - Fee Related JP4615804B2 (ja) | 1999-10-08 | 2000-02-01 | 有機オニウムおよびシュウ酸でブロックされた化合物を含むフルオロポリマー組成物 |
Country Status (7)
| Country | Link |
|---|---|
| US (3) | US6359166B1 (enExample) |
| EP (2) | EP1512674B1 (enExample) |
| JP (1) | JP4615804B2 (enExample) |
| AU (1) | AU2748600A (enExample) |
| CA (1) | CA2384809A1 (enExample) |
| DE (2) | DE60016453T2 (enExample) |
| WO (1) | WO2001027195A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2003016756A2 (en) * | 2001-08-16 | 2003-02-27 | Parker Hannifin Corporation | Composite fuel permeation barrier seal |
| KR101452005B1 (ko) * | 2006-10-13 | 2014-10-21 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 모노-하이드록시 방향족 재료를 포함하는 분말 코팅 플루오로중합체 조성물 |
| WO2008103593A1 (en) * | 2007-02-19 | 2008-08-28 | 3M Innovative Properties Company | Powder coating fluoropolymer compositions with deprotectable aromatic materials |
| JP2024064170A (ja) * | 2022-10-27 | 2024-05-14 | ダイキン工業株式会社 | フッ素ゴム架橋用組成物および成形品 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA968100A (en) * | 1970-01-16 | 1975-05-20 | Eric Smith | Nylon foam - nylon skin panels and method therefore |
| GB1300722A (en) | 1970-01-16 | 1972-12-20 | Ici Ltd | Foamed polymeric materials |
| US3876654A (en) | 1970-12-23 | 1975-04-08 | Du Pont | Fluoroelastomer composition |
| US4177223A (en) * | 1977-12-27 | 1979-12-04 | E. I. Du Pont De Nemours And Company | Press-curable fluoropolymer compositions and process |
| US4233421A (en) | 1979-02-26 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition containing sulfonium curing agents |
| US4446216A (en) * | 1981-12-10 | 1984-05-01 | Smith Norman A | Photographic material |
| US5086123A (en) | 1984-02-27 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
| US4882390A (en) | 1988-04-01 | 1989-11-21 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| US4912171A (en) | 1988-04-01 | 1990-03-27 | Minnesota Mining And Manufacturing Company | Fluoroelastomer curing process with phosphonium compound |
| CA1328533C (en) * | 1988-04-01 | 1994-04-12 | Werner Marie Aschille Grootaert | Fluoroelastomer composition |
| US5262490A (en) | 1992-08-24 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
| JP3690813B2 (ja) | 1995-06-22 | 2005-08-31 | ダイネオン エルエルシー | 硬化性フルオロエラストマーの改良されたスコーチ安全性 |
| US5591804A (en) | 1995-12-21 | 1997-01-07 | Minnesota Mining And Manufacturing Company | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
| US5731453A (en) * | 1996-03-12 | 1998-03-24 | Ube Industries, Ltd. | Process for producing a diaryl carbonate |
| US5654375A (en) | 1996-05-24 | 1997-08-05 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing organo-onium compounds |
| JP2000516983A (ja) | 1996-08-26 | 2000-12-19 | ミネソタ マイニング アンド マニュファクチャリング カンパニー | フルオロポリマー―エポキシ樹脂半相互貫入網目構造組成物 |
| US5728773A (en) | 1997-02-21 | 1998-03-17 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium and blocked-carbonate compounds |
| IT1292361B1 (it) | 1997-05-20 | 1999-01-29 | Ausimont Spa | Composizioni fluoroelastomeriche volcanizzabili |
-
1999
- 1999-10-08 US US09/415,552 patent/US6359166B1/en not_active Expired - Lifetime
-
2000
- 2000-02-01 AU AU27486/00A patent/AU2748600A/en not_active Abandoned
- 2000-02-01 JP JP2001530408A patent/JP4615804B2/ja not_active Expired - Fee Related
- 2000-02-01 EP EP04027111A patent/EP1512674B1/en not_active Expired - Lifetime
- 2000-02-01 CA CA002384809A patent/CA2384809A1/en not_active Abandoned
- 2000-02-01 DE DE60016453T patent/DE60016453T2/de not_active Expired - Lifetime
- 2000-02-01 WO PCT/US2000/002454 patent/WO2001027195A1/en not_active Ceased
- 2000-02-01 EP EP00905879A patent/EP1235875B1/en not_active Expired - Lifetime
- 2000-02-01 DE DE60028426T patent/DE60028426T2/de not_active Expired - Lifetime
-
2001
- 2001-12-28 US US10/033,483 patent/US6566455B2/en not_active Expired - Lifetime
- 2001-12-28 US US10/033,485 patent/US6562911B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20020091282A1 (en) | 2002-07-11 |
| US6566455B2 (en) | 2003-05-20 |
| US20020099237A1 (en) | 2002-07-25 |
| AU2748600A (en) | 2001-04-23 |
| CA2384809A1 (en) | 2001-04-19 |
| US6359166B1 (en) | 2002-03-19 |
| EP1512674B1 (en) | 2006-05-31 |
| DE60016453D1 (de) | 2005-01-05 |
| DE60028426D1 (de) | 2006-07-06 |
| WO2001027195A1 (en) | 2001-04-19 |
| DE60016453T2 (de) | 2005-12-15 |
| EP1235875A1 (en) | 2002-09-04 |
| JP2003511536A (ja) | 2003-03-25 |
| DE60028426T2 (de) | 2007-05-24 |
| EP1512674A1 (en) | 2005-03-09 |
| EP1235875B1 (en) | 2004-12-01 |
| US6562911B2 (en) | 2003-05-13 |
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