CA1186100A - Obtention de polymeres de fluorocarbones et de vinyl-ethers - Google Patents

Obtention de polymeres de fluorocarbones et de vinyl-ethers

Info

Publication number: CA1186100A
Authority: CA; Canada
Prior art keywords: group; integer greater; radical; monomers; tetrafluoroethylene
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

CA000445211A

Other languages

English (en)

Inventor

William A. Mod

Bobby R. Ezzell

William P. Carl

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

1984-01-12

Publication date

1985-04-23

1981-06-10 Priority claimed from CA000379509A external-priority patent/CA1169439A/fr

1984-01-12 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1985-04-23 Application granted granted Critical

1985-04-23 Publication of CA1186100A publication Critical patent/CA1186100A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
229920000642 polymer Polymers 0.000 title description 19
229920002554 vinyl polymer Polymers 0.000 title 1
239000002253 acid Substances 0.000 claims abstract description 33
239000000178 monomer Substances 0.000 claims abstract description 32
229910052801 chlorine Inorganic materials 0.000 claims abstract description 30
-1 trifluoromonochloroethylene, trifluoroethylene Chemical group 0.000 claims abstract description 23
229910052794 bromium Inorganic materials 0.000 claims abstract description 22
239000000203 mixture Substances 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 18
229910052731 fluorine Inorganic materials 0.000 claims abstract description 15
238000006116 polymerization reaction Methods 0.000 claims abstract description 15
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 15
239000003999 initiator Substances 0.000 claims abstract description 10
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 claims abstract description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 4
239000005977 Ethylene Substances 0.000 claims abstract description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims abstract description 4
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims abstract description 4
PGOMVYSURVZIIW-UHFFFAOYSA-N trifluoro(nitroso)methane Chemical compound FC(F)(F)N=O PGOMVYSURVZIIW-UHFFFAOYSA-N 0.000 claims abstract description 4
DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 claims abstract description 3
150000003254 radicals Chemical class 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims description 3
229910000397 disodium phosphate Inorganic materials 0.000 claims description 3
235000019800 disodium phosphate Nutrition 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
229910002567 K2S2O8 Inorganic materials 0.000 claims 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims 2
235000019394 potassium persulphate Nutrition 0.000 claims 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims 2
150000002831 nitrogen free-radicals Chemical group 0.000 claims 1
239000000460 chlorine Substances 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 15
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 12
239000000543 intermediate Substances 0.000 description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
238000006114 decarboxylation reaction Methods 0.000 description 8
229960000834 vinyl ether Drugs 0.000 description 8
229910006095 SO2F Inorganic materials 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000001336 alkenes Chemical class 0.000 description 6
229910002092 carbon dioxide Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 5
229910005143 FSO2 Inorganic materials 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
239000003513 alkali Substances 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
235000011089 carbon dioxide Nutrition 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000002245 particle Substances 0.000 description 3
238000000197 pyrolysis Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000002002 slurry Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000001569 carbon dioxide Substances 0.000 description 2
238000007334 copolymerization reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
230000008014 freezing Effects 0.000 description 2
238000007710 freezing Methods 0.000 description 2
239000007789 gas Substances 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
150000002500 ions Chemical class 0.000 description 2
239000012528 membrane Substances 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen(.) Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
239000012048 reactive intermediate Substances 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
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
MIZLGWKEZAPEFJ-UHFFFAOYSA-N 1,1,2-trifluoroethene Chemical group FC=C(F)F MIZLGWKEZAPEFJ-UHFFFAOYSA-N 0.000 description 1
AOCMIZJYCVKCBZ-UHFFFAOYSA-N 2-[(butyldiazenyl)methyl]-4-methoxy-4-methylpentanenitrile Chemical compound CCCCN=NCC(C#N)CC(C)(C)OC AOCMIZJYCVKCBZ-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
HTHNTJCVPNKCPZ-UHFFFAOYSA-N 2-chloro-1,1-difluoroethene Chemical group FC(F)=CCl HTHNTJCVPNKCPZ-UHFFFAOYSA-N 0.000 description 1
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
241000518994 Conta Species 0.000 description 1
102000018361 Contactin Human genes 0.000 description 1
108060003955 Contactin Proteins 0.000 description 1
229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
241001163743 Perlodes Species 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
235000021028 berry Nutrition 0.000 description 1
239000003054 catalyst Substances 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
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000007720 emulsion polymerization reaction Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002222 fluorine compounds Chemical group 0.000 description 1
229920002313 fluoropolymer Polymers 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 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
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000002609 medium Substances 0.000 description 1
238000006263 metalation reaction Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 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
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 1
229910052939 potassium sulfate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical compound FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
229920001169 thermoplastic Polymers 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
238000004448 titration Methods 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000445211A 1980-06-11 1984-01-12 Obtention de polymeres de fluorocarbones et de vinyl-ethers Expired CA1186100A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US15853280A	1980-06-11	1980-06-11
US158,532		1980-06-11
CA000379509A CA1169439A (fr)	1980-06-11	1981-06-10	Methode de preparation de nouveaux ethers vinyliques de fluorocarbones, et polymeres ainsi obtenus

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000379509A Division CA1169439A (fr)	1980-06-11	1981-06-10	Methode de preparation de nouveaux ethers vinyliques de fluorocarbones, et polymeres ainsi obtenus

Publications (1)

Publication Number	Publication Date
CA1186100A true CA1186100A (fr)	1985-04-23

Family

ID=25669348

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000445211A Expired CA1186100A (fr)	1980-06-11	1984-01-12	Obtention de polymeres de fluorocarbones et de vinyl-ethers

Country Status (1)

Country	Link
CA (1)	CA1186100A (fr)

1984
- 1984-01-12 CA CA000445211A patent/CA1186100A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-04-23	MKEX	Expiry

Publication	Publication Date	Title
EP0041737B1 (fr)	1984-08-29	Procédé de préparation d'éthers fluorovinyliques et polymères résultants
CA1157045A (fr)	1983-11-15	Preparation de nouveaux ethers vinyliques
CA1187099A (fr)	1985-05-14	Preparation, decarboxylation et polymerisation de nouveaux fluorures d'acide, et monomeres ainsi obtenus
US4578512A (en)	1986-03-25	Process to produce novel fluorocarbon vinyl ethers and resulting polymers
US3882093A (en)	1975-05-06	Sulfonyl-containing fluorocarbon vinyl ethers and ion exchange membrane formed therefrom
US4138426A (en)	1979-02-06	Alkyl perfluoro-ω-fluoroformyl esters and monomers therefrom
US4687821A (en)	1987-08-18	Preparation, decarboxylation and polymerization of novel acid fluorides and resulting monomers
WO2012082546A1 (fr)	2012-06-21	Acides polysulfiniques partiellement fluorés et leurs sels
US4834922A (en)	1989-05-30	Process to produce novel fluorocarbon vinyl ethers and resulting polymers
CA1186100A (fr)	1985-04-23	Obtention de polymeres de fluorocarbones et de vinyl-ethers
US4804727A (en)	1989-02-14	Process to produce novel fluorocarbon vinyl ethers and resulting polymers
US4434273A (en)	1984-02-28	Perfluoroketovinyl ethers and copolymers therefrom
US3391119A (en)	1968-07-02	Nonconjugated perhalofluoro-beta-keto-omega-alkenses and their polymers
CN105431412A (zh)	2016-03-23	含-osf5基团的氟化的化合物及其制备方法
US4947006A (en)	1990-08-07	Process for preparing fluorinated conjugated olefinic products and new products thus obtained
JPH0254813B2 (fr)	1990-11-22
CA1259335A (fr)	1989-09-12	Preparation, decarboxylation et polymerisation de fluorures acides genre, et monomeres ainsi produits
JP3817757B2 (ja)	2006-09-06	新規ビニルエーテル化合物、その製造法およびその共重合体の製造法
US4225404A (en)	1980-09-30	Perfluoroolefin and perfluoroparaffin mixture and process for making same
CA1274650A (fr)	1990-09-25	Preparation, decarboxylation et polymerisation de nouveaux fluorures acides, et monomeres produits
US3739016A (en)	1973-06-12	Perfluoro-phenoxypropionic acid and esters and salts thereof
KR850000110B1 (ko)	1985-02-23	플루오로카본 비닐에테르의 중합방법
US4594458A (en)	1986-06-10	Vinyl ether monomers derived from alkyl perfluoro-ω-(2-iodoethoxy) compounds
JPH11335346A (ja)	1999-12-07	ペルフルオロアルキルビニルエーテル誘導体の製造方法
US4531011A (en)	1985-07-23	Alkyl perfluoro-omega-(2-iodoethoxy) compounds and vinyl ethers therefrom