WO2022230706A1 - ビスジアミノフェニル化合物、架橋剤、組成物及び成形品 - Google Patents
ビスジアミノフェニル化合物、架橋剤、組成物及び成形品 Download PDFInfo
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- WO2022230706A1 WO2022230706A1 PCT/JP2022/018031 JP2022018031W WO2022230706A1 WO 2022230706 A1 WO2022230706 A1 WO 2022230706A1 JP 2022018031 W JP2022018031 W JP 2022018031W WO 2022230706 A1 WO2022230706 A1 WO 2022230706A1
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- GRPIQKZLNSCFTB-UHFFFAOYSA-N n-[bis(dimethylamino)-fluoroimino-$l^{5}-phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(=NF)(N(C)C)N(C)C GRPIQKZLNSCFTB-UHFFFAOYSA-N 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- SWMBQMGPRYJSCI-UHFFFAOYSA-N octylphosphane Chemical compound CCCCCCCCP SWMBQMGPRYJSCI-UHFFFAOYSA-N 0.000 description 1
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- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
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- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
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- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
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- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- UJTRRNALUYKHQE-UHFFFAOYSA-N sodium;diphenylmethylbenzene Chemical compound [Na+].C1=CC=CC=C1[C-](C=1C=CC=CC=1)C1=CC=CC=C1 UJTRRNALUYKHQE-UHFFFAOYSA-N 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
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- 238000010186 staining Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- HSVFKFNNMLUVEY-UHFFFAOYSA-N sulfuryl diazide Chemical group [N-]=[N+]=NS(=O)(=O)N=[N+]=[N-] HSVFKFNNMLUVEY-UHFFFAOYSA-N 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
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- XBXCNNQPRYLIDE-UHFFFAOYSA-N tert-butylcarbamic acid Chemical compound CC(C)(C)NC(O)=O XBXCNNQPRYLIDE-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 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
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- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
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- DHWBYAACHDUFAT-UHFFFAOYSA-N tricyclopentylphosphane Chemical compound C1CCCC1P(C1CCCC1)C1CCCC1 DHWBYAACHDUFAT-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 description 1
- SBXWFLISHPUINY-UHFFFAOYSA-N triphenyltin Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)C1=CC=CC=C1 SBXWFLISHPUINY-UHFFFAOYSA-N 0.000 description 1
- IDXDWPWXHTXJMZ-UHFFFAOYSA-N tris(2,4,6-trimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(C)=C1P(C=1C(=CC(C)=CC=1C)C)C1=C(C)C=C(C)C=C1C IDXDWPWXHTXJMZ-UHFFFAOYSA-N 0.000 description 1
- GRPURDFRFHUDSP-UHFFFAOYSA-N tris(prop-2-enyl) benzene-1,2,4-tricarboxylate Chemical compound C=CCOC(=O)C1=CC=C(C(=O)OCC=C)C(C(=O)OCC=C)=C1 GRPURDFRFHUDSP-UHFFFAOYSA-N 0.000 description 1
- XHGIFBQQEGRTPB-UHFFFAOYSA-N tris(prop-2-enyl) phosphate Chemical compound C=CCOP(=O)(OCC=C)OCC=C XHGIFBQQEGRTPB-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
- SANRKQGLYCLAFE-UHFFFAOYSA-H uranium hexafluoride Chemical compound F[U](F)(F)(F)(F)F SANRKQGLYCLAFE-UHFFFAOYSA-H 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
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- 239000002699 waste material Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 1
- UGOMMVLRQDMAQQ-UHFFFAOYSA-N xphos Chemical group CC(C)C1=CC(C(C)C)=CC(C(C)C)=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 UGOMMVLRQDMAQQ-UHFFFAOYSA-N 0.000 description 1
- ZVWKZXLXHLZXLS-UHFFFAOYSA-N zirconium nitride Chemical compound [Zr]#N ZVWKZXLXHLZXLS-UHFFFAOYSA-N 0.000 description 1
Classifications
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- 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
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/55—Diphenylamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
- C07C211/56—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/44—Nitrogen atoms attached in position 4 with aryl radicals attached to said nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D241/20—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/50—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to ring nitrogen atoms
- C07D241/54—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
-
- 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
- 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
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F214/00—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
- C08F214/18—Monomers containing fluorine
- C08F214/26—Tetrafluoroethene
- C08F214/262—Tetrafluoroethene with fluorinated vinyl ethers
Definitions
- the present disclosure relates to bisdiaminophenyl compounds, crosslinkers, compositions and shaped articles.
- Patent Document 1 as a cross-linking agent for a fluorine-containing elastomer, (A) formula (I): A compound containing at least two crosslinkable reactive groups (I) represented by (wherein R 1 is the same or different and both are fluorine atoms or monovalent organic groups) has been proposed.
- An object of the present disclosure is to provide a novel compound that can be used as a cross-linking agent that provides a cross-linked product with excellent plasma resistance while maintaining heat resistance, a cross-linking agent using the compound, a composition, and a molded article.
- R 1 is —SO 2 —, —O—, —CO—, an optionally substituted alkylene group, the formula is a group or a single bond, and two A are independently an aromatic ring group containing a 5- or 6-membered aromatic ring (provided that a 6-membered aromatic If it is a monocyclic aromatic ring group containing a hydrocarbon ring, it has a substituent.).
- R 1 is —SO 2 —, —O—, —CO—, an optionally substituted alkylene group, the formula is a group or a single bond, and two A are independently an aromatic ring group containing a 5- or 6-membered aromatic ring (provided that a 6-membered aromatic If it is a monocyclic aromatic ring group containing a hydrocarbon ring, it has a substituent.).
- the aromatic ring group is a monocyclic aromatic ring group containing a 6-membered aromatic hydrocarbon ring having a substituent, or a monocyclic ring containing a 5- or 6-membered aromatic heterocyclic ring containing a nitrogen atom or a sulfur atom. It is preferably an aromatic ring group.
- the aromatic ring group is preferably a group exhibiting a ⁇ -electron deficient property rather than a benzene ring.
- the substituent is preferably at least one selected from the group consisting of halogen atoms and alkyl groups optionally having halogen atoms.
- the present disclosure also relates to cross-linking agents comprising the above compounds.
- the present disclosure also relates to a composition comprising a fluorine-containing elastomer and the compound or the cross-linking agent.
- the fluorine-containing elastomer has a crosslinkable group, and the crosslinkable group is a hydroxyl group (--OH), a cyano group (--CN), a carboxyl group (--COOH), an alkoxycarbonyl group, or an acid halide group. It is preferably at least one selected from the group consisting of:
- the present disclosure also relates to shaped articles obtained by cross-linking the above compositions.
- the compound of the present disclosure can be used as a cross-linking agent that provides a cross-linked product with excellent plasma resistance while maintaining heat resistance.
- the cross-linking agent and composition of the present disclosure can provide a cross-linked product with excellent plasma resistance while maintaining heat resistance.
- the molded article of the present disclosure has excellent plasma resistance while maintaining heat resistance.
- the present disclosure provides the following general formula (1): It relates to a compound represented by
- R 1 is —SO 2 —, —O—, —CO—, an optionally substituted alkylene group, the formula is a group or a single bond represented by
- Preferred specific examples of the optionally substituted alkylene group include, but are not limited to, an unsubstituted alkylene group having 1 to 6 carbon atoms, a perfluoroalkylene group having 1 to 10 carbon atoms, and the like.
- the perfluoroalkylene group A group represented by is preferred.
- R 1 may be bonded to any position on the left or right benzene ring, but since synthesis is easy and the cross-linking reaction proceeds easily, either NH 2 group or amino group substituted with aromatic ring group A It is preferable that the two are bonded so as to be at the para position.
- two A are independently an aromatic ring group containing a 5- or 6-membered aromatic ring optionally having a substituent (provided that the 6-membered aromatic hydrocarbon ring is If it is a monocyclic aromatic ring group, it has a substituent.). Since A is the above aromatic ring group, when the above compound is used as a cross-linking agent, plasma resistance (especially oxygen plasma resistance) can be improved while maintaining the heat resistance of the cross-linked product. It is also possible to obtain a crosslinked product having good compression set properties and crack resistance. Further, when A is the above aromatic ring group, the melting point of the above compound can be increased, and contamination of the mold during molding can be reduced, which is industrially advantageous.
- the aromatic ring is preferably an aromatic hydrocarbon ring or an aromatic heterocyclic ring.
- the aromatic ring group contains an aromatic hydrocarbon ring, it is preferably monocyclic or polycyclic, more preferably monocyclic.
- the above-mentioned aromatic ring group containing an aromatic hydrocarbon ring does not include an aromatic ring group containing an aromatic heterocycle described later.
- aromatic ring group containing an aromatic hydrocarbon ring examples include a phenyl group, naphthyl (eg, 1-naphthyl, 2-naphthyl) group, biphenyl (eg, 2-biphenyl, 3-biphenyl, 4-biphenyl). groups, anthryl (eg, 2-anthryl) groups, and the like.
- the aromatic ring group containing the aromatic hydrocarbon ring may have one or more substituents.
- a monocyclic aromatic ring group (phenyl group) containing a 6-membered aromatic hydrocarbon ring must have a substituent.
- the number of substituents is preferably 1 to 5, more preferably 1 to 3, even more preferably 1 to 2.
- the substituent include halogen atoms (fluorine atom, chlorine atom, etc.), alkyl groups optionally having a halogen atom, and the like.
- a fluorine atom is preferable as the halogen atom.
- the alkyl group preferably has 1 to 5 carbon atoms, more preferably 1 to 2 carbon atoms, and even more preferably 1 carbon atom.
- At least one selected from the group consisting of a halogen atom and an alkyl group optionally having a halogen atom is preferable, and a fluorine atom and an alkyl group optionally having a fluorine atom More preferably at least one selected from the group consisting of, more preferably at least one selected from the group consisting of a fluorine atom and a fluoroalkyl group, from the group consisting of a fluorine atom and a fluoroalkyl group having 1 to 5 carbon atoms At least one selected is even more preferred, and at least one selected from the group consisting of a fluorine atom and a trifluoromethyl group is particularly preferred.
- the heat resistance, plasma resistance, compression set property and crack resistance of the crosslinked product can be improved.
- the melting point of the compound can be increased, and contamination of the mold during molding can be reduced, which is industrially advantageous.
- the aromatic ring group containing the aromatic hydrocarbon ring is a 6-membered aromatic hydrocarbon having a substituent.
- a 6-membered aromatic hydrocarbon ring which is preferably a monocyclic aromatic ring group containing a hydrogen ring and has at least one selected from the group consisting of a halogen atom and an alkyl group optionally having a halogen atom is more preferably a monocyclic aromatic ring group containing a 6-membered aromatic hydrocarbon ring having at least one selected from the group consisting of a fluorine atom and an alkyl group optionally having a fluorine atom -C 6 H 5-n Rf n (wherein Rf is a fluorine atom or a fluoroalkyl group, n is an integer of 1 to 5) or -C 6 H 5 -m R m (wherein R is an alkyl group and m is an integer
- the aromatic ring group containing an aromatic hydrocarbon ring is also preferably —C 6 H 5-m R m (wherein R is an alkyl group and m is an integer of 1 to 5).
