CA1179687A - Halogenures de ceto-3-glutaroyle fluores et polymeres derives - Google Patents

Halogenures de ceto-3-glutaroyle fluores et polymeres derives

Info

Publication number: CA1179687A
Authority: CA; Canada
Prior art keywords: fluoride; compounds; acid; copolymers; carbon atoms
Prior art date: 1979-11-16
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

CA000435393A

Other languages

English (en)

Inventor

David C. England

Edward G. Howard, Jr.

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and 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.)

1979-11-16

Filing date

1983-08-25

Publication date

1984-12-18

1979-11-16 Priority claimed from US06/095,071 external-priority patent/US4299949A/en

1983-08-25 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1983-08-25 Priority to CA000435393A priority Critical patent/CA1179687A/fr

1984-12-18 Application granted granted Critical

1984-12-18 Publication of CA1179687A publication Critical patent/CA1179687A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Chemical class 0.000 title abstract description 18
-1 3-ketoglutaroyl halides Chemical class 0.000 title abstract description 15
150000001875 compounds Chemical class 0.000 claims abstract description 15
238000000034 method Methods 0.000 claims abstract description 9
238000002360 preparation method Methods 0.000 claims abstract description 7
229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 20
NDNOUXQCMAHOSA-UHFFFAOYSA-N methyl 2,2,3,3-tetrafluoro-3-methoxypropanoate Chemical compound COC(=O)C(F)(F)C(F)(F)OC NDNOUXQCMAHOSA-UHFFFAOYSA-N 0.000 claims description 2
IXTJTMUIZVVXFD-UHFFFAOYSA-N 1,1,2,2,4,4,5,5-octafluoro-1,5-dimethoxypentan-3-one Chemical compound COC(F)(F)C(F)(F)C(=O)C(F)(F)C(F)(F)OC IXTJTMUIZVVXFD-UHFFFAOYSA-N 0.000 claims 2
ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 claims 1
229920001577 copolymer Polymers 0.000 abstract description 25
239000002253 acid Substances 0.000 abstract description 19
238000006243 chemical reaction Methods 0.000 abstract description 12
150000004820 halides Chemical group 0.000 abstract description 10
239000000178 monomer Substances 0.000 abstract description 6
125000004432 carbon atom Chemical group C* 0.000 description 16
239000000047 product Substances 0.000 description 15
150000002576 ketones Chemical class 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 8
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 8
NHJFHUKLZMQIHN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)F NHJFHUKLZMQIHN-UHFFFAOYSA-N 0.000 description 7
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
239000005977 Ethylene Substances 0.000 description 7
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 7
238000009835 boiling Methods 0.000 description 7
DTTSTUNIWPEOKC-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-3-oxopentanedioyl difluoride Chemical compound FC(=O)C(F)(F)C(=O)C(F)(F)C(F)=O DTTSTUNIWPEOKC-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
229910052783 alkali metal Inorganic materials 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
239000011701 zinc Substances 0.000 description 5
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
150000004703 alkoxides Chemical class 0.000 description 4
125000002877 alkyl aryl group Chemical group 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
ZJLRGBOOXHSDMQ-UHFFFAOYSA-N 2,2,4,4-tetrafluoro-3-oxopentanedioic acid Chemical compound OC(=O)C(F)(F)C(=O)C(F)(F)C(O)=O ZJLRGBOOXHSDMQ-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical group 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
238000002329 infrared spectrum Methods 0.000 description 3
239000003999 initiator Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
238000006136 alcoholysis reaction Methods 0.000 description 2
239000000908 ammonium hydroxide Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
150000005690 diesters Chemical class 0.000 description 2
238000004821 distillation Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 description 2
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
239000011253 protective coating Substances 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
125000005739 1,1,2,2-tetrafluoroethanediyl group Chemical group FC(F)([*:1])C(F)(F)[*:2] 0.000 description 1
BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 1
AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 1
238000004293 19F NMR spectroscopy Methods 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical compound OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 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
241000820057 Ithone Species 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
101000831256 Oryza sativa subsp. japonica Cysteine proteinase inhibitor 1 Proteins 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000003931 anilides Chemical class 0.000 description 1
229920005601 base polymer Polymers 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical group 0.000 description 1
150000001733 carboxylic acid esters Chemical group 0.000 description 1
238000009903 catalytic hydrogenation reaction 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
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
239000004020 conductor Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
238000005336 cracking Methods 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
PBWZKZYHONABLN-UHFFFAOYSA-M difluoroacetate Chemical compound [O-]C(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-M 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
150000002222 fluorine compounds Chemical class 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 1
238000007731 hot pressing Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000004812 organic fluorine compounds Chemical class 0.000 description 1
150000001451 organic peroxides Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
125000005010 perfluoroalkyl group Chemical group 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
125000001749 primary amide group Chemical group 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
KOPQZJAYZFAPBC-UHFFFAOYSA-N propanoyl propaneperoxoate Chemical compound CCC(=O)OOC(=O)CC KOPQZJAYZFAPBC-UHFFFAOYSA-N 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1

