CA1247291A - Copolymere reticulable a teneur de fluor - Google Patents

Copolymere reticulable a teneur de fluor

Info

Publication number: CA1247291A
Authority: CA; Canada
Prior art keywords: copolymer; fluorine; mole; sulfonyl chloride; chloride group
Prior art date: 1986-02-24
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

CA000502559A

Other languages

English (en)

Inventor

Tetsuro Ohta

Masato Hamada

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.)

Asahi Kasei Corp

Original Assignee

Asahi Kasei Kogyo KK

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.)

1986-02-24

Filing date

1986-02-24

Publication date

1988-12-20

1986-02-24 Application filed by Asahi Kasei Kogyo KK filed Critical Asahi Kasei Kogyo KK

1986-02-24 Priority to CA000502559A priority Critical patent/CA1247291A/fr

1988-12-20 Application granted granted Critical

1988-12-20 Publication of CA1247291A publication Critical patent/CA1247291A/fr

Status Expired legal-status Critical Current

Links

229920001577 copolymer Polymers 0.000 title claims abstract description 122
229910052731 fluorine Inorganic materials 0.000 title claims abstract description 54
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims abstract description 50
239000011737 fluorine Substances 0.000 title claims abstract description 50
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical group ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims abstract description 51
239000000178 monomer Substances 0.000 claims abstract description 42
150000001875 compounds Chemical class 0.000 claims abstract description 32
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 12
BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 9
HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 9
229920001971 elastomer Polymers 0.000 abstract description 14
239000000806 elastomer Substances 0.000 abstract description 13
239000000126 substance Substances 0.000 abstract description 8
238000006116 polymerization reaction Methods 0.000 description 25
238000004132 cross linking Methods 0.000 description 14
238000000034 method Methods 0.000 description 14
239000000203 mixture Substances 0.000 description 13
238000001723 curing Methods 0.000 description 12
239000007787 solid Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
239000000470 constituent Substances 0.000 description 9
238000010521 absorption reaction Methods 0.000 description 8
239000003999 initiator Substances 0.000 description 8
150000001451 organic peroxides Chemical class 0.000 description 8
229920000642 polymer Polymers 0.000 description 8
238000004458 analytical method Methods 0.000 description 7
230000006835 compression Effects 0.000 description 7
238000007906 compression Methods 0.000 description 7
238000003756 stirring Methods 0.000 description 7
AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000007334 copolymerization reaction Methods 0.000 description 6
239000007789 gas Substances 0.000 description 6
150000003254 radicals Chemical class 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
230000000052 comparative effect Effects 0.000 description 5
239000003431 cross linking reagent Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
-1 ethylene, propylene, pentafluoropropylene Chemical group 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
239000003014 ion exchange membrane Substances 0.000 description 4
150000002978 peroxides Chemical class 0.000 description 4
OVGRCEFMXPHEBL-UHFFFAOYSA-N 1-ethenoxypropane Chemical compound CCCOC=C OVGRCEFMXPHEBL-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000003708 ampul Substances 0.000 description 3
238000007385 chemical modification Methods 0.000 description 3
230000003247 decreasing effect Effects 0.000 description 3
229910001873 dinitrogen Inorganic materials 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000010556 emulsion polymerization method Methods 0.000 description 3
125000001153 fluoro group Chemical group F* 0.000 description 3
238000010528 free radical solution polymerization reaction Methods 0.000 description 3
239000011521 glass Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
229920003023 plastic Polymers 0.000 description 3
239000004033 plastic Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
229910001220 stainless steel Inorganic materials 0.000 description 3
239000010935 stainless steel Substances 0.000 description 3
238000010558 suspension polymerization method Methods 0.000 description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
208000036366 Sensation of pressure Diseases 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
239000000654 additive Substances 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
238000003912 environmental pollution Methods 0.000 description 2
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
KHXKESCWFMPTFT-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane Chemical compound FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F KHXKESCWFMPTFT-UHFFFAOYSA-N 0.000 description 1
XQWJXSCYGRKTKW-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-(1,2,2-trifluoroethenoxy)propane;1,1,2,2-tetrafluoroethene Chemical compound FC(F)=C(F)F.FC(F)=C(F)OC(F)(F)C(F)(F)C(F)(F)F XQWJXSCYGRKTKW-UHFFFAOYSA-N 0.000 description 1
UJPMYEOUBPIPHQ-UHFFFAOYSA-N 1,1,1-trifluoroethane Chemical compound CC(F)(F)F UJPMYEOUBPIPHQ-UHFFFAOYSA-N 0.000 description 1
DOWJGHMZJRTBBD-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethene;1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)F.FC(F)=C(F)OC(F)(F)F DOWJGHMZJRTBBD-UHFFFAOYSA-N 0.000 description 1
NALFRYPTRXKZPN-UHFFFAOYSA-N 1,1-bis(tert-butylperoxy)-3,3,5-trimethylcyclohexane Chemical compound CC1CC(C)(C)CC(OOC(C)(C)C)(OOC(C)(C)C)C1 NALFRYPTRXKZPN-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
JUTIIYKOQPDNEV-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanoyl 2,2,3,3,4,4,4-heptafluorobutaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)C(F)(F)F JUTIIYKOQPDNEV-UHFFFAOYSA-N 0.000 description 1
LXANZHXWGZWFAC-UHFFFAOYSA-N 2,3-dichloro-1,1,1,2,3,4,4,4-octafluorobutane Chemical compound FC(F)(F)C(F)(Cl)C(F)(Cl)C(F)(F)F LXANZHXWGZWFAC-UHFFFAOYSA-N 0.000 description 1
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
239000004342 Benzoyl peroxide Substances 0.000 description 1
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
102100024133 Coiled-coil domain-containing protein 50 Human genes 0.000 description 1
229920008712 Copo Polymers 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
NCHFSZWJHFHNCJ-UHFFFAOYSA-N FC(=C(C(C(C(F)(F)F)(OC(C(C(S(=O)(=O)Cl)(F)F)(F)F)(F)F)F)(F)F)F)OC(=C(F)C(C(C(F)(F)F)(F)OC(C(C(F)(F)S(=O)(=O)Cl)(F)F)(F)F)(F)F)F Chemical compound FC(=C(C(C(C(F)(F)F)(OC(C(C(S(=O)(=O)Cl)(F)F)(F)F)(F)F)F)(F)F)F)OC(=C(F)C(C(C(F)(F)F)(F)OC(C(C(F)(F)S(=O)(=O)Cl)(F)F)(F)F)(F)F)F NCHFSZWJHFHNCJ-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
101000910772 Homo sapiens Coiled-coil domain-containing protein 50 Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
238000009835 boiling Methods 0.000 description 1
238000012662 bulk polymerization Methods 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000012159 carrier gas Substances 0.000 description 1
239000012986 chain transfer agent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 1
238000005336 cracking Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
229940052308 general anesthetics halogenated hydrocarbons Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000004898 kneading Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 description 1
235000019407 octafluorocyclobutane Nutrition 0.000 description 1
230000009965 odorless effect Effects 0.000 description 1
YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
238000011417 postcuring Methods 0.000 description 1
239000002243 precursor Substances 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
230000002285 radioactive effect Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000000926 separation method Methods 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
KJWHEZXBZQXVSA-UHFFFAOYSA-N tris(prop-2-enyl) phosphite Chemical compound C=CCOP(OCC=C)OCC=C KJWHEZXBZQXVSA-UHFFFAOYSA-N 0.000 description 1

Landscapes

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

CA000502559A 1986-02-24 1986-02-24 Copolymere reticulable a teneur de fluor Expired CA1247291A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000502559A CA1247291A (fr)	1986-02-24	1986-02-24	Copolymere reticulable a teneur de fluor

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000502559A CA1247291A (fr)	1986-02-24	1986-02-24	Copolymere reticulable a teneur de fluor

Publications (1)

Publication Number	Publication Date
CA1247291A true CA1247291A (fr)	1988-12-20

Family

ID=4132538

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000502559A Expired CA1247291A (fr)	1986-02-24	1986-02-24	Copolymere reticulable a teneur de fluor

Country Status (1)

Country	Link
CA (1)	CA1247291A (fr)

1986
- 1986-02-24 CA CA000502559A patent/CA1247291A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2006-02-24	MKEX	Expiry

Publication	Publication Date	Title
EP0407937B1 (fr)	1994-10-12	Elastomères fluorées ayant une transformabilité améliorée et leur procédé de préparation
EP0475959B1 (fr)	1994-11-02	Perfluoropolymeres contenant un groupement cyano et ayant des sites de reticulation iode
RU2136702C1 (ru)	1999-09-10	Фторэластомер
EP0446725B1 (fr)	1996-01-17	Fluoro-élastomères résistant à la base ayant une transformabilité et curabilité améliorée
EP0472653B1 (fr)	1994-11-02	Preparation de cyano perfluoropolymeres contenant des sites de durcissement iodiques
EP0398241B1 (fr)	1993-12-29	Elastomères fluorés durcissables par des peroxydes comprenant des sites de réticulation bromés et iodés et leur préparation
EP0425259B1 (fr)	1993-09-22	Fluoro-élastomères et chlorofluoro-élastomères durcissables à l'aide de peroxydes contenant le brome ou l'iode comme sites de vulcanisation et procédé pour leur préparation
RU2131888C1 (ru)	1999-06-20	Фторсодержащие полимеры и способ их получения
EP0472620B1 (fr)	1994-11-02	Perfluoropolymeres contenant un groupement bromo et ayant des sites de reticulation iode
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