- the substituent may be located at any of the ortho-, meta-, and para-positions relative to the nitrogen atom to which A binds in general formula (1). For ease of synthesis, it may be located at the ortho- or meta-position relative to the nitrogen atom to which A bonds in general formula (1).
- the number of carbon atoms in the fluoroalkyl group as Rf is preferably 1 to 5, more preferably 1 to 2, and even more preferably 1.
- the fluoroalkyl group as Rf is preferably a trifluoromethyl group.
- Rf is preferably located at the ortho- or meta-position relative to the nitrogen atom to which A binds in general formula (1).
- n is preferably an integer of 1 to 3, more preferably 1 or 2, even more preferably 2.
- the above alkyl group for R preferably does not have a substituent such as a fluorine atom.
- the number of carbon atoms in the alkyl group is preferably 1 to 5, more preferably 1 to 2, even more preferably 1.
- R is preferably located at the ortho-position or meta-position, more preferably at the ortho-position, with respect to the nitrogen atom to which A binds in general formula (1).
- m is preferably an integer of 1 to 3, more preferably 1 or 2, and more preferably 1.
- the heteroaromatic ring contains one or more heteroatoms.
- the heteroatom is preferably at least one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, preferably at least one selected from the group consisting of a nitrogen atom and a sulfur atom, and more preferably a nitrogen atom. .
- the aromatic ring group containing the aromatic heterocycle is preferably monocyclic or condensed ring, more preferably monocyclic.
- the aromatic ring group When the aromatic ring group is of a condensed ring type, it may have a structure in which aromatic heterocycles are condensed with each other, or a structure in which an aromatic heterocycle and an aromatic hydrocarbon ring are condensed.
- the aromatic ring group When the aromatic ring group is condensed, it may be bicyclic, tricyclic, or the like, but is preferably bicyclic.
- the aromatic ring group containing the aromatic heterocycle may or may not have a substituent.
- substituents include an alkyl group, a fluoroalkyl group, a fluorine atom, a chlorine atom, etc., and at least one selected from the group consisting of a fluorine atom and a fluoroalkyl group is preferable, and a fluorine atom and a C 1-5 group are preferred. is more preferably at least one selected from the group consisting of a fluoroalkyl group, and more preferably at least one selected from the group consisting of a fluorine atom and a trifluoromethyl group.
- the aromatic ring group containing an aromatic heterocycle is preferably an aromatic ring group containing a 5- or 6-membered aromatic heterocycle containing a nitrogen atom or a sulfur atom, and a 6-membered aromatic heterocycle containing a nitrogen atom. More preferably an aromatic ring group containing a nitrogen atom, more preferably a monocyclic or bicyclic aromatic ring group containing a 6-membered aromatic heterocycle containing a nitrogen atom, a monocyclic ring containing a 6-membered aromatic heterocycle containing a nitrogen atom
- aromatic ring groups are particularly preferred.
- the aromatic ring group containing the above aromatic heterocycle is also preferably pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, quinolyl group, quinoxalinyl group, more preferably pyridyl group, pyrazinyl group, pyrimidinyl group, triazinyl group, A pyridyl group is more preferred.
- the aromatic ring group is preferably a group exhibiting a ⁇ -electron deficiency (lower ⁇ -electron density) than a benzene ring (a phenyl group having no substituents).
- the crosslinked structure exhibits ⁇ -electron deficiency when the compound is used as a crosslinking agent, so that a crosslinked product having excellent oxidation resistance can be obtained. It is also possible to provide a crosslinked product with even better heat resistance, plasma resistance, compression set characteristics and crack resistance.
- —C 6 H 5-n Rf n (wherein Rf is a fluorine atom or a fluoroalkyl group, and n is an integer of 1 to 5), or an aromatic ring group containing a 6-membered aromatic heterocyclic ring containing a nitrogen atom preferably —C 6 H 5-n Rf n (wherein Rf is a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms, and n is an integer of 1 to 5), or a 6-membered aromatic heterocyclic ring containing a nitrogen atom More preferably, a monocyclic or bicyclic aromatic ring group containing —C 6 H 5-n Rf n (wherein Rf is a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms, and n is an integer of 1 to 5), or a 6-
- the aromatic ring group may be a group exhibiting ⁇ -electron excess (having a high ⁇ -electron density) relative to a benzene ring (phenyl group having no substituents).
- the compound of the present disclosure can improve the cross-linking rate (T90) and promote cross-linking when the compound is used as a cross-linking agent.
- Crosslinking can also be promoted when used in combination with a crosslinker having a group exhibiting a ⁇ electron deficiency relative to the benzene ring.
- —C 6 H 5-m R m (wherein R is an alkyl group and m is an integer of 1 to 5) is preferred, —C 6 H 5-m R m (wherein R is an alkyl group having 1 to 5 carbon atoms and m is an integer of 1 to 5) is more preferable, —C 6 H 5-m R m (wherein R is a methyl group (—CH 3 ) and m is an integer of 1 to 5) is more preferred.
- the said alkyl group does not have a substituent.
- the above compound has the following general formula (1-1):
- A is as described above.
- the compound of the general formula (1-1) (wherein the two A's are independently —C 6 H 5-m R m (in the formula, R is an alkyl group, and m is an integer of 1 to 5).
- General formula (1-1) above (wherein two A are independently —C 6 H 5-m R m (wherein R is an alkyl group having 1 to 5 carbon atoms, m is an integer of 1 to 5 ) is more preferably a compound represented by General formula (1-1) above (wherein the two A are independently —C 6 H 5-m R m (wherein R is a methyl group (—CH 3 ) and m is an integer of 1 to 5) is more preferred.
- Rf represents a fluorine atom or a fluoroalkyl group, preferably a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms, more preferably a fluorine atom or a trifluoromethyl group.
- Rf represents a fluorine atom or a fluoroalkyl group, preferably a fluorine atom or a fluoroalkyl group having 1 to 5 carbon atoms, more preferably a fluorine atom or a trifluoromethyl group
- R represents an alkyl group, preferably an alkyl group having 1 to 5 carbon atoms, more preferably a methyl group (--CH 3 ).
- a compound represented by is preferred.
- a compound represented by is preferred.
- the compound preferably has a melting point of 100° C. or higher, more preferably 120° C. or higher, and even more preferably 130° C. or higher.
- the melting point is preferably 300° C. or lower, more preferably 280° C. or lower, and even more preferably 260° C. or lower.
- the melting point is the temperature corresponding to the maximum value in the heat of fusion curve when the temperature is raised at a rate of 10° C./min using a thermogravimetric differential thermal analyzer [TG-DTA].
- step (2) to obtain a compound (102) represented by Compound (102) and general formula (103): (In general formula (103), A is as described above.) by reacting with compound (103) represented by general formula (104): (In the general formula (104), R 1 and A are as described above.)
- a step (3) of obtaining a compound (104), and It can be preferably produced by a production method including the step (4) of reducing the compound (104) to obtain the compound represented by the general formula (1).
- the substituent which the hydrocarbon group as R 2 in Y of the general formula (102) may have is preferably a halogen atom, a nitro group or an alkyl group, more preferably a fluorine atom or a nitro group.
- R 2 is preferably an optionally substituted alkyl group or an optionally substituted phenyl group, more preferably a methyl group, a trifluoromethyl group, a tolyl group, or a nitrophenyl group.
- Nitration in step (1) can be carried out by reacting compound (100) with a nitrating agent such as nitric acid, and conventionally known reaction conditions can be employed.
- a nitrating agent such as nitric acid
- Sulfonylation in step (2) can be carried out by reacting compound (101) with a sulfonylating agent.
- tosylate chloride, trifluoromethanesulfonic anhydride, trifluoromethanesulfonic acid chloride, and trifluoromethanesulfonic acid bromide are preferable, and trifluoro Rmethanesulfonic anhydride, trifluoromethanesulfonic acid chloride and trifluoromethanesulfonic acid bromide are more preferable, and trifluoromethanesulfonic anhydride and trifluoromethanesulfonic acid chloride are particularly preferable.
- the sulfonylating agent is preferably used in an amount of 0.8 to 10 mol, more preferably 1.0 to 5 mol, per 1 mol of compound (101).
- the above sulfonylation is preferably carried out in the presence of a base.
- the base include amines and inorganic bases.
- the above amine include triethylamine, tri(n-propyl)amine, tri(n-butyl)amine, diisopropylethylamine, cyclohexyldimethylamine, pyridine, lutidine, ⁇ -collidine, N,N-dimethylaniline, N-methyl piperidine, N-methylpyrrolidine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]-5-nonene, 1 , 4-diazabicyclo[2.2.2]octane (DABCO), 4-dimethylaminopyridine (DMAP), proton sponge and the like.
- DBU 1,8-diazabicyclo[5.4.0]-7-undecene
- Examples of the inorganic base include lithium hydroxide, potassium hydroxide, sodium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium carbonate, cesium hydrogen carbonate, and hydrogen carbonate.
- Examples include lithium, cesium fluoride, potassium fluoride, sodium fluoride, lithium chloride, and lithium bromide.
- amines are preferable, and triethylamine, tributylamine, 4-dimethylaminopyridine (DMAP), and pyridine are more preferable.
- the base is preferably used in an amount of 0.001 to 7 mol, more preferably 0.1 to 3 mol, per 1 mol of compound (101).
- the sulfonylation can be carried out in a solvent.
- organic solvents are preferable, and non-aromatic hydrocarbon solvents such as pentane, hexane, heptane, octane, cyclohexane, decahydronaphthalene, n-decane, isododecane, and tridecane; benzene, toluene, xylene, tetralin, veratrol, Aromatic hydrocarbon solvents such as diethylbenzene, methylnaphthalene, nitrobenzene, o-nitrotoluene, mesitylene, indene, and diphenyl sulfide; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, propiophenone, diisobutyl ketone, and isophorone; Dichloromethane, chloro
- the sulfonylation temperature is preferably -20 to 80°C, more preferably 0 to 50°C.
- the sulfonylation pressure is preferably 0.05 to 0.20 MPa, more preferably 0.07 to 0.15 MPa.
- the sulfonylation time is preferably 0.5 to 24 hours, more preferably 1 to 15 hours.
- step (3) it is preferable to use 1.0 to 20 mol, more preferably 1.0 to 5.0 mol, of compound (103) per 1 mol of compound (102).
- the reaction of step (3) is preferably carried out in the presence of a palladium catalyst.
- the palladium catalyst is not particularly limited, but is preferably an organic palladium complex.
- the palladium catalyst examples include a zero-valent palladium complex; a zero-valent palladium complex generated during the reaction from a II-valent palladium complex; and at least one compound selected from the group consisting of diketones, phosphines, diamines and bipyridyls ( ligand) and the like obtained by mixing.
