DE60212635T2 - Imidsalze als emulgatoren für die polymerisation von fluorolefinen - Google Patents
Imidsalze als emulgatoren für die polymerisation von fluorolefinen Download PDFInfo
- Publication number
- DE60212635T2 DE60212635T2 DE60212635T DE60212635T DE60212635T2 DE 60212635 T2 DE60212635 T2 DE 60212635T2 DE 60212635 T DE60212635 T DE 60212635T DE 60212635 T DE60212635 T DE 60212635T DE 60212635 T2 DE60212635 T2 DE 60212635T2
- Authority
- DE
- Germany
- Prior art keywords
- preparation
- fluoropolymers
- fluoropolymers according
- coc
- emulsifier
- 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 - Lifetime
Links
- 239000003995 emulsifying agent Substances 0.000 title claims abstract description 57
- 238000006116 polymerization reaction Methods 0.000 title abstract description 13
- -1 imide salts Chemical class 0.000 claims abstract description 27
- 229920002313 fluoropolymer Polymers 0.000 claims description 38
- 239000004811 fluoropolymer Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 20
- KZJUHXVCAHXJLR-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,4-nonafluoro-n-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)butane-1-sulfonamide Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F KZJUHXVCAHXJLR-UHFFFAOYSA-N 0.000 claims description 14
- 239000008346 aqueous phase Substances 0.000 claims description 12
- 150000001450 anions Chemical class 0.000 claims description 10
- 238000007720 emulsion polymerization reaction Methods 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000012986 chain transfer agent Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 230000002452 interceptive effect Effects 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- ZWWNWGPNBZIACR-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-1-(1,2,2-trifluoroethenoxy)-3-(trifluoromethoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)OC(F)(F)F ZWWNWGPNBZIACR-UHFFFAOYSA-N 0.000 claims description 2
- PGRNEGLBSNLPNP-UHFFFAOYSA-N 1,6-dichloro-3-methylhex-1-ene Chemical group ClC=CC(C)CCCCl PGRNEGLBSNLPNP-UHFFFAOYSA-N 0.000 claims description 2
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical compound FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 claims description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 claims description 2
- YTCHAEAIYHLXBK-UHFFFAOYSA-N 2-chloro-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Cl)C(F)(F)F YTCHAEAIYHLXBK-UHFFFAOYSA-N 0.000 claims description 2
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 claims description 2
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- IJDNGURDROLMKU-UHFFFAOYSA-N FC(C(C(F)(F)F)(C(C(C=C(F)F)(F)F)(F)F)F)(F)F Chemical group FC(C(C(F)(F)F)(C(C(C=C(F)F)(F)F)(F)F)F)(F)F IJDNGURDROLMKU-UHFFFAOYSA-N 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 17
- 239000002245 particle Substances 0.000 description 16
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 15
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 11
- YOALFLHFSFEMLP-UHFFFAOYSA-N azane;2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoic acid Chemical compound [NH4+].[O-]C(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YOALFLHFSFEMLP-UHFFFAOYSA-N 0.000 description 10
- 239000000839 emulsion Substances 0.000 description 10
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 239000004816 latex Substances 0.000 description 7
- 229920000126 latex Polymers 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 6
- 238000007334 copolymerization reaction Methods 0.000 description 6
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 6
- 238000010998 test method Methods 0.000 description 6
- UZBIRLJMURQVMX-UHFFFAOYSA-J tetrasodium;pyrene-1,3,6,8-tetrasulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].C1=C2C(S(=O)(=O)[O-])=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 UZBIRLJMURQVMX-UHFFFAOYSA-J 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 5
- 150000003949 imides Chemical class 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- 231100000693 bioaccumulation Toxicity 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000010924 continuous production Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000693 micelle Substances 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- LUYQYZLEHLTPBH-UHFFFAOYSA-N perfluorobutanesulfonyl fluoride Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(F)(=O)=O LUYQYZLEHLTPBH-UHFFFAOYSA-N 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229920001780 ECTFE Polymers 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- 239000004813 Perfluoroalkoxy alkane Substances 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000012935 ammoniumperoxodisulfate Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000007857 degradation product Substances 0.000 description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229920001973 fluoroelastomer Polymers 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000005065 mining Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920011301 perfluoro alkoxyl alkane Polymers 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002493 poly(chlorotrifluoroethylene) Polymers 0.000 description 2