Landscapes

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

CA000435393A 1979-11-16 1983-08-25 Halogenures de ceto-3-glutaroyle fluores et polymeres derives Expired CA1179687A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000435393A CA1179687A (fr)	1979-11-16	1983-08-25	Halogenures de ceto-3-glutaroyle fluores et polymeres derives

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/095,071 US4299949A (en)	1979-11-16	1979-11-16	Fluorinated 3-ketoglutaroyl halides and polymers therefrom
US095,071		1979-11-16
CA000364624A CA1168264A (fr)	1979-11-16	1980-11-13	Halogenures fluores de 3-cetoglutaroyle et polymere ainsi obtenus
CA000435393A CA1179687A (fr)	1979-11-16	1983-08-25	Halogenures de ceto-3-glutaroyle fluores et polymeres derives

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000364624A Division CA1168264A (fr)	1979-11-16	1980-11-13	Halogenures fluores de 3-cetoglutaroyle et polymere ainsi obtenus

Publications (1)

Publication Number	Publication Date
CA1179687A true CA1179687A (fr)	1984-12-18

Family

ID=27166884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000435393A Expired CA1179687A (fr)	1979-11-16	1983-08-25	Halogenures de ceto-3-glutaroyle fluores et polymeres derives

Country Status (1)

Country	Link
CA (1)	CA1179687A (fr)

1983
- 1983-08-25 CA CA000435393A patent/CA1179687A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-12-18	MKEX	Expiry

Publication	Publication Date	Title
US4138426A (en)	1979-02-06	Alkyl perfluoro-ω-fluoroformyl esters and monomers therefrom
DE69808241T2 (de)	2003-08-07	Mit fluorverbindungen aufgepfropften polymerisaten
DE69704815T2 (de)	2001-10-25	Wasserstoff enthaltende Fluorosurfactant und seine Verwendung in der Polymerisation
US3814741A (en)	1974-06-04	Acrylic and methacrylic monomers,polymers and copolymers thereof
US4948844A (en)	1990-08-14	Process for preparation of perfluorinated copolymer
EP0868447B1 (fr)	2000-02-23	Iodonitriles utilises comme agents de migration de chaine dans la fabrication de perfluoropolymeres
CA1169439A (fr)	1984-06-19	Methode de preparation de nouveaux ethers vinyliques de fluorocarbones, et polymeres ainsi obtenus
EP0062120B1 (fr)	1985-07-24	Perfluoro (2-méthyl-5-oxo-3-oxa-hexanoates) d'alcoyle et leurs dérivés
JPH10502676A (ja)	1998-03-10	ビニルモノマー類の重合およびテロメリゼーションで用いるに適した炭素を基とする開始剤
DE69202764T2 (de)	1995-11-23	Perfluorierte cyclische polyether, verwendbar als schmiermittel und wärmeübertragungsflüssigkeiten.
CA1179687A (fr)	1984-12-18	Halogenures de ceto-3-glutaroyle fluores et polymeres derives
US2667469A (en)	1954-01-26	Vinyl esters of hydrocarbonsulfonic acids and polymers thereof
JPH10237130A (ja)	1998-09-08	含フッ素ニトリルおよびその重合体
CA2659497C (fr)	2012-01-17	Fluorure d'acide polyfluoroalcanecarboxylique, procede pour sa production et procede de production d'acide polyfluoroalcanecarboxylique au moyen de celui-ci
CA1168264A (fr)	1984-05-29	Halogenures fluores de 3-cetoglutaroyle et polymere ainsi obtenus
US4581430A (en)	1986-04-08	Acrylate and methacrylate polymers and processes for preparing them
US5847048A (en)	1998-12-08	Polymers containing fluoroalkoxy side chains
US4608206A (en)	1986-08-26	Fluorinated 3-ketoglutaroyl halides
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