- the above zerovalent palladium complex is not particularly limited, but examples include Pd 2 (DBA) 3 (DBA is dibenzylideneacetone), Pd(COD) 2 (COD is cycloocta-1,5-diene), Pd(DPPE ) (DPPE is 1,2-bisdiphenylphosphinoethane), Pd(PCy 3 ) 2 (Cy is a cyclohexyl group), Pd(Pt—Bu 3 ) 2 (t-Bu is a t-butyl group) and Pd(PPh 3 ) 4 (Ph is a phenyl group) and the like.
- DBA dibenzylideneacetone
- Pd(COD) 2 COD is cycloocta-1,5-diene
- Pd(DPPE ) DPPE is 1,2-bisdiphenylphosphinoethane
- Pd(PCy 3 ) 2 Cy is a cyclohexyl group
- divalent palladium complex examples include palladium chloride, palladium bromide, palladium acetate, bis(acetylacetonato)palladium(II), dichloro( ⁇ 4-1,5-cyclooctadiene)palladium(II), or these and a complex in which a phosphine ligand such as triphenylphosphine is coordinated.
- the phosphine ligand-coordinated complex includes dichloro[1,2-bis(diphenylphosphino)ethane]palladium (II), dichloro[1,3-bis(diphenylphosphino)propane]palladium(II), dichloro[1,4-bis(diphenylphosphino)butane]palladium(II), dichloro[1,5-bis(diphenylphosphino)pentane]palladium(II), dichloro[bis(diphenylphosphinophenyl)ether]palladium(II), dichloro[bis(dicyclohexylphosphinophenyl)ether]palladium(II), dichloro[4,5-bis(diphenylphosphino)-9,9′-dimethylxanthene]palladium(II), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(I
- the above-described zerovalent palladium complex or the zerovalent palladium complex produced by reduction from the IIvalent palladium complex acts with a compound (ligand) such as a diketone, phosphine, diamine, bipyridyl, etc., which is added as necessary during the reaction. can also be converted into a zerovalent palladium complex that participates in the reaction. It should be noted that it is not necessarily clear how many of these ligands are coordinated to the zerovalent palladium complex during the reaction.
- ligand such as a diketone, phosphine, diamine, bipyridyl, etc.
- These palladium complexes are often used in the reaction by forming a uniform solution with the reaction substrate by using the above ligands. Alternatively, it can be used as a supported heterogeneous catalyst.
- Such heterogeneous catalysts have process advantages such as catalyst recovery.
- a specific catalyst structure for example, a polymer phosphine in which phosphine is introduced into a crosslinked polystyrene (PS) chain, as shown in the chemical formula below, is used to fix metal atoms.
- PS polystyrene
- JP-A-06-32763 JP-A-2005-281454
- Polymer phosphines described in JP-A-2009-527352 can also be used.
- PS indicates polystyrene and Ph indicates a phenyl group.
- diketone examples include ⁇ -diketone such as acetylacetone, 1-phenyl-1,3-butanedione and 1,3-diphenylpropanedione.
- the phosphine examples include one or more substituents selected from the group consisting of an optionally substituted alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, and the like. It can be a phosphine having on the phosphorus atom. Among them, tri(cyclo)alkylphosphine, triarylphosphine, and Buchwald ligand are preferred.
- tri(cyclo)alkylphosphine examples include tricyclohexylphosphine, triisopropylphosphine, tri-t-butylphosphine, trithexylphosphine, triadamantylphosphine, tricyclopentylphosphine, di-t-butylmethylphosphine, tribicyclo [2,2,2]octylphosphine, tri(C3-20(cyclo)alkyl)phosphine such as trinorbornylphosphine, and the like.
- triarylphosphines include tri(monocyclic aryl)phosphines such as triphenylphosphine, trimesitylphosphine and tri(o-tolyl)phosphine.
- Buchwald ligands include 2-dicyclohexylphosphino-2'-(N,N-dimethylamino)biphenyl, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, 2-dicyclohexylphosphino -2',6'-dimethoxybiphenyl, 2-di-tert-butylphosphino-2',4',6'-triisopropylbiphenyl, (2-biphenyl)dicyclohexylphosphine, (2-biphenyl)di-tert- Butylphosphine, 2-dicyclohexylphosphino-2',
- triphenylphosphine tricyclohexylphosphine and tri-t-butylphosphine are preferred.
- arylphosphines for heterogeneous catalysts in which phosphine units are introduced into polymer chains can also be preferably used.
- triarylphosphine in which one phenyl group of triphenylphosphine is bound to a polymer chain, as shown in the chemical formula below, is exemplified.
- PS indicates polystyrene and Ph indicates a phenyl group.
- diamine examples include tetramethylethylenediamine and 1,2-diphenylethylenediamine.
- phosphines diamines and bipyridyls are preferred, triarylphosphines are more preferred, and triphenylphosphine is particularly preferred.
- the palladium catalyst is preferably used in an amount of 0.002 to 40 mol, more preferably 0.02 to 30 mol, and 0.1 to 20 mol, per 1 mol of compound (102). More preferably, it is particularly preferable to use 1 to 20 mol.
- the reaction of step (3) is preferably carried out in the presence of a base.
- the bases include amines, inorganic bases, and organometallic bases.
- the amine include triethylamine, tri(n-propyl)amine, tri(n-butyl)amine, diisopropylethylamine, cyclohexyldimethylamine, pyridine, lutidine, ⁇ -collidine, N,N-dimethylaniline, N-methyl piperidine, N-methylpyrrolidine, N-methylmorpholine, 1,8-diazabicyclo[5.4.0]-7-undecene (DBU), 1,5-diazabicyclo[4.3.0]-5-nonene, 1 , 4-diazabicyclo[2.2.2]octane (DABCO), 4-dimethylaminopyridine (DMAP), proton sponge and the like.
- DBU 1,8-diazabicyclo[5.4.0]-7-undecene
- Examples of the inorganic base include lithium hydroxide, potassium hydroxide, sodium hydroxide, calcium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, cesium carbonate, cesium hydrogen carbonate, and hydrogen carbonate. Lithium, cesium fluoride, potassium fluoride, sodium fluoride, lithium chloride, lithium bromide and the like.
- organic metal base examples include organic alkali metal compounds such as butyllithium, t-butyllithium, phenyllithium, triphenylmethylsodium and ethylsodium; methylmagnesium bromide, dimethylmagnesium, phenylmagnesium chloride, phenylcalcium bromide, organic alkaline earth metal compounds such as (dicyclopentadiene)calcium; alkoxides such as sodium methoxide and t-butyl methoxide;
- the base include, among others, cesium carbonate, cesium hydrogen carbonate, cesium fluoride, triethylamine, tri(n-propyl)amine, tri(n-butyl)amine, pyridine, lutidine, ⁇ -collidine, 1,8-diazabicyclo [5.4.0]-7-undecene (DBU) is preferred.
- DBU 1,8-diazabicyclo [5.4.0]-7-undecene
- the base is preferably used in an amount of 0.5 to 10 mol, more preferably 1 to 6 mol, per 1 mol of compound (102).
- the reaction of step (3) can be carried out in a solvent.
- organic solvents are preferable, and non-aromatic hydrocarbon solvents such as pentane, hexane, heptane, octane, cyclohexane, decahydronaphthalene, n-decane, isododecane, and tridecane; benzene, toluene, xylene, tetralin, veratrol, Aromatic hydrocarbon solvents such as diethylbenzene, methylnaphthalene, nitrobenzene, o-nitrotoluene, mesitylene, indene, diphenyl sulfide; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, acetophenone, propiophenone, diisobutyl ketone, isophorone; dichloromethane, chloroform , chloro
- the reaction temperature of step (3) is preferably 20 to 150°C, more preferably 50 to 130°C.
- the reaction pressure in step (3) is preferably 0.05 to 0.20 MPa, more preferably 0.07 to 0.15 MPa.
- the reaction time in step (3) is preferably 0.5 to 48 hours, more preferably 1 to 24 hours.
- Reduction in step (4) can be carried out by contacting compound (104) with a reducing agent such as hydrogen in the presence of a palladium catalyst such as palladium carbon, and conventionally known reaction conditions can be employed.
- a reducing agent such as hydrogen
- a palladium catalyst such as palladium carbon
- the product may be separated and purified by distilling off the solvent, column chromatography, recrystallization, or the like.
- the compound of the present disclosure can be suitably used as a cross-linking agent that provides a cross-linked product excellent in plasma resistance (especially oxygen plasma resistance) while maintaining heat resistance. It can also be suitably used as a cross-linking agent that gives a cross-linked product having good compression set properties and crack resistance.
- a cross-linking agent that provides a cross-linked product excellent in plasma resistance (especially oxygen plasma resistance) while maintaining heat resistance.
- It can also be suitably used as a cross-linking agent that gives a cross-linked product having good compression set properties and crack resistance.
- the compounds of the present disclosure can also be suitably used as monomers for super engineering plastics.
- a crosslinker comprising a compound of the present disclosure is also an aspect of the present disclosure.
- the cross-linking agent is preferably a fluorine-containing elastomer cross-linking agent. Further, the cross-linking agent is preferably an imidazole cross-linking agent.
- the present disclosure also relates to compositions comprising a fluorine-containing elastomer and a compound of the present disclosure or a crosslinker of the present disclosure as described above.
- a cross-linked product having excellent plasma resistance (particularly oxygen plasma resistance) while maintaining heat resistance can be obtained.
- a crosslinked product having good compression set properties and crack resistance is also obtained.
- the fluorine-containing elastomer may be a partially fluorinated elastomer or a perfluoroelastomer, but it is preferable to use a perfluoroelastomer because it is more excellent in chemical resistance and heat resistance.
- Partially fluorinated elastomers include vinylidene fluoride (VdF)-based fluororubbers, tetrafluoroethylene (TFE)/propylene (Pr)-based fluororubbers, and tetrafluoroethylene (TFE)/propylene/vinylidene fluoride (VdF)-based fluororubbers.
- VdF vinylidene fluoride
- TFE tetrafluoroethylene
- Pr propylene
- VdF tetrafluoroethylene
- VdF tetrafluoroethylene
- HFP ethylene/hexafluoropropylene
- HFP ethylene/hexafluoropropylene
- VdF vinylidene fluoride
- HFP ethylene/hexafluoropropylene
- TFE tetrafluoroethylene
- the vinylidene fluoride-based fluororubber consists of 45 to 85 mol% of polymerized units based on vinylidene fluoride and 55 to 15 mol% of polymerized units based on at least one other monomer copolymerizable with vinylidene fluoride.
- a copolymer is preferred.
- Preferred is a copolymer comprising 50 to 80 mol % of polymerized units based on vinylidene fluoride and 50 to 20 mol % of polymerized units based on at least one other monomer copolymerizable with vinylidene fluoride.
- each monomer constituting the fluorine-containing elastomer can be calculated by appropriately combining NMR, FT-IR, elemental analysis, and fluorescent X-ray analysis depending on the type of monomer.
- CF 2 CF-ORf 81 (Wherein, Rf 81 represents a perfluoroalkyl group having 1 to 8 carbon atoms.)
- CF 2 CFOCF 2 ORf 101 (In the formula, Rf 101 is a linear or branched perfluoroalkyl group having 1 to 6 carbon atoms, a cyclic perfluoroalkyl group having 5 to 6 carbon atoms, or a is a linear or branched perfluorooxyalkyl group), and
- CF2 CFO( CF2CF (Y11)O) m ( CF2) nF (wherein Y 11 represents a fluorine atom or a trifluoro
- vinylidene fluoride-based fluorororubbers include VdF/HFP rubber, VdF/HFP/TFE rubber, VdF/CTFE rubber, VdF/CTFE/TFE rubber, and VdF/ represented by general formula (6).
- fluoromonomer-based rubber VdF/fluoromonomer represented by general formula (6)/TFE-based rubber
- VdF/perfluoro(methyl vinyl ether) [PMVE]-based rubber VdF/PMVE/TFE-based rubber, VdF/PMVE/ TFE/HFP-based rubber and the like can be mentioned.
- the tetrafluoroethylene/propylene fluororubber contains 45 to 70 mol% of polymerized units based on tetrafluoroethylene, 55 to 30 mol% of polymerized units based on propylene, and 0 to 5 polymerized units based on a fluoromonomer that provides a crosslinking site. It is preferably a copolymer consisting of mol %.
- the fluorine-containing elastomer may be a perfluoroelastomer.
- the perfluoroelastomer include perfluoroelastomers containing polymerized units based on TFE, such as TFE/fluoromonomer copolymers represented by general formula (8), (10) or (11) and TFE/general formula (8 ), (10) or (11), or at least one selected from the group consisting of the fluoromonomers/monomer copolymers that provide cross-linking sites.
- TFE/PMVE copolymer the composition is preferably 45-90/10-55 (mol %), more preferably 55-80/20-45, still more preferably 55- It is 70/30-45.
- the ratio is preferably 45-89.9/10-54.9/0.01-4 (mol %), more preferably 55-77. 9/20-49.9/0.1-3.5, more preferably 55-69.8/30-44.8/0.2-3.
- TFE/a fluoromonomer copolymer represented by general formula (8), (10) or (11) having 4 to 12 carbon atoms it is preferably 50 to 90/10 to 50 (mol%). , more preferably 60-88/12-40, still more preferably 65-85/15-35.
- perfluoroelastomer examples include TFE/fluoromonomer represented by general formula (11)/fluoromonomer copolymer that provides a crosslinking site, TFE/perfluorovinyl ether copolymer represented by general formula (11), and TFE.
- TFE/fluoromonomer represented by general formula (11) perfluoromonomer copolymer that provides a crosslinking site
- TFE/perfluorovinyl ether copolymer represented by general formula (11) examples of the perfluoroelastomer.
- At least one selected from the group consisting of /fluoromonomer copolymer represented by general formula (8), and TFE/fluoromonomer represented by general formula (8)/monomer copolymer that provides a crosslinking site is preferably
- perfluoroelastomer examples include those described in International Publication No. 97/24381, Japanese Patent Publication No. 61-57324, Japanese Patent Publication No. 4-81608, Japanese Patent Publication No. 5-13961, etc. can be done.
- a monomer that provides a cross-linking site is a monomer (cure site monomer) having a cross-linking group that provides the fluoropolymer with a cross-linking site for forming a cross-linking with a cross-linking agent.
- CX 3 2 CX 3 —R f 121 CHR 121 X 4 (Wherein, X 3 is a hydrogen atom, a fluorine atom or CH 3 , R f 121 is a fluoroalkylene group, a perfluoroalkylene group, a fluoro(poly)oxyalkylene group or a perfluoro(poly)oxyalkylene group, R 121 is a hydrogen atom or CH 3 , X 4 is an iodine atom or a bromine atom),
- CX 3 2 CX 3 -R f 131 X 4 (Wherein, X 3 is a hydrogen atom, a fluorine atom or CH 3 , R f 131 is a fluoroalkylene group, a perfluoroalkylene group, a fluoropolyoxyalkylene group or a perfluoro
- X3 is preferably a fluorine atom.
- R f 121 and R f 131 are preferably perfluoroalkylene groups having 1 to 5 carbon atoms.
- R 121 is preferably a hydrogen atom.
- X5 is preferably a cyano group, an alkoxycarbonyl group, an iodine atom, a bromine atom, or -CH2I .
- X 6 is preferably a cyano group, an alkoxycarbonyl group, an iodine atom, a bromine atom, or -CH 2 OH.
- CF2 CFOCF2CF2CH2I
- CH2 CFCF2OCF ( CF3 ) CF2OCF ( CF3 )CN
- CH2 CFCF2OCF ( CF3 ) CF2 OCF( CF3 )COOH
- CH2 CFCF2OCF( CF3 ) CF2OCF ( CF3 ) CH2OH
- CH2 CHCF2CF2I
- the fluorine-containing elastomer preferably has a glass transition temperature of ⁇ 70° C. or higher, more preferably ⁇ 60° C. or higher, and preferably ⁇ 50° C. or higher, in terms of excellent compression set properties at high temperatures. More preferred. From the viewpoint of good cold resistance, the temperature is preferably 5°C or lower, more preferably 0°C or lower, and even more preferably -3°C or lower.
- the glass transition temperature is obtained by obtaining a DSC curve by heating 10 mg of a sample at 20 ° C./min using a differential scanning calorimeter (manufactured by Mettler Toledo, DSC822e), and obtaining a DSC curve before and after the secondary transition of the DSC curve. It can be obtained as the temperature at the midpoint of the two intersections of the extension of the line and the tangent line at the point of inflection of the DSC curve.
- the fluorine-containing elastomer preferably has a Mooney viscosity ML(1+20) at 170° C. of 30 or more, more preferably 40 or more, even more preferably 50 or more, in terms of good heat resistance. From the viewpoint of good workability, it is preferably 150 or less, more preferably 120 or less, and even more preferably 110 or less.
- the fluorine-containing elastomer preferably has a Mooney viscosity ML(1+20) at 140° C. of 30 or more, more preferably 40 or more, even more preferably 50 or more, in terms of good heat resistance. From the viewpoint of good workability, it is preferably 180 or less, more preferably 150 or less, and even more preferably 110 or less.
- the fluorine-containing elastomer preferably has a Mooney viscosity ML(1+10) at 100° C. of 10 or more, more preferably 20 or more, and even more preferably 30 or more, in terms of good heat resistance. From the viewpoint of good workability, it is preferably 120 or less, more preferably 100 or less, and even more preferably 80 or less.
- the Mooney viscosity can be measured according to JIS K6300 at 170°C, 140°C, and 100°C using a Mooney viscometer MV2000E manufactured by ALPHA TECHNOLOGIES.
- the partially fluorinated elastomers and perfluoroelastomers described above can be produced by conventional methods.
- An iodine compound or a bromine compound can also be used as a chain transfer agent because it is possible to
- the polymerization method using an iodine compound or a bromine compound includes, for example, a method of conducting emulsion polymerization in an aqueous medium under pressure in the presence of an iodine compound or a bromine compound in a substantially oxygen-free state. (iodine transfer polymerization method).
- iodine compound or bromine compound to be used include, for example, the general formula: R 13 I x Br y (Wherein, x and y are each an integer of 0 to 2 and satisfy 1 ⁇ x + y ⁇ 2, and R 13 is a saturated or unsaturated fluorohydrocarbon group having 1 to 16 carbon atoms or chlorofluoro a hydrocarbon group, or a hydrocarbon group having 1 to 3 carbon atoms, which may contain an oxygen atom).
- an iodine compound or a bromine compound an iodine atom or a bromine atom is introduced into the polymer and functions as a cross-linking point.
- iodine compounds and bromine compounds include 1,3-diiodoperfluoropropane, 2-iodoperfluoropropane, 1,3-diiodoperfluoropropane, 1,4-diiodoperfluorobutane, 1 ,5-diiodo-2,4-dichloroperfluoropentane, 1,6-diiodoperfluorohexane, 1,8-diiodoperfluorooctane, 1,12-diiodoperfluorododecane, 1,16-diiodine perfluorohexadecane, diiodomethane, 1,2-diiodoethane, 1,3-diiodo-n - propane, CF2Br2 , BrCF2CF2Br , CF3CFBrCF2Br , CFClBr2 , BrCF2C
- 1,4-diiodoperfluorobutane, 1,6-diiodoperfluorohexane, and 2-iodoperfluoropropane are used from the viewpoint of polymerization reactivity, cross-linking reactivity, availability, etc. is preferred.
- the fluorine-containing elastomer preferably has a crosslinkable group capable of reacting with the crosslinkable reactive group of the compound of the present disclosure.
- the crosslinkable group is preferably at least one selected from the group consisting of a hydroxy group (--OH), a cyano group (--CN), a carboxyl group (--COOH), an alkoxycarbonyl group, and an acid halide group. At least one selected from the group consisting of groups, carboxyl groups, alkoxycarbonyl groups, and acid halide groups is more preferred, and at least one selected from the group consisting of cyano groups and carboxyl groups is even more preferred.
- the fluorine-containing elastomer When the fluorine-containing elastomer has the crosslinkable group, it can be reacted with the crosslinking agent of the present disclosure to obtain a crosslinked product having even better heat resistance, plasma resistance, compression set property and crack resistance. be done.
- the fluorine-containing elastomer may have the crosslinkable groups in its main chain and/or side chains.
- the fluorine-containing elastomer is preferably a fluorine-containing elastomer having a cyano group (--CN group) in its main chain and/or side chain.
- a fluorine-containing elastomer having a cyano group (--CN group) in its main chain and/or side chain can be crosslinked by forming an imidazole ring by reacting the cyano group with the amino group of the above compound or the above crosslinking agent. It can impart excellent compression set and heat resistance to molded products.
- fluorine-containing elastomers having cyano groups (--CN groups) in the main chain and/or side chains include perfluoroelastomers and non-perfluoroelastomers.
- the perfluoroelastomer is one in which 90 mol % or more of its structural units are composed of a perfluoromonomer.
- Perfluoroelastomers having cyano groups (--CN groups) in the main chain and/or side chains include those composed of tetrafluoroethylene/perfluoro(alkyl vinyl ether)/monomers having cyano groups (--CN groups). is mentioned.
- the composition of tetrafluoroethylene/perfluoro(alkyl vinyl ether) is preferably 50 to 90/10 to 50 mol%, more preferably 50 to 80/20 to 50 mol%, still more preferably 55 ⁇ 75/25 ⁇ 45 mol%.
- the monomer having a cyano group is 0.1 to 5 mol with respect to the total amount of tetrafluoroethylene and perfluoro(alkyl vinyl ether) from the viewpoint of good cross-linking properties and heat resistance. %, more preferably 0.3 to 3 mol %.
- Perfluoro(alkyl vinyl ether) in this case includes, for example, perfluoro(methyl vinyl ether), perfluoro(propyl vinyl ether) and the like, and these can be used alone or in any combination.
- CF 2 CFOCF 2 CF(CF 3 )OCF 2 CF 2 CN is more preferred.
- perfluoroelastomers include fluororubbers described in International Publication No. 97/24381, Japanese Patent Publication No. 61-57324, Japanese Patent Publication No. 4-81608, Japanese Patent Publication No. 5-13961, etc. is mentioned.
- non-perfluoroelastomers having cyano groups (--CN groups) in the main chain and/or side chains include vinylidene fluoride (VdF)-based fluororubbers, tetrafluoroethylene (TFE)/propylene-based fluororubbers, tetrafluoroethylene ( TFE)/propylene/vinylidene fluoride (VdF)-based fluororubber, ethylene/hexafluoroethylene (HFP)-based fluororubber, ethylene/hexafluoropropylene (HFP)/vinylidene fluoride (VdF)-based fluororubber, ethylene/hexafluoro Propylene (HFP)/tetrafluoroethylene (TFE)-based fluororubber, fluorosilicone-based fluororubber, or fluorophosphazene-based fluororubber may be used, and each of these may be used alone or within
- the vinylidene fluoride-based fluororubber includes 45 to 85 mol% of polymerized units based on vinylidene fluoride and 55 to 15 mol% of polymerized units based on at least one other monomer copolymerizable with vinylidene fluoride.
- a fluorine-containing copolymer consisting of Preferably, a fluorine-containing copolymer consisting of 50 to 80 mol% of polymerized units based on vinylidene fluoride and 50 to 20 mol% of polymerized units based on at least one other monomer copolymerizable with vinylidene fluoride. means coalescence.
- Examples of at least one other monomer copolymerizable with vinylidene fluoride include tetrafluoroethylene (TFE), chlorotrifluoroethylene (CTFE), trifluoroethylene, hexafluoropropylene (HFP), and trifluoropropylene.
- TFE tetrafluoroethylene
- CFE chlorotrifluoroethylene
- HFP hexafluoropropylene
- PAVE perfluoro(alkyl vinyl ether)
- fluorine-containing monomers such as vinyl fluoride, ethylene, propylene, non-fluorine monomers such as alkyl vinyl ether body.
- tetrafluoroethylene, hexafluoropropylene, and perfluoro(alkyl vinyl ether) are preferred.
- Specific rubbers include VdF-HFP rubber, VdF-HFP-TFE rubber, VdF-CTFE rubber, VdF-CTFE-TFE rubber, and the like.
- Tetrafluoroethylene/propylene-based fluororubber is composed of 45 to 70 mol% of polymerized units based on tetrafluoroethylene and 55 to 30 mol% of polymerized units based on propylene, and further polymerized units based on tetrafluoroethylene and polymerized units based on propylene.
- Examples of monomers that provide cross-linking sites include cyano group-containing monomers such as those described in JP-A-4-505345 and JP-A-5-500070, and the above-mentioned general formulas (31) to Examples thereof include the monomer represented by (47).
- These non-perfluoroelastomers can be produced by conventional methods.
- thermoplastic fluorororubber comprising an elastomeric fluoropolymer chain segment and a non-elastomeric fluoropolymer chain segment
- a rubber composition comprising the above fluororubber and a thermoplastic fluororubber may be used.
- a method for isolating the polymerization product from the polymerization reaction mixture a method of coagulating by acid treatment is preferable from the viewpoint of simplification of the process.
- the polymerization mixture may be acid treated and the polymerization product then isolated by means such as freeze-drying.
- methods such as coagulation using ultrasonic waves or the like and coagulation using mechanical force can also be employed.
- the fluorine-containing elastomer preferably has a low metal content.
- a fluorine-containing elastomer having a low metal content is preferable because it provides a molded article that can be used in semiconductor manufacturing processes and pharmaceutical manufacturing processes in which contamination by metal components should be avoided.
- the metal content in the fluorine-containing elastomer is preferably 100 ppm or less, more preferably 50 ppm or less, even more preferably 10 ppm or less.
- the metal content can be measured by flameless atomic absorption spectrometry or high frequency inductively coupled plasma emission spectrometry.
- Metal content in this disclosure is the total metal content of Fe, Cr, Ni, Cu, Al, Na, Mg, Ca, Zn, Ba, and K.
- the amount of the crosslinking agent of the present disclosure is preferably 0.05 to 10 parts by mass, more preferably 0.5 to 5 parts by mass, with respect to 100 parts by mass of the fluorine-containing elastomer. If the cross-linking agent is less than 0.05 parts by mass, the fluorine-containing polymer tends to be insufficiently cross-linked, and if it exceeds 10 parts by mass, the physical properties of the cross-linked product tend to deteriorate.
- cross-linking agents of the present disclosure may be used singly or in combination of two or more. Also, the cross-linking agent of the present disclosure can be used in combination with other compounds. For example, the cross-linking agent of the present disclosure and at least one selected from the group consisting of inorganic nitrides, organic tin compounds, ammonia-generating compounds and cross-linking agents (excluding the cross-linking agent of the present disclosure) are used in combination. You may Crosslinking can be promoted by using these together.
- Examples of the inorganic nitride include, but are not limited to, silicon nitride (Si 3 N 4 ), lithium nitride, titanium nitride, aluminum nitride, boron nitride, vanadium nitride, and zirconium nitride.
- silicon nitride is preferable because nano-sized fine particles can be supplied.
- organic tin compounds examples include tetraphenyltin and triphenyltin.
- a compound that generates ammonia at 40 to 330°C is preferable.
- the ammonia-generating compound is preferably urea or a derivative thereof or an ammonium salt, more preferably urea or an ammonium salt, and still more preferably urea.
- the ammonium salt may be an organic ammonium salt or an inorganic ammonium salt.
- the ammonia-generating compound may react with a trace amount of water to generate ammonia.
- urea derivatives examples include biurea, thiourea, urea hydrochloride, biuret, and the like.
- organic ammonium salt examples include compounds described in JP-A-9-111081, WO 00/09603 and WO 98/23675, such as ammonium perfluorohexanoate and ammonium perfluorooctanoate.
- Ammonium salts of polyfluorocarboxylic acids Ammonium salts of polyfluorosulfonic acids such as ammonium perfluorohexanesulfonate and ammonium perfluorooctane sulfonate; Polyfluoroalkyl groups such as ammonium perfluorohexane phosphate and ammonium perfluorooctane phosphate ammonium salts of contained phosphoric acid or phosphonic acid; ammonium salts of non-fluorinated carboxylic acids or sulfonic acids such as ammonium benzoate, ammonium adipate and ammonium phthalate.
- inorganic ammonium salts examples include compounds described in JP-A-9-111081, such as ammonium sulfate, ammonium carbonate, ammonium nitrate and ammonium phosphate.
- ammonia-generating compounds examples include acetaldehyde ammonia, hexamethylenetetramine, formamidine, formamidine hydrochloride, formamidine acetate, t-butyl carbamate, benzyl carbamate, HCF 2 CF 2 CH(CH 3 )OCONH 2 and phthalamide. etc. are also mentioned.
- cross-linking agent examples include cross-linking agents used in peroxide cross-linking, polyol cross-linking, polyamine cross-linking, triazine cross-linking, oxazole cross-linking, imidazole cross-linking, and thiazole cross-linking.
- the fluorine-containing elastomer is a fluorine-containing elastomer having a cyano group (--CN group)
- the cross-linking agent is preferably at least one selected from the group consisting of an oxazole cross-linking agent, an imidazole cross-linking agent and a thiazole cross-linking agent.
- the cross-linking agent used in peroxide cross-linking may be an organic peroxide that can easily generate peroxy radicals in the presence of heat or a redox system. 5-di(t-butylperoxy)hexane and the like can be used. In general, the type and amount of organic peroxide are selected in consideration of the amount of active --O--O-- and the decomposition temperature.
- the cross - linking aid that can be used in this case may be a compound having a reaction activity with respect to peroxy radicals and polymer radicals.
- triallyl cyanurate triallyl isocyanurate (TAIC)
- triacryl formal triallyl trimellitate, N,N'-n-phenylenebismaleimide, dipropargyl terephthalate, diallyl phthalate, tetraallyl terephthalate amide, triallyl phosphate, bismaleimide, fluorinated triallyl isocyanurate (1,3,5-tris(2,3,3-trifluoro-2-propenyl)-1,3,5-triazine 2,4, 6-trione), tris(diallylamine)-S-triazine, triallyl phosphite, N,N-diallylacrylamide, 1,6-divinyldodecafluorohexane and the like.
- cross-linking aid used together with the peroxide cross-linking agent general formula (48): (wherein the six R 31 are each independently H, a halogen atom, or an optionally halogenated group having 1 to 5 carbon atoms which may be inserted with an ether bond; , Z 31 is a linear or branched optionally halogenated alkylene group of 1 to 18 carbon atoms, cycloalkylene group, or (per)fluoropolyoxy, optionally containing a heteroatom. Alkylene group) can also be mentioned.
- the cross-linking agent or the cross-linking aid used together with the peroxide cross-linking agent has the general formula (52): (wherein R 35 to R 37 are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, or a substituted or unsubstituted aryl group, and at least one of R 35 to R 37 is a fluorine atom or a group containing a fluorine atom, m is an integer of 1 to 5. When m is 2 or more, m R 35 to R 37 are each the same or different A hydrogen atom on the benzene ring may be substituted.) can also be mentioned. When m is 1, it preferably has two or more such structures.
- R 35 to R 37 are as described above, p is an integer of 0 to 2, and n is an integer of 2 to 6
- R 35 to R 37 are as described above.
- R 38 is a single bond, —SO 2 —, —O—, —S—, —CO—, heteroatom-containing group, substituted or unsubstituted an alkylene group, a substituted or unsubstituted cycloalkylene group, or a substituted or unsubstituted arylene group, m is an integer of 1 to 5. These groups may be partially or wholly fluorinated.)
- the compound etc. which are represented by can be mentioned.
- the heteroatom-containing group is not particularly limited as long as it is a divalent group containing a heteroatom.
- heteroatoms include an oxygen atom, a nitrogen atom, a sulfur atom, a boron atom, and a phosphorus atom.
- cross-linking agents used for polyol cross-linking include polyhydric alcohol compounds such as bisphenol A and bisphenol AF.
- Cross-linking agents used for polyamine cross-linking include polyvalent amine compounds such as hexamethylenediamine carbamate, N,N'-dicinnamylidene-1,6-hexanediamine, and 4,4'-bis(aminocyclohexyl)methane carbamate.