- 239000005023 polychlorotrifluoroethylene (PCTFE) polymer Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 2
- 239000004810 polytetrafluoroethylene Substances 0.000 description 2
- 229920002620 polyvinyl fluoride Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000013049 sediment Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000004071 soot Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- 229910000792 Monel Inorganic materials 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 235000012545 Vaccinium macrocarpon Nutrition 0.000 description 1
- 235000002118 Vaccinium oxycoccus Nutrition 0.000 description 1
- 244000291414 Vaccinium oxycoccus Species 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- ABDBNWQRPYOPDF-UHFFFAOYSA-N carbonofluoridic acid Chemical class OC(F)=O ABDBNWQRPYOPDF-UHFFFAOYSA-N 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000004634 cranberry Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical compound C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 238000013023 gasketing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- ACFSQHQYDZIPRL-UHFFFAOYSA-N lithium;bis(1,1,2,2,2-pentafluoroethylsulfonyl)azanide Chemical compound [Li+].FC(F)(F)C(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)C(F)(F)F ACFSQHQYDZIPRL-UHFFFAOYSA-N 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000004812 organic fluorine compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000005007 perfluorooctyl group Chemical group FC(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)* 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001370 static light scattering Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 229920003249 vinylidene fluoride hexafluoropropylene elastomer Polymers 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004457 water analysis Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US896319 | 1997-07-17 | ||
| US09/896,319 US6545109B2 (en) | 2001-06-29 | 2001-06-29 | Imide salts as emulsifiers for the polymerization of fluoroolefins |
| PCT/US2002/010291 WO2003002622A1 (en) | 2001-06-29 | 2002-04-02 | Imide salts as emulsifiers for the polymerization of fluoroolefins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60212635D1 DE60212635D1 (de) | 2006-08-03 |
| DE60212635T2 true DE60212635T2 (de) | 2007-06-06 |
Family
ID=25406004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60212635T Expired - Lifetime DE60212635T2 (de) | 2001-06-29 | 2002-04-02 | Imidsalze als emulgatoren für die polymerisation von fluorolefinen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6545109B2 (https=) |
| EP (1) | EP1406936B1 (https=) |
| JP (1) | JP4080998B2 (https=) |
| AT (1) | ATE330977T1 (https=) |
| DE (1) | DE60212635T2 (https=) |
| WO (1) | WO2003002622A1 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6555510B2 (en) * | 2001-05-10 | 2003-04-29 | 3M Innovative Properties Company | Bis(perfluoroalkanesulfonyl)imides and their salts as surfactants/additives for applications having extreme environments and methods therefor |
| US7303852B2 (en) * | 2001-12-27 | 2007-12-04 | Shin-Etsu Chemical Co., Ltd. | Photoacid generating compounds, chemically amplified positive resist materials, and pattern forming method |
| JP4493393B2 (ja) * | 2004-04-23 | 2010-06-30 | 東京応化工業株式会社 | リソグラフィー用リンス液 |
| JP2008144206A (ja) * | 2006-12-07 | 2008-06-26 | Kobe Steel Ltd | チタンまたはチタン合金用酸洗液、およびこれを用いた酸洗方法 |
| US20100113691A1 (en) * | 2008-11-06 | 2010-05-06 | E. I. Du Pont De Nemours And Company | Fluoro olefin polymerization |
| EP2284200A1 (en) * | 2009-07-31 | 2011-02-16 | 3M Innovative Properties Company | Aqueous fluoropolymer dispersions containing a polyol comprising at least one long chain residue and method for producing them |
| US9969899B2 (en) | 2013-02-18 | 2018-05-15 | Honeywell International Inc. | Fluoropolymers containing a copolymerized fluoromonomer and a functional hydrocarbon comonomer and articles made from such fluoropolymers |
| JP7198207B2 (ja) * | 2017-09-01 | 2022-12-28 | 三菱マテリアル電子化成株式会社 | 界面活性剤 |
| KR102727961B1 (ko) | 2017-12-18 | 2024-11-08 | 보레알리스 아게 | 유리한 전기적 특성을 갖는 와이어 및 케이블 용도를 위한 중합체 블렌드 조성물 |
| US11506581B2 (en) | 2018-03-20 | 2022-11-22 | Agilent Technologies, Inc. | Mass spectrometry compatible salt formation for ionic liquid sample preparation |
