JP6702929B2 - 低粘性を特徴とする耐酸素プラズマ組成物およびそれに関連する方法 - Google Patents
低粘性を特徴とする耐酸素プラズマ組成物およびそれに関連する方法 Download PDFInfo
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- JP6702929B2 JP6702929B2 JP2017246300A JP2017246300A JP6702929B2 JP 6702929 B2 JP6702929 B2 JP 6702929B2 JP 2017246300 A JP2017246300 A JP 2017246300A JP 2017246300 A JP2017246300 A JP 2017246300A JP 6702929 B2 JP6702929 B2 JP 6702929B2
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- 239000000203 mixture Substances 0.000 title claims description 80
- 238000000034 method Methods 0.000 title claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 title claims description 14
- 239000001301 oxygen Substances 0.000 title claims description 14
- 229910052760 oxygen Inorganic materials 0.000 title claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- -1 perfluoro Chemical group 0.000 claims description 45
- 239000000178 monomer Substances 0.000 claims description 44
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 42
- 229920006169 Perfluoroelastomer Polymers 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 28
- 235000010290 biphenyl Nutrition 0.000 claims description 26
- 239000004305 biphenyl Substances 0.000 claims description 26
- 125000003277 amino group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 21
- 229920002313 fluoropolymer Polymers 0.000 claims description 21
- 239000004811 fluoropolymer Substances 0.000 claims description 21
- 239000003086 colorant Substances 0.000 claims description 20
- 229920001973 fluoroelastomer Polymers 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 16
- 150000002430 hydrocarbons Chemical group 0.000 claims description 16
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 14
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 12
- 239000010702 perfluoropolyether Substances 0.000 claims description 12
- HYMJOTOLJAHZCH-UHFFFAOYSA-N 2,2,3,3,4,4,4-heptafluorobutanimidamide Chemical group NC(=N)C(F)(F)C(F)(F)C(F)(F)F HYMJOTOLJAHZCH-UHFFFAOYSA-N 0.000 claims description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 9
- 235000019239 indanthrene blue RS Nutrition 0.000 claims description 7
- UHOKSCJSTAHBSO-UHFFFAOYSA-N indanthrone blue Chemical compound C1=CC=C2C(=O)C3=CC=C4NC5=C6C(=O)C7=CC=CC=C7C(=O)C6=CC=C5NC4=C3C(=O)C2=C1 UHOKSCJSTAHBSO-UHFFFAOYSA-N 0.000 claims description 7
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 7
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 7
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 6
- 229920001343 polytetrafluoroethylene Polymers 0.000 claims description 6
- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 4
- 230000001747 exhibiting effect Effects 0.000 claims description 4
- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical compound C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 14
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims 2
- 238000001723 curing Methods 0.000 description 61
- 125000004093 cyano group Chemical group *C#N 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 19
- 229920005548 perfluoropolymer Polymers 0.000 description 17
- 150000001721 carbon Chemical group 0.000 description 14
- 150000005215 alkyl ethers Chemical class 0.000 description 13
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 8
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 125000000524 functional group Chemical group 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 239000006254 rheological additive Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920001774 Perfluoroether Chemical group 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- DIRTUSMKNXOPBJ-UHFFFAOYSA-N carbamic acid;propane-1,3-diamine Chemical compound NC(O)=O.NCCCN DIRTUSMKNXOPBJ-UHFFFAOYSA-N 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 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
- 150000004679 hydroxides Chemical class 0.000 description 2
- DZCCLNYLUGNUKQ-UHFFFAOYSA-N n-(4-nitrosophenyl)hydroxylamine Chemical compound ONC1=CC=C(N=O)C=C1 DZCCLNYLUGNUKQ-UHFFFAOYSA-N 0.000 description 2
- VKWNTWQXVLKCSG-UHFFFAOYSA-N n-ethyl-1-[(4-phenyldiazenylphenyl)diazenyl]naphthalen-2-amine Chemical compound CCNC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 VKWNTWQXVLKCSG-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- JJZONEUCDUQVGR-VCFJNTAESA-N (NE)-N-[(2Z)-2-hydroxyimino-1,2-diphenylethylidene]hydroxylamine Chemical compound O\N=C(\C(=N/O)\C1=CC=CC=C1)/C1=CC=CC=C1 JJZONEUCDUQVGR-VCFJNTAESA-N 0.000 description 1
- 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
- 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
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- JMGNVALALWCTLC-UHFFFAOYSA-N 1-fluoro-2-(2-fluoroethenoxy)ethene Chemical compound FC=COC=CF JMGNVALALWCTLC-UHFFFAOYSA-N 0.000 description 1
- VHJKOLAKAFYZMC-UHFFFAOYSA-N 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanimidamide Chemical compound NC(=N)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F VHJKOLAKAFYZMC-UHFFFAOYSA-N 0.000 description 1
- XSQHUYDRSDBCHN-UHFFFAOYSA-N 2,3-dimethyl-2-propan-2-ylbutanenitrile Chemical compound CC(C)C(C)(C#N)C(C)C XSQHUYDRSDBCHN-UHFFFAOYSA-N 0.000 description 1
- CPDIMKQNIGAJOG-UHFFFAOYSA-N 2-(cinnamylideneamino)ethanamine Chemical compound NCCN=CC=CC1=CC=CC=C1 CPDIMKQNIGAJOG-UHFFFAOYSA-N 0.000 description 1
- IAFBRPFISOTXSO-UHFFFAOYSA-N 2-[[2-chloro-4-[3-chloro-4-[[1-(2,4-dimethylanilino)-1,3-dioxobutan-2-yl]diazenyl]phenyl]phenyl]diazenyl]-n-(2,4-dimethylphenyl)-3-oxobutanamide Chemical compound C=1C=C(C)C=C(C)C=1NC(=O)C(C(=O)C)N=NC(C(=C1)Cl)=CC=C1C(C=C1Cl)=CC=C1N=NC(C(C)=O)C(=O)NC1=CC=C(C)C=C1C IAFBRPFISOTXSO-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical group NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- AUUGWBRHHCJWHN-UHFFFAOYSA-N 3-(cinnamylideneamino)propan-1-amine Chemical compound NCCCN=CC=CC1=CC=CC=C1 AUUGWBRHHCJWHN-UHFFFAOYSA-N 0.000 description 1
- LISYJIIYAKKNFI-UHFFFAOYSA-N 6-(cinnamylideneamino)hexan-1-amine Chemical compound NCCCCCCN=CC=CC1=CC=CC=C1 LISYJIIYAKKNFI-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZJNQYVGWFPCKMJ-UHFFFAOYSA-N C(N)(O)=O.NC1CCC(CC1)C Chemical compound C(N)(O)=O.NC1CCC(CC1)C ZJNQYVGWFPCKMJ-UHFFFAOYSA-N 0.000 description 1
- NNQLCSNXVLMPOX-UHFFFAOYSA-N C1=CC=C2C(=NO)C=CC(=NO)C2=C1 Chemical compound C1=CC=C2C(=NO)C=CC(=NO)C2=C1 NNQLCSNXVLMPOX-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 229920002449 FKM Polymers 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- ZTWQZJLUUZHJGS-UHFFFAOYSA-N Vat Yellow 4 Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C4=CC=CC=C4C(=O)C4=C3C2=C1C=C4 ZTWQZJLUUZHJGS-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000001000 anthraquinone dye Chemical class 0.000 description 1
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Chemical group 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KWLMIXQRALPRBC-UHFFFAOYSA-L hectorite Chemical compound [Li+].[OH-].[OH-].[Na+].[Mg+2].O1[Si]2([O-])O[Si]1([O-])O[Si]([O-])(O1)O[Si]1([O-])O2 KWLMIXQRALPRBC-UHFFFAOYSA-L 0.000 description 1
- 229910000271 hectorite Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- RLRHPCKWSXWKBG-UHFFFAOYSA-N n-(2-azaniumylethyl)carbamate Chemical compound NCCNC(O)=O RLRHPCKWSXWKBG-UHFFFAOYSA-N 0.000 description 1
- ATPFMBHTMKBVLS-UHFFFAOYSA-N n-[6-(cinnamylideneamino)hexyl]-3-phenylprop-2-en-1-imine Chemical compound C=1C=CC=CC=1C=CC=NCCCCCCN=CC=CC1=CC=CC=C1 ATPFMBHTMKBVLS-UHFFFAOYSA-N 0.000 description 1
- 239000002071 nanotube Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000001048 orange dye Substances 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/29—Compounds containing one or more carbon-to-nitrogen double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/32—Compounds containing nitrogen bound to oxygen
- C08K5/33—Oximes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L27/00—Compositions of homopolymers or 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; Compositions of derivatives of such polymers
- C08L27/02—Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L27/12—Compositions of homopolymers or 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; Compositions of derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0025—Crosslinking or vulcanising agents; including accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
本出願は、参照により全内容が本明細書に組み込まれている、米国仮特許出願61/046,314号の利益を請求する。
−CF2=CF−O−[CF2]n−CN (式中、nは2〜約12または2〜6の整数);
−CF2=CF−O−[CF2−CF(CF3)−O]n−CF2− (式中、nは0〜4または0〜2の整数);
−CF2=C−[OCF2CF(CF3)]m−O−[CF2]n−CN (式中、mは1〜2の整数、nは1〜4の整数);
−CF2=CF−O−[CF2]n−O−CF(CF3)−CN (式中、nは2〜4の整数);
−CF2=CFOCF2CF(CF((F3)OCF2CF2CN);
−CF2=CF−O[CF2]3−O−CF[CF3]−CN;および
−CF2−CF(O−(CF2)3−O−(CFCF3)−CN)−[CF2−CF(O−CF2−CFCF3−O−CF3−CF2−CN)]