- cross-linking agents used for oxazole cross-linking, imidazole cross-linking, and thiazole cross-linking include general formula (55):
- R 41 is —SO 2 —, —O—, —CO—, an alkylene group having 1 to 6 carbon atoms, a perfluoroalkylene group having 1 to 10 carbon atoms, or a single bond, or
- R 42 and R 43 is —NH 2 and the other is —NHR 44 , —NH 2 , —OH or —SH, and R 44 is a hydrogen atom, a fluorine atom or a monovalent an organic group, preferably R 42 is —NH 2 and R 43 is —NHR 44 ; ), a bisdiaminophenyl-based cross-linking agent, a bisaminophenol-based cross-linking agent, and a bisaminothiophenol-based cross-linking agent.
- alkylene group having 1 to 6 carbon atoms include methylene group, ethylene group, propylene group, butylene group, pentylene group, hexylene group and the like. teeth, etc.
- a bisamidrazone-based cross-linking agent represented by the general formula (57): (wherein Rf 41 is a perfluoroalkylene group having 1 to 10 carbon atoms), an amidrazone cross-linking agent represented by the general formula (58): (wherein n is an integer of 1 to 10), general formula (59): HN CR 45 R 46 wherein R 45 is selected from the group consisting of H, NH 2 and NHR 47 and R 46 is the group consisting of Ph, SO 2 H, NR 48 R 49 , 2-pyridine and CH 2 CONH 2 R 47 is selected from the group consisting of Ph, NH 2 and CN; R 48 is H, NHPh, CH 2 CONH 2 , a linear alkyl group having 1 to 8 carbon atoms, and 1 carbon atom is selected from the group consisting of ⁇ 8 branched alkyl groups, and R 49 is Ph, COOC(CH 3 ) 3 , NH 2 , CH 2 COOH, CSNH 2 , CNH
- bisaminophenol-based cross-linking agents bisaminothiophenol-based cross-linking agents, bisdiaminophenyl-based cross-linking agents, and the like have been conventionally used in cross-linking systems with cyano groups as cross-linking points, but carboxyl groups and alkoxycarbonyl It also reacts with a group to form an oxazole ring, thiazole ring, or imidazole ring to give a crosslinked product.
- the above-mentioned cross-linking agent includes general formula (60): X 41 —(CH 2 ) n —R 50 —(CH 2 ) m —X 41 (wherein X 41 is each independently an alkyne group, nitrile group or Y 41 P N 3 (Y 41 is SO, SO 2 , C 6 H 4 or CO, p is 0 or 1), n and m are independently integers of 1 to 4; Yes, R 50 is i) a fluoroalkylene group having 3 to 10 carbon atoms, ii) a fluoroalkoxylylene group having 3 to 10 carbon atoms, iii) a substituted arylene group, iv) oligomers comprising copolymerized units of vinylidene fluoride and perfluoro(methyl vinyl ether), v) oligomers comprising copolymerized units of vinylidene fluoride and hexafluoropropylene; vi) oli
- This cross-linking agent is preferably used together with a fluorine-containing elastomer having a nitrile group, an azide group, a sulfonylazide group, a carbonylazide group or an alkyne group.
- a fluorine-containing elastomer having a nitrile group, an azide group, a sulfonylazide group, a carbonylazide group or an alkyne group.
- the nitrile group of the fluorine-containing elastomer reacts with the azide group of the cross-linking agent to form a tetrazole ring and give a cross-linked product.
- cross-linking agents include compounds having a plurality of 3-amino-4-hydroxyphenyl groups or 3-amino-4-mercaptophenyl groups, or general formula (61):
- 2,2-bis[3-amino-4-(N-phenylamino)phenyl]hexafluoro is used as the cross-linking agent from the viewpoint of heat resistance, steam resistance, amine resistance, and good cross-linking properties.
- Propane is preferred.
- the content of at least one selected from the group consisting of the above inorganic nitrides, organic tin compounds, ammonia-generating compounds and cross-linking agents (excluding the cross-linking agents of the present disclosure) is 100 parts by mass of the fluorine-containing elastomer. , preferably 0.01 to 10 parts by mass, more preferably 0.05 to 5 parts by mass.
- the composition may contain common fillers.
- Examples of the general filler include imide-based fillers having an imide structure such as polyimide, polyamideimide, and polyetherimide; Organic fillers made of engineering plastics such as benzoate, metal oxide fillers such as aluminum oxide, silicon oxide and yttrium oxide, metal carbides such as silicon carbide and aluminum carbide, metal nitride fillers such as silicon nitride and aluminum nitride, aluminum fluoride , fluorocarbon, carbon black, and other inorganic fillers.
- imide-based fillers having an imide structure such as polyimide, polyamideimide, and polyetherimide
- Organic fillers made of engineering plastics such as benzoate, metal oxide fillers such as aluminum oxide, silicon oxide and yttrium oxide, metal carbides such as silicon carbide and aluminum carbide, metal nitride fillers such as silicon nitride and aluminum nitride, aluminum fluoride , fluorocarbon, carbon black, and other inorganic fillers.
- aluminum oxide, yttrium oxide, silicon oxide, polyimide, carbon fluoride, silicon carbide, silicon nitride, and aluminum nitride are preferable from the viewpoint of shielding effect against various plasmas.
- the amount of the general filler compounded is preferably 0.5 to 100 parts by mass, more preferably 5 to 50 parts by mass, per 100 parts by mass of the fluorine-containing elastomer.
- composition can be produced by kneading the compound of the present disclosure or the cross-linking agent of the present disclosure, and the fluorine-containing elastomer.
- kneading can be carried out using ordinary processing machines for polymers, such as open rolls, Banbury mixers, kneaders, internal mixers, and the like.
- the above composition can be suitably used as a molding material for cross-linking molding to obtain a cross-linked product.
- the present disclosure also relates to shaped articles obtained by cross-linking the compositions of the present disclosure.
- the molded article of the present disclosure has excellent plasma resistance while maintaining heat resistance.
- the molded article of the present disclosure can be produced by molding the composition of the present disclosure and crosslinking the resulting molded article, or by simultaneously molding and crosslinking.
- a coating film can also be obtained by applying a crosslinkable composition and crosslinking the composition.
- the molding method is not particularly limited, and examples thereof include compression molding, extrusion molding, transfer molding, injection molding and the like.
- cross-linking conditions are preferably determined according to the type of cross-linking agent used.
- cross-linking is preferably carried out at a temperature of 140 to 300° C. for 1 minute to 24 hours.
- Crosslinking can also be performed under normal pressure, increased pressure, reduced pressure, or in the air.
- the cross-linking method is not particularly limited, and steam cross-linking, pressure molding, and ordinary methods in which a cross-linking reaction is initiated by heating can be employed, and radiation cross-linking at normal temperature and pressure may also be used.
- post-treatment referred to as secondary cross-linking may be performed after the primary cross-linking.
- the primary cross-linking is preferably carried out at 150-250° C. for 5-120 minutes, more preferably at 170-210° C. for 5-60 minutes.
- the cross-linking means a known cross-linking means may be used, and examples thereof include press cross-linking.
- Secondary crosslinking is preferably carried out at 180 to 320° C. for 2 to 24 hours, more preferably at 280 to 310° C. for 5 to 20 hours.
- STEP cross-linking may be used.
- the cross-linking means a known cross-linking means may be used, and examples thereof include oven cross-linking.
- the molded article of the present disclosure has excellent heat resistance, slides in contact with other materials, seals and seals other materials and substances, and is generally used for parts intended for vibration and sound insulation. It can be used as various parts in various fields such as the automobile industry, the aircraft industry, and the semiconductor industry. Fields used include, for example, the semiconductor-related field, the automobile field, the aircraft field, the space/rocket field, the ship field, the chemical field such as chemical plants, the chemical field such as pharmaceuticals, the photographic field such as developing machines, and the printing machinery.
- coating field such as coating equipment, analysis/physical and chemical machinery field such as analytical instruments, instruments, etc.
- food equipment field including food plant equipment and household goods, beverage and food manufacturing equipment field, pharmaceutical manufacturing equipment field, medical parts field, chemistry Chemical transportation equipment field, nuclear power plant equipment field, iron and steel field such as iron plate processing equipment, general industrial field, electrical field, fuel cell field, electronic parts field, optical equipment parts field, space equipment parts field, petrochemical plant equipment field , oil, gas and other energy resource exploration and mining equipment parts fields, petroleum refining fields, petroleum transportation equipment parts fields, and the like.
- Usage forms of the molded article of the present disclosure include, for example, rings, packings, gaskets, diaphragms, oil seals, bearing seals, lip seals, plunger seals, door seals, lip and face seals, gas delivery plate seals, wafer support seals,
- sealing materials such as barrel seals, packing, and the like.
- As a sealing material it can be used in applications requiring heat resistance, solvent resistance, chemical resistance, and non-adhesiveness.
- tubes, hoses, rolls, various rubber rolls, flexible joints, rubber plates, coatings, belts, dampers, valves, valve seats, valve bodies, chemical-resistant coating materials, laminate materials, lining materials, etc. can.
- the cross-sectional shapes of the rings, packings, and seals may be of various shapes. Different shapes such as L-shape, T-shape, V-shape, X-shape, and Y-shape may be used.
- semiconductor manufacturing equipment liquid crystal panel manufacturing equipment, plasma panel manufacturing equipment, plasma display panel manufacturing equipment, plasma addressed liquid crystal panel manufacturing equipment, organic EL panel manufacturing equipment, field emission display panel manufacturing equipment, solar It can be used for battery substrate manufacturing equipment, semiconductor transport equipment, and the like.
- examples of such devices include CVD devices, gas control devices such as gas control devices for semiconductors, dry etching devices, wet etching devices, plasma etching devices, reactive ion etching devices, reactive ion beam etching devices, and sputter etching devices.
- Specific usages in the semiconductor-related field include, for example, gate valves, quartz windows, chambers, chamber lits, gates, bell jars, couplings, O-rings for pumps, gaskets and other sealing materials; resist developer and stripping.
- sealing materials such as O-rings for liquids, hoses and tubes; linings and coatings for resist developer tanks, stripping liquid tanks, wafer cleaning liquid tanks, and wet etching tanks; pump diaphragms; wafer transport rolls; wafer cleaning liquids hose tube; Sealing material for clean equipment such as sealant for clean equipment such as clean room; Sealing material for storing cases such as semiconductor manufacturing equipment and wafers; etc.
- the automobile field also includes motorcycles.
- the molded article of the present disclosure can be used for various sealing materials that require heat resistance, oil resistance, fuel oil resistance, engine cooling antifreeze resistance, and steam resistance.
- sealing materials include seals such as gaskets, shaft seals and valve stem seals, and non-contact or contact type packings such as self-seal packings, piston rings, split ring packings, mechanical seals and oil seals. bellows, diaphragms, hoses, tubes, electric wires, cushioning materials, anti-vibration materials, and various sealing materials used in belt AT devices.
- Line materials such as vapor recovery lines, fuel feed lines, vapor and ORVR lines; Canisters, ORVR, fuel pumps, fuel tank pressure Sensors, gasoline pumps, carburetor sensors, compound air control units (CAC), pulsation dampers, canisters, diaphragms used for auto cocks, pressure regulator diaphragms for fuel injection systems; valves for fuel pumps, carburetor needle valves , rollover check valves, check valves; vents (breathers), tubes used in fuel tanks; tank packings for fuel tanks, etc., packings for acceleration pump pistons of carburetors; fuel sender anti-vibration parts for fuel tanks; O-rings and diaphragms for controlling fuel pressure; accelerator pump cups; in-tank fuel pump mounts; fuel injector injector cushion rings; injector seal rings; valve seats of compound air control devices (CAC); fuel tank bodies; sealing parts
- Specific usage patterns in the above brake system include masterbacks, hydraulic brake hoses, air brakes, diaphragms used in brake chambers of air brakes, etc.; hoses used in brake hoses, brake oil hoses, vacuum brake hoses, etc.; oil seals. , O-rings, packings, brake piston seals, etc.; atmospheric valves and vacuum valves for masterbacks, check valves for brake valves; piston cups (rubber cups) and brake cups for master cylinders; hydraulic brakes master cylinders and vacuum boosters, boots for hydraulic brake wheel cylinders, O-rings and grommets for anti-lock brake systems (ABS).
- ABS anti-lock brake systems
- Specific usages of the above-described basic electrical components include insulators and sheaths for electric wires (harnesses), tubes for harness exterior components, grommets for connectors, and the like. Concrete forms of use in control system electrical components include coating materials for various sensor wires. Specific usages of the above equipment electrical components include car air conditioner O-rings, packing, cooler hoses, high pressure air conditioner hoses, air conditioner hoses, gaskets for electronic throttle units, plug boots for direct ignition, diaphragms for distributors, etc. are mentioned. It can also be used for adhesion of electrical components.
- Specific usages in the intake/exhaust system include packing used for intake manifolds, exhaust manifolds, etc., throttle body packing for throttles; EGR (exhaust gas recirculation), pressure control (BPT), waste gate, turbo waist Diaphragms used for gates, actuators, variable turbine geometry (VTG) turbo actuators, exhaust purification valves, etc.; EGR (exhaust gas recirculation) control hoses, emission control hoses, turbocharger turbo oil hoses (supply), turbos Oil hose (return), turbo air hose, intercooler hose, turbocharger hose, hose connected to compressor of turbo engine with intercooler, exhaust gas hose, air intake hose, turbo hose, DPF (Diesel Particulate Filter) sensor hose air ducts and turbo air ducts; intake manifold gaskets; EGR seals, afterburn prevention valve seats for AB valves, turbine shaft seals (for turbochargers, etc.), and rocker covers and air intakes used
- seals used for steam recovery canisters, catalytic converters, exhaust gas sensors, oxygen sensors, etc., solenoid armature seals for steam recovery and steam canisters, intake system manifold gaskets, etc. can be done.
- it can be used as O-ring seals for direct injection injectors, rotary pump seals, control diaphragms, fuel hoses, EGR, priming pumps, boost compensator diaphragms, etc. in parts related to diesel engines. It can also be used for O-rings, sealing materials, hoses, tubes, diaphragms used in urea SCR systems, urea water tank bodies of urea SCR systems, seal materials for urea water tanks, and the like.
- Transmission-related bearing seals include transmission-related bearing seals, oil seals, O-rings, packings, torque converter hoses, and the like.
- Transmission oil seals, AT transmission oil hoses, ATF hoses, O-rings, packings and the like are also included.
- Transmissions include AT (automatic transmission), MT (manual transmission), CVT (continuously variable transmission), DCT (dual clutch transmission), and the like.
- oil seals, gaskets, O-rings and packings for manual and automatic transmissions oil seals, gaskets, O-rings and packings for continuously variable transmissions (belt type or toroidal type), ATF linear solenoids packing for manual transmissions, oil hoses for manual transmissions, ATF hoses for automatic transmissions, CVTF hoses for continuously variable transmissions (belt type or toroidal type), and the like.
- Specific uses in steering systems include power steering oil hoses and high-pressure power steering hoses.
- Forms used in the engine body of automobile engines include, for example, gaskets such as cylinder head gaskets, cylinder head cover gaskets, oil pan packings, general gaskets, seals such as O-rings, packings, timing belt cover gaskets, control hoses, etc.
- shaft seals such as crankshaft seals and camshaft seals.
- valve systems of automobile engines it can be used for valve stem oil seals of engine valves, valve seats of butterfly valves, and the like.
- radiator hoses In the lubrication and cooling system of automobile engines, engine oil cooler hoses, oil return hoses, seal gaskets for engine oil coolers, water hoses around radiators, radiator seals, radiator gaskets, radiator O-rings, vacuum pumps In addition to vacuum pump oil hoses, it can be used for radiator hoses, radiator tanks, oil pressure diaphragms, fan coupling seals, and the like.
- ⁇ examples of uses in the automotive field include engine head gaskets, oil pan gaskets, manifold packings, oxygen sensor seals, oxygen sensor bushes, nitrogen oxide (NOx) sensor seals, nitrogen oxide (NOx) Sensor bushes, sulfur oxide sensor seals, temperature sensor seals, temperature sensor bushes, diesel particle filter sensor seals, diesel particle filter sensor bushes, injector O-rings, injector packings, fuel pump O-rings and diaphragms, gearboxes seals, power piston packings, cylinder liner seals, valve stem seals, static valve stem seals, dynamic valve stem seals, automatic transmission front pump seals, rear axle pinion seals, universal joint gaskets, speedometer pinion seals, Piston cup of foot brake, O-ring and oil seal of torque transmission device, seal and bearing seal of exhaust gas afterburner, hose for afterburner, diaphragm for carburetor sensor, anti-vibration rubber (engine mount, exhaust part, muffler) hanger, suspension bush, center bearing, stru
- P. S. diaphragms and O-rings gasoline pressure release valves, engine cylinder sleeve O-rings and gaskets, wet cylinder sleeve O-rings and gaskets, differential gear seals and gaskets (gear oil seals and gaskets), power steering devices seals and gaskets (PSF seals and gaskets), shock absorber seals and gaskets (SAF seals and gaskets), constant velocity joint seals and gaskets, wheel bearing seals and gaskets, metal gasket coating agents, caliper seals, Examples include boots, wheel bearing seals, and bladders used in vulcanization molding of tires.
- the space/rocket field, and the ship field it can be used particularly for fuel systems and lubricating oil systems.
- various aircraft seal parts various aircraft parts for aircraft engine oil applications, jet engine valve stem seals, gaskets and O-rings, rotating shaft seals, hydraulic equipment gaskets, firewall seals , fuel supply hoses, gaskets, O-rings, aircraft cables, oil seals, shaft seals, and the like.
- the field of printing such as printing machines
- the field of coating such as coating equipment
- it can be used as rolls, belts, seals, valve parts, etc. of dry copying machines.
- Specific usages in the fields of photography, printing, and coating include surface layers of transfer rolls for copying machines, cleaning blades for copying machines, and belts for copying machines; Rolls (for example, fixing rolls, pressing rolls, pressure rolls, etc.), belts; rolls, roll blades, belts for PPC copiers; rolls for film developing machines and X-ray film developing machines; printing rolls for printing machines , scrapers, tubes, valve parts, belts; ink tubes, rolls, belts for printers; coating rolls, scrapers, tubes, valve parts for coating equipment; developing rolls, gravure rolls, guide rolls, magnetic tape manufacturing coating lines Examples include guide rolls, gravure rolls for magnetic tape manufacturing and coating lines, and coating rolls.
- packings used in products such as alcoholic beverages and soft drinks, filling equipment, food sterilizers, brewing equipment, water heaters, and various automatic food vending machines.
- Specific usages in the above general industrial fields include sealing materials for hydraulic equipment such as machine tools, construction machinery, and hydraulic machinery; seals and bearing seals for hydraulic and lubricating machinery; sealing materials used for mandrels, etc.; dry cleaning equipment.
- Gaskets and sealing materials for equipment used in the papermaking process sealing agents for clean room filter units, building sealing agents, protective coating agents for concrete and cement, glass cloth impregnation materials, processing aids for polyolefin, and molding of polyethylene. It can also be used as a property-improving additive, a fuel container for small generators and lawn mowers, and a pre-coated metal obtained by applying a primer treatment to a metal plate. In addition, it can also be used as a sheet or belt by impregnating a woven fabric and baking it.
- Specific usage patterns in the steel field include iron plate processing rolls for iron plate processing equipment.
- Specific uses in the electrical field include insulating oil caps for bullet trains, venting seals for liquid-sealed transformers, seals for transformers, jackets for oil well cables, seals for ovens such as electric furnaces, and window frames for microwave ovens. Seals, sealing materials used to bond wedges and necks of CRTs, sealing materials for halogen lamps, fixing agents for electrical parts, sealing materials for terminal treatment of sheathed heaters, insulation and moisture-proofing of lead wire terminals of electrical equipment. sealing materials and the like.
- oil-resistant/heat-resistant wires can be used as a coating material for oil-resistant/heat-resistant wires, highly heat-resistant wires, chemical-resistant wires, highly insulated wires, high-voltage transmission wires, cables, wires used in geothermal power generation equipment, wires used around automobile engines, etc. can also It can also be used for oil seals and shaft seals for vehicle cables.
- electrical insulating materials for example, insulating spacers for various electrical equipment, insulating tapes used for cable joints and ends, materials used for heat-shrinkable tubes, etc.
- electrical and electrical materials used in high-temperature atmospheres It can also be used for electronic device materials (for example, lead wire materials for motors, wire materials around high-temperature furnaces). It can also be used as a sealing layer or protective film (back sheet) for solar cells.
- sealing materials between electrodes and between electrodes and separators sealing materials for piping such as hydrogen, oxygen, and generated water, packing, separators etc. can be used.
- binders in the case of electrode active materials in capacitors, sealants, sealants, quartz coating materials for optical fibers, films and sheets such as optical fiber coating materials, electronic parts, Potting, coating, and adhesive seals for circuit boards, fixing agents for electronic components, modifiers for sealants such as epoxy, coating agents for printed circuit boards, modifiers for printed wiring board prepreg resins such as epoxies, scattering prevention materials for light bulbs, etc. , gaskets for computers, cooling hoses for large computers, secondary batteries
- sealing materials used for rotating blowout prevention devices pipe wipers
- sealing materials and gas-liquid connectors used for MWD real-time drilling information detection system
- logging equipment Tool seals (e.g., O-rings, seals, packing, gas-liquid connectors, boots, etc.), expansion packers and completion packers and packer seals used for them, seals and packings used in cementing equipment, perforators (drilling equipment) ), seals and packings used in mud pumps, motor linings, ground hearing detector covers, U-cups, composition seating cups, rotary seals, laminated elastomeric bearings, flow control seals, sand volume control Seals, safety valve seals, fracturing equipment seals, linear packer and linear hanger seals and packings, well head seals and packings, choke and valve seals and packings, LWD (well logging while drilling) diaphragms used in oil exploration/oil drilling applications (for example, lubricating oil supply diaphragms in oil
- joint seals for kitchens, bathrooms, washrooms, etc. cloth for outdoor tents; seals for stamping materials; rubber hoses for gas heat pumps, fluorocarbon-resistant rubber hoses; It can also be used for tanks such as laminated steel plates used in .