| WO2020084854A1 (ja) | 2018-10-24 | 2020-04-30 | 三菱マテリアル電子化成株式会社 | 含フッ素イミド塩化合物及び界面活性剤 |
| EP3840075A1 (en) * | 2019-12-20 | 2021-06-23 | Novaled GmbH | Organic electronic device comprising a compound of formula (1), display device comprising the organic electronic device as well as compounds of formula (1) for use in organic electronic devices |
| EP4002508A1 (en) * | 2020-11-16 | 2022-05-25 | Novaled GmbH | Organic electronic device comprising a compound of formula (1), display device comprising the organic electronic device as well as compounds of formula (1) for use in organic electronic devices |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2701814A (en) | 1955-02-08 | Fluorocarbon compounds | ||
| DE3024450A1 (de) | 1980-06-28 | 1982-01-28 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von waessrigen, kolloidalen dispersionen von copolymerisaten des typs tetrafluorethylen-ethylen |
| US4558142A (en) | 1981-03-11 | 1985-12-10 | Hoffmann-La Roche Inc. | 7-Fluoro-prostacyclin analogs |
| FR2527602A1 (fr) | 1982-06-01 | 1983-12-02 | Anvar | Bis perhalogenoacyl- ou sulfonyl- imidures de metaux alcalins, leurs solutions solides avec des matieres plastiques et leur application a la constitution d'elements conducteurs pour des generateurs electrochimiques |
| US4529781A (en) | 1984-02-13 | 1985-07-16 | E. I. Du Pont De Nemours And Company | Process for the suspension polymerization of tetrafluoroethylene |
| US4555556A (en) | 1985-03-12 | 1985-11-26 | E. I. Du Pont De Nemours And Company | Tertiary perfluorinated compounds as rate enhancing additives in PTFE dispersion polymerization |
| FR2606217B1 (fr) | 1986-10-30 | 1990-12-14 | Elf Aquitaine | Nouveau materiau a conduction ionique constitue par un sel en solution dans un electrolyte liquide |
| US5256821A (en) | 1988-10-05 | 1993-10-26 | Societe Nationale Elf Aquitaine | Method of synthesis of sulphonylimides |
| FR2645533B1 (fr) | 1989-04-06 | 1991-07-12 | Centre Nat Rech Scient | Procede de synthese de sulfonylimidures |
| US5285002A (en) | 1993-03-23 | 1994-02-08 | Minnesota Mining And Manufacturing Company | Fluorine-containing polymers and preparation and use thereof |
| US5318674A (en) | 1993-06-30 | 1994-06-07 | Minnesota Mining And Manufacturing Company | Process for preparing perfluoroalkanesulfonyl fluorides |
| JP3117369B2 (ja) | 1994-09-12 | 2000-12-11 | セントラル硝子株式会社 | スルホンイミドの製造方法 |
| US5874616A (en) | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
| US5688884A (en) | 1995-08-31 | 1997-11-18 | E. I. Du Pont De Nemours And Company | Polymerization process |
| US6080487A (en) | 1996-08-26 | 2000-06-27 | 3M Innovative Properties Company | Method of improving adhesion between a fluoropolymer and a substrate |
| CA2187046A1 (fr) | 1996-10-03 | 1998-04-03 | Alain Vallee | Sulfonylimidures et sulfonylmethylures, leur utilisation comme photoinitiateur |
| US6013795A (en) | 1996-11-04 | 2000-01-11 | 3M Innovative Properties Company | Alpha-branched fluoroalkylcarbonyl fluorides and their derivatives |
| JP4823401B2 (ja) | 1996-12-30 | 2011-11-24 | イドロ―ケベック | 過フッ化アミド塩及びイオン伝導物質としてのその使用方法 |
| KR100559110B1 (ko) * | 1997-12-10 | 2006-03-13 | 미네소타 마이닝 앤드 매뉴팩춰링 캄파니 | 전기화학 시스템에서의 비스(퍼플루오로알킬설포닐)이미드 계면활성제 염 |
-
2001
- 2001-06-29 US US09/896,319 patent/US6545109B2/en not_active Expired - Lifetime
-
2002
- 2002-04-02 JP JP2003509001A patent/JP4080998B2/ja not_active Expired - Fee Related
- 2002-04-02 EP EP02780934A patent/EP1406936B1/en not_active Expired - Lifetime
- 2002-04-02 AT AT02780934T patent/ATE330977T1/de not_active IP Right Cessation
- 2002-04-02 WO PCT/US2002/010291 patent/WO2003002622A1/en not_active Ceased
- 2002-04-02 DE DE60212635T patent/DE60212635T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US6545109B2 (en) | 2003-04-08 |
| EP1406936A1 (en) | 2004-04-14 |
| ATE330977T1 (de) | 2006-07-15 |
| JP4080998B2 (ja) | 2008-04-23 |
| JP2004531632A (ja) | 2004-10-14 |
| EP1406936B1 (en) | 2006-06-21 |
| DE60212635D1 (de) | 2006-08-03 |
| US20030018149A1 (en) | 2003-01-23 |
| WO2003002622A1 (en) | 2003-01-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP5513514B2 (ja) | フルオロスルホネート | |
| EP2087017B1 (en) | Aqueous polymerization of fluorinated monomer using polymerization agent comprising fluoropolyether acid or salt and short chain fluorosurfactant | |
| EP2344448B1 (en) | Fluoroalkyl ether sulfonate surfactants | |
| DE60212635T2 (de) | Imidsalze als emulgatoren für die polymerisation von fluorolefinen | |
| JP2016537499A (ja) | フルオロモノマーの水性重合において核を形成するためのポリアルキレンオキシドの使用 | |
| WO2000018811A1 (de) | Verfahren zur herstellung eines schnellvernetzbaren fluorkautschukes | |
| HK1163053A (en) | Fluoroalkyl ether sulfonate surfactants |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |