CA1199034A - Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acyle; monomeres obtenus - Google Patents

Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acyle; monomeres obtenus

Info

Publication number: CA1199034A
Authority: CA; Canada
Prior art keywords: integer greater; formula; reaction; compound; temperature
Prior art date: 1980-06-11
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

Application number

CA000438464A

Other languages

English (en)

Inventor

Bobby R. Ezzell

William P. Carl

William A. Mod

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Dow Chemical Co

Original Assignee

Dow Chemical Co

Priority date (The priority date 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 date listed.)

1980-06-11

Filing date

1983-10-05

Publication date

1986-01-07

1980-06-11 Priority claimed from US06/158,426 external-priority patent/US4515989A/en

1983-10-05 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1986-01-07 Application granted granted Critical

1986-01-07 Publication of CA1199034A publication Critical patent/CA1199034A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title abstract description 25
150000002222 fluorine compounds Chemical class 0.000 title abstract description 6
239000000178 monomer Substances 0.000 title description 21
238000006116 polymerization reaction Methods 0.000 title description 9
238000006114 decarboxylation reaction Methods 0.000 title description 4
238000002360 preparation method Methods 0.000 title description 3
229910052801 chlorine Inorganic materials 0.000 claims abstract description 39
150000001875 compounds Chemical class 0.000 claims abstract description 29
229910052731 fluorine Inorganic materials 0.000 claims abstract description 28
229910052794 bromium Inorganic materials 0.000 claims abstract description 27
239000000203 mixture Substances 0.000 claims abstract description 20
229910052740 iodine Inorganic materials 0.000 claims abstract description 10
238000000034 method Methods 0.000 claims description 18
150000001768 cations Chemical class 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims 1
150000002576 ketones Chemical class 0.000 abstract description 3
238000006243 chemical reaction Methods 0.000 description 44
239000000460 chlorine Substances 0.000 description 37
-1 perfluoroalkyl iodides Chemical class 0.000 description 26
239000000047 product Substances 0.000 description 23
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 20
239000000543 intermediate Substances 0.000 description 20
229920000642 polymer Polymers 0.000 description 20
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 17
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 14
239000002904 solvent Substances 0.000 description 14
239000000463 material Substances 0.000 description 11
150000002118 epoxides Chemical class 0.000 description 10
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 9
150000001336 alkenes Chemical class 0.000 description 8
229910002092 carbon dioxide Inorganic materials 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
150000001265 acyl fluorides Chemical class 0.000 description 6
235000011089 carbon dioxide Nutrition 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
229920001577 copolymer Polymers 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
239000007789 gas Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
238000007334 copolymerization reaction Methods 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000376 reactant Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
JGZVUTYDEVUNMK-UHFFFAOYSA-N 5-carboxy-2',7'-dichlorofluorescein Chemical compound C12=CC(Cl)=C(O)C=C2OC2=CC(O)=C(Cl)C=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 JGZVUTYDEVUNMK-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
230000008030 elimination Effects 0.000 description 3
238000003379 elimination reaction Methods 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Chemical group 0.000 description 3
239000003999 initiator Substances 0.000 description 3
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
125000005010 perfluoroalkyl group Chemical group 0.000 description 3
238000000197 pyrolysis Methods 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000012190 activator Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
238000009835 boiling Methods 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical class FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
229920002313 fluoropolymer Polymers 0.000 description 2
239000004811 fluoropolymer Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
239000001257 hydrogen Chemical group 0.000 description 2
239000011630 iodine Substances 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
150000004812 organic fluorine compounds Chemical class 0.000 description 2
239000002245 particle Substances 0.000 description 2
229920005548 perfluoropolymer Polymers 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
230000000704 physical effect Effects 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910001220 stainless steel Inorganic materials 0.000 description 2
239000010935 stainless steel Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
FGUGXWGCSKSQFY-UHFFFAOYSA-N 1,1,1,2,2-pentafluoro-2-nitrosoethane Chemical compound FC(F)(F)C(F)(F)N=O FGUGXWGCSKSQFY-UHFFFAOYSA-N 0.000 description 1
QIROQPWSJUXOJC-UHFFFAOYSA-N 1,1,2,2,3,3,4,4,5,5,6-undecafluoro-6-(trifluoromethyl)cyclohexane Chemical compound FC(F)(F)C1(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F QIROQPWSJUXOJC-UHFFFAOYSA-N 0.000 description 1
TXGPGHBYAPBDAG-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-4,4-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C1(F)F TXGPGHBYAPBDAG-UHFFFAOYSA-N 0.000 description 1
IZLFSDDOEKWVLD-UHFFFAOYSA-N 2-chloro-1,1,3,4,4,5,6,6,6-nonafluorohex-1-ene Chemical compound FC(C(F)(F)F)C(C(C(=C(F)F)Cl)F)(F)F IZLFSDDOEKWVLD-UHFFFAOYSA-N 0.000 description 1
DDFHBQSCUXNBSA-UHFFFAOYSA-N 5-(5-carboxythiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)S1 DDFHBQSCUXNBSA-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
101150015684 FCF2 gene Proteins 0.000 description 1
229920002449 FKM Polymers 0.000 description 1
102000004457 Granulocyte-Macrophage Colony-Stimulating Factor Human genes 0.000 description 1
108010017213 Granulocyte-Macrophage Colony-Stimulating Factor Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [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
229910020656 PBr5 Inorganic materials 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000002730 additional effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
235000021028 berry Nutrition 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
229910021386 carbon form Inorganic materials 0.000 description 1
IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical class FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
230000001112 coagulating effect Effects 0.000 description 1
238000001246 colloidal dispersion Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
QDGONURINHVBEW-UHFFFAOYSA-N dichlorodifluoroethylene Chemical group FC(F)=C(Cl)Cl QDGONURINHVBEW-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
150000002484 inorganic compounds Chemical class 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000003014 ion exchange membrane Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000006263 metalation reaction Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 1
YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000012048 reactive intermediate Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
238000005979 thermal decomposition reaction Methods 0.000 description 1
PGOMVYSURVZIIW-UHFFFAOYSA-N trifluoro(nitroso)methane Chemical compound FC(F)(F)N=O PGOMVYSURVZIIW-UHFFFAOYSA-N 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
238000013022 venting Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000438464A 1980-06-11 1983-10-05 Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acyle; monomeres obtenus Expired CA1199034A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US158,426		1980-06-11
US06/158,426 US4515989A (en)	1980-06-11	1980-06-11	Preparation decarboxylation and polymerization of novel acid flourides and resulting monomers
CA000379491A CA1187099A (fr)	1980-06-11	1981-06-10	Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acide, et monomeres ainsi obtenus

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000379491A Division CA1187099A (fr)	1980-06-11	1981-06-10	Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acide, et monomeres ainsi obtenus

Publications (1)

Publication Number	Publication Date
CA1199034A true CA1199034A (fr)	1986-01-07

Family

ID=25669347

Family Applications (3)

Application Number	Title	Priority Date	Filing Date
CA000438464A Expired CA1199034A (fr)	1980-06-11	1983-10-05	Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acyle; monomeres obtenus
CA000455616A Expired CA1259335A (fr)	1980-06-11	1984-05-31	Preparation, decarboxylation et polymerisation de fluorures acides genre, et monomeres ainsi produits
CA000479654A Expired CA1259336A (fr)	1980-06-11	1985-04-19	Preparation, decarboxylation et polymerisation des fluorures acides genre, et momomeres ainsi produits

Family Applications After (2)

Application Number	Title	Priority Date	Filing Date
CA000455616A Expired CA1259335A (fr)	1980-06-11	1984-05-31	Preparation, decarboxylation et polymerisation de fluorures acides genre, et monomeres ainsi produits
CA000479654A Expired CA1259336A (fr)	1980-06-11	1985-04-19	Preparation, decarboxylation et polymerisation des fluorures acides genre, et momomeres ainsi produits

Country Status (1)

Country	Link
CA (3)	CA1199034A (fr)

1983
- 1983-10-05 CA CA000438464A patent/CA1199034A/fr not_active Expired
1984
- 1984-05-31 CA CA000455616A patent/CA1259335A/fr not_active Expired
1985
- 1985-04-19 CA CA000479654A patent/CA1259336A/fr not_active Expired

Also Published As

Publication number	Publication date
CA1259336A (fr)	1989-09-12
CA1259335A (fr)	1989-09-12

Legal Events

Date	Code	Title	Description
2003-01-07	MKEX	Expiry

Publication	Publication Date	Title
EP0072579B1 (fr)	1985-07-17	Préparation de fluorures d'acides fluorés
JP3856487B2 (ja)	2006-12-13	環状構造を有する弗素化ポリマー又はコポリマー
KR840000517B1 (ko)	1984-04-17	치환된 할로겐부위를 갖는 플루오로카본 에테르의 제조방법
GB1593222A (en)	1981-07-15	Perfluoroesters and their preparation
EP0041737B1 (fr)	1984-08-29	Procédé de préparation d'éthers fluorovinyliques et polymères résultants
EP0124378B1 (fr)	1988-08-10	Alkyléthers fluorés contenant de l'éthylène, leurs précurseurs et leurs copolymères avec du tétrafluoroéthylène
US4687821A (en)	1987-08-18	Preparation, decarboxylation and polymerization of novel acid fluorides and resulting monomers
US4578512A (en)	1986-03-25	Process to produce novel fluorocarbon vinyl ethers and resulting polymers
EP0937720B1 (fr)	2002-06-19	Perfluorodioxoles
EP0090498A2 (fr)	1983-10-05	Polyéthers fluorinés et dérivés
US20020183471A1 (en)	2002-12-05	New perfluorodioxoles
CA1199034A (fr)	1986-01-07	Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acyle; monomeres obtenus
US4474899A (en)	1984-10-02	Process for preparing ester fluorinated ion exchange polymer precursor by acid treatment of ether
US4675453A (en)	1987-06-23	Process and intermediates for fluorinated vinyl ether monomer
US4834922A (en)	1989-05-30	Process to produce novel fluorocarbon vinyl ethers and resulting polymers
US4556747A (en)	1985-12-03	Fluorinated vinyl ethers, copolymers thereof, and precursors thereto
CA1274650A (fr)	1990-09-25	Preparation, decarboxylation et polymerisation de nouveaux fluorures acides, et monomeres produits
EP0380129B1 (fr)	1993-12-08	Procédé de préparation de fluorures d'alpha-bromoacyles
US4804727A (en)	1989-02-14	Process to produce novel fluorocarbon vinyl ethers and resulting polymers
EP0050186B1 (fr)	1984-03-14	Méthode de préparation de composés vinyliques
US4590015A (en)	1986-05-20	Fluorinated polyether carboxylic acid fluorides
KR850000110B1 (ko)	1985-02-23	플루오로카본 비닐에테르의 중합방법
CA1144566A (fr)	1983-04-12	Esters d'alcoyle perfluoro-w-fluoroformyle, leur preparation et monomeres derives
EP0121330A1 (fr)	1984-10-10	Composés d'oméga 2-iodoéthoxy-perfluoroalcanes et éthers vinyliques à partir de ceux-ci