(上記の構造中の「p」は、フルオロポリマーまたはパーフルオロポリマー中に約0.1モル%〜約12モル%、または約1モル%〜約4モル%存在する第2の硬化部位含有モノマーであり、「a」は、約0.1モル%〜約12モル%、または約1モル%〜約7モル%存在する第1の硬化部位含有モノマーを表わす。)などがあげられる。また、共重合体中の第1の硬化部位含有モノマーと第2の硬化部位含有モノマーのモル比は、約1:1〜約10:1または9:1であってもよい。
下記に示すパーフルオロエラストマー組成物A〜Rを、表1に示す成分を混合して調製した。それぞれについて、耐酸素プラズマ性と粘着力のデータを示す。表に示すC1は、比較用の組成物である。
R2 − 350°Fで30分間
R3 − 350°Fで10分間
R4 − 360°Fで10分間
R5 − 360°Fで15分間
R6 − 300°Fで8分間
(ii)官能性ビフェニル系化合物および
式(I):
HON=R1=NOH
(R1は、炭素数1〜10のアルキル基および炭素数1〜10のアリール基から選ばれる)で示されるジオキシム化合物;式(IV):
パーフルオロポリエーテルの少なくとも1種を含む硬化系
を含む硬化性フルオロエラストマー組成物。
で示される化合物から選ばれる、上記1の組成物。
(ii)官能性ビフェニル系化合物および
式(I):
HON=R1=NOH
(R1は、炭素数1〜10のアルキル基および炭素数1〜10のアリール基から選ばれる)で示されるジオキシム化合物;式(IV):
パーフルオロポリエーテル
の少なくとも1種を含む硬化系
を含む硬化性パーフルオロエラストマー組成物。
で示される化合物から選ばれる、上記14の組成物。
式(I):
HON=R1=NOH
(R1は、炭素数1〜10のアルキル基および炭素数1〜10のアリール基から選ばれる)で示されるジオキシム化合物;式(IV):
パーフルオロポリエーテル
の少なくとも1種を含む硬化系を配合し;組成物を硬化時間硬化する、フルオロエラストマー組成物の硬化時間を減少させる方法。
で示される化合物から選ばれる、上記25の方法。
HON=R1=NOH
(R1は、炭素数1〜10のアルキル基および炭素数1〜10のアリール基から選ばれる)で示されるジオキシム化合物およびヘプタフルオロブチリルアミジンからなる硬化系;
平均粒子径が約2〜約25μmの酸化ケイ素;およびポリテトラフルオロエチレン粒子を配合し
(ii)組成物を硬化時間硬化し、耐プラズマ性を発現するパーフルオロエラストマー組成物を得る、耐プラズマ性を発現するパーフルオロエラストマー組成物を製造する方法。
パーフルオロポリエーテルの少なくとも1種
を含む、上記30の方法。
で示される化合物から選ばれる上記30記載の方法。
(ii)官能性ビフェニル系化合物と式(I):
HON=R1=NOH
(R1は、炭素数1〜10のアルキル基および炭素数1〜10のアリール基から選ばれる)で示されるジオキシム化合物;式(IV):
(iii)ポリテトラフルオロエチレン粒子;および
(iv)発煙酸化ケイ素
を含む硬化性パーフルオロエラストマー組成物。
で示される化合物から選ばれる、上記39の組成物。
Claims (12)
- (i)シアノ基を2〜5個有する少なくとも1種の硬化部位含有モノマーを含むフルオロポリマーと
(ii)式(II):
で示される化合物と
式(I):
HON=R1=NOH
(R1は、炭素数1〜10の4価の飽和炭化水素基および炭素数1〜10の4価の芳香族炭化水素基から選ばれる)で示されるジオキシム化合物;
式(IV):
パーフルオロポリエーテル
の少なくとも一種とを含む硬化系を配合し;組成物を硬化時間硬化する、フルオロエラストマー組成物の硬化時間を減少させる方法。 - 硬化系が、ヘプタフルオロブチリルアミジンであるモノアミジン系化合物を含む請求項1記載の方法。
- 硬化系が、アリールジオキシムであるジオキシム化合物を含む請求項1記載の方法。
- フルオロポリマーが、テトラフルオロエチレン、パーフルオロアルキルビニルエーテルおよび少なくとも1種の硬化部位含有モノマーからなる請求項1記載の方法。
- 硬化時間が、(ii)の硬化系を含まない硬化性組成物に比べて約30%〜約60%減少する請求項1記載の方法。
- さらに、キナクリドン、ベンズイミダザロン、インダンスロン、ぺリレン、イソインドリノンおよびイソインドリンから選ばれる着色剤をフルオロポリマーに配合する請求項1記載の方法。
- 着色剤が、キナクリドンである請求項6記載の方法。
- (i)シアノ基を2〜5個有する少なくとも1種の硬化部位含有モノマーを含むパーフルオロエラストマー;
式(II):
で示される官能性ビフェニル系化合物と
式(I):
HON=R1=NOH
(R1は、炭素数1〜10の4価の飽和炭化水素基および炭素数1〜10の4価の芳香族炭化水素基から選ばれる)で示されるジオキシム化合物;
ヘプタフルオロブチリルアミジン;
式(IV):
パーフルオロポリエーテルの少なくとも1種とを含む硬化系;
平均粒子径が約2〜約25μmの酸化ケイ素;
およびポリテトラフルオロエチレン粒子を配合し
(ii)組成物を硬化時間硬化し、耐酸素プラズマ性を発現するパーフルオロエラストマー組成物を得る、耐酸素プラズマ性を発現するパーフルオロエラストマー組成物を製造する方法。 - 硬化系が、ヘプタフルオロブチリルアミジンであるモノアミジン系化合物を含む請求項8記載の方法。
- 硬化系が、アリールジオキシムであるジオキシム化合物を含む請求項8記載の方法。
- パーフルオロエラストマーが、テトラフルオロエチレン、パーフルオロアルキルビニルエーテルおよび少なくとも1種の硬化部位含有モノマーからなる請求項8記載の方法。
- さらに、キナクリドン、ベンズイミダザロン、インダンスロン、ぺリレン、イソインドリノンおよびイソインドリンから選ばれる着色剤をパーフルオロエラストマーに配合する請求項8記載の方法。
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US10604607B2 (en) * | 2015-10-29 | 2020-03-31 | E. I. Du Pont De Nemours And Company | Curable fluoroelastomer composition |
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JP6618506B2 (ja) | 2016-05-30 | 2019-12-11 | 株式会社バルカー | パーフルオロエラストマー組成物及びシール材 |
JP6955384B2 (ja) | 2016-07-13 | 2021-10-27 | 株式会社バルカー | パーフルオロエラストマー組成物及びシール材 |
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