- a metal such as aluminum
- usage patterns include door seals, gate valves, pendulum valves, solenoid tips, piston seals and diaphragms bonded to metal, and metal rubber parts bonded to metal such as metal gaskets. It can also be used for rubber parts, brake shoes, brake pads, etc. in bicycles.
- a belt is also included as one of the forms of the molded article of the present disclosure.
- Examples of the belt include the following. Power transmission belts (including flat belts, V-belts, V-ribbed belts, toothed belts, etc.), transport belts (conveyor belts), various high-temperature parts such as around engines of agricultural machinery, machine tools, industrial machinery, etc.
- Conveyor belts for conveying bulk and granular materials such as coal, crushed stone, earth and sand, ores, and wood chips in high-temperature environments; Conveyor belts used in steelworks such as blast furnaces; Conveyor belts for applications exposed to high temperatures in equipment assembly plants, food factories, etc.; agricultural machinery, general equipment (e.g., OA equipment, printing machines, commercial dryers, etc.), V-belts for automobiles, etc. V-ribbed belts; transmission belts for transport robots; toothed belts such as transmission belts for food machinery and machine tools; In particular, timing belts are representative of toothed belts for automobiles.
- the belt may have a single-layer structure or a multi-layer structure.
- the belt may consist of a layer obtained by cross-linking the composition of the present disclosure and a layer of other materials.
- layers made of other materials include layers made of other rubbers, layers made of thermoplastic resin, various fiber reinforcement layers, canvas, metal foil layers, and the like.
- Molded articles of the present disclosure can also be used for industrial anti-vibration pads, anti-vibration mats, railway slab mats, pads, anti-vibration rubber for automobiles, and the like.
- Anti-vibration rubbers for automobiles include anti-vibration rubbers for engine mounts, motor mounts, member mounts, strut mounts, bushes, dampers, muffler hangers, and center bearings.
- joint members such as flexible joints and expansion joints, boots, grommets, and the like.
- a joint member is a joint used in piping and piping equipment.It prevents vibration and noise generated from the piping system, absorbs expansion and contraction and displacement due to temperature and pressure changes, absorbs dimensional fluctuations, earthquakes, and ground subsidence. It is used for purposes such as mitigation and prevention of the effects of Flexible joints and expansion joints are preferably used as complex-shaped moldings for, for example, shipbuilding piping, mechanical piping such as pumps and compressors, chemical plant piping, electrical piping, civil engineering and water piping, and automobiles. can.
- Boots include, for example, constant velocity joint boots, dust covers, rack-and-pinion steering boots, pin boots, piston boots, etc., boots for automobiles, boots for agricultural machinery, boots for industrial vehicles, boots for construction machinery, boots for hydraulic machinery, It can be preferably used as a complex-shaped molding for various industrial boots such as compression machine boots, centralized lubricator boots, liquid transfer boots, firefighting boots, and various liquefied gas transfer boots.
- Molded articles of the present disclosure can also be used for filter press diaphragms, blower diaphragms, water supply diaphragms, liquid storage tank diaphragms, pressure switch diaphragms, accumulator diaphragms, air spring diaphragms such as suspensions, and the like.
- the molded article of the present disclosure can be used as a cushioning material for heat press molding when manufacturing decorative plywood, printed circuit boards, electrical insulating boards, rigid polyvinyl chloride laminates, etc., using melamine resin, phenol resin, epoxy resin, etc. can also be used.
- the molded articles of the present disclosure can also contribute to the impermeability of various substrates such as weapons-related sealing gaskets, protective clothing against contact with aggressive chemical agents, and the like.
- lubricating oils engine oil, mission oil, gear oil, etc.
- amine additives especially amine additives used as antioxidants and detergent dispersants
- O square-rings, V-rings, X-rings, packings, gaskets, diaphragms, oil seals, bearing seals, lip seals used for sealing and sealing oil, fuel oil, and grease (especially urea-based grease)
- plunger seals door seals, lip and face seals
- gas delivery plate seals wafer support seals
- barrel seals and other various sealing materials tubes, hoses, various rubber rolls, coatings, belts, valve bodies of valves etc.
- It can also be used as a laminate material and a lining material.
- the molded article of the present disclosure may be used by forming a vulcanized coating.
- non-adhesive oil resistant rolls for copiers, weather strips for anti-weather anti-freezing, rubber plugs for infusions, aluminum rubber plugs for cases, mold release agents, non-adhesive light transport belts, anti-adhesion coatings for automobile engine mount play gaskets, Uses include coating synthetic fibers, bolt members or joints with a thin layer of packing coating.
- molded product of the present disclosure for automobile-related parts also includes the use of parts for motorcycles having a similar structure.
- fuels related to automobiles include light oil, gasoline, fuels for diesel engines (including biodiesel fuels), and the like.
- composition of the present disclosure can also be used as various parts in various industrial fields, in addition to being crosslinked and used as molded articles. Accordingly, the application of the composition of the present disclosure will now be described.
- the composition of the present disclosure is used for surface-modifying materials such as metals, rubbers, plastics, and glass; sealing materials and covering materials such as metal gaskets and oil seals that require heat resistance, chemical resistance, oil resistance, and non-adhesiveness.
- non-adhesive coating materials such as rolls for OA equipment and belts for OA equipment, or bleed barriers; impregnation on woven fabric sheets and belts, application by baking, and the like.
- the composition of the present disclosure can be used as a sealing material, lining, or sealant with a complicated shape according to normal usage by making it highly viscous and highly concentrated. It can be used for molding and can be used for coating pre-coated metals, O-rings, diaphragms and reed valves by making it medium viscosity. Furthermore, it can also be used for the coating of woven cloth or sheet conveying rolls or belts, printing belts, chemical resistant tubes, chemical plugs, fuel hoses, and the like.
- Article substrates to be coated with the compositions of the present disclosure include metals such as iron, stainless steel, copper, aluminum, and brass; glass products such as glass plates, woven and non-woven fabrics of glass fibers; polypropylene, polyoxymethylene, General-purpose and heat-resistant resin moldings and coatings such as polyimide, polyamideimide, polysulfone, polyethersulfone, and polyetheretherketone; general-purpose rubbers such as SBR, butyl rubber, NBR, and EPDM; Heat-resistant rubber moldings and coatings; woven and non-woven fabrics of natural and synthetic fibers; and the like can be used.
- metals such as iron, stainless steel, copper, aluminum, and brass
- glass products such as glass plates, woven and non-woven fabrics of glass fibers
- General-purpose and heat-resistant resin moldings and coatings such as polyimide, polyamideimide, polysulfone, polyethersulfone, and polyetheretherketone
- Coatings formed from the composition of the present disclosure can be used in fields requiring heat resistance, solvent resistance, lubricity, and non-adhesiveness.
- Rolls e.g., fixing rolls, pressure bonding rolls
- conveyor belts for OA equipment; sheets and belts; O-rings, diaphragms, chemical resistant tubes, fuel hoses, valve seals, chemical plant gaskets, engine gaskets, etc. .
- compositions of the present disclosure can also be dissolved in solvents and used as paints and adhesives. It can also be used as a paint as an emulsified dispersion (latex).
- the above composition is a surface treatment agent for structures composed of inorganic and organic base materials such as sealing materials and linings for various devices and pipes, metals, ceramics, glass, stone, concrete, plastics, rubber, wood, paper, and fibers. etc.
- the above composition can be applied to a substrate or the like by dispenser coating or screen printing.
- compositions of the present disclosure may be used as coating compositions for casting films or impregnating substrates such as fabrics, plastics, metals, or elastomers.
- the compositions of the present disclosure in latex form, can be used in coated fabrics, protective gloves, impregnated fabrics, O-ring coatings, fuel system quick connect O-ring coatings, fuel system seal coatings, fuel tank rollover valve diaphragms. coatings for fuel tank pressure sensor diaphragms; coatings for oil filters and fuel filter seals; coatings for fuel tank sender seals and sender head fitting seals; coatings for copier fuser rolls; may be used. They are useful for coating silicone rubbers, nitrile rubbers, and other elastomers.
- compositions may be applied to exposed cross-sections of multi-layer component structures, for example in methods of making hose structures and diaphragms. Sealing members at connections and joints often consist of hard materials, and the compositions of the present disclosure provide an improved frictional interface, increased dimensional tightness with reduced microleakage along the sealing surface. provide The latex enhances seal durability in various automotive system applications.
- compositions can also be used in the manufacture of power steering systems, fuel systems, air conditioning systems, and any connection where hoses and tubes are connected to another component.
- a further utility of the composition is in repairing manufacturing defects (and damage due to use) in multi-layer rubber constructions such as three-layer fuel hoses.
- the compositions are also useful for coating thin steel sheets that may be formed or embossed before or after the coating is applied. For example, multiple layers of coated steel can be assembled to create a gasket between two rigid metal members. A sealing effect is obtained by applying the composition of the present disclosure between the layers. This process reduces bolt force and strain in the assembled parts, while reducing cracking, deflection, and hole strain for engine head gaskets and exhaust manifold gaskets for the purpose of providing good fuel economy and low emissions. can be used to manufacture
- composition of the present disclosure is used as a coating agent; base-integrated gaskets and packings formed by dispenser molding on a base material containing inorganic materials such as metals and ceramics; It can also be used as a multi-layered article formed by coating.
- 3110 g of the resulting aqueous dispersion was diluted with 3730 g of water and slowly added to 3450 g of a 4.8% by mass nitric acid aqueous solution while stirring. After stirring for 30 minutes after the addition, the coagulate was separated by filtration, and the resulting polymer was thoroughly washed with water and dried in a vacuum to obtain 680 g of a fluorine-containing elastomer.
- the characteristic absorption of the carboxyl group was observed near 1774.9 cm -1 and 1808.6 cm -1, and the characteristic absorption of the OH group was observed near 3557.5 cm -1 and 3095.2 cm -1 . was taken.
- the metal content of the obtained fluorine-containing elastomer was measured using the measuring method described in International Publication No. 94/28394. Specifically, a predetermined amount of a sample containing a metal to be quantified is ashed in a cuvette under ashing conditions including an ashing temperature of about 1000 ° C. and an ashing time of about 240 seconds, and then subjected to flameless atomic absorption as it is. Absorbance was measured with a spectrophotometer. The metal content of the obtained fluorine-containing elastomer was 10 ppm or less.
- the OTf group is a trifluoromethanesulfonate group (CF 3 SO 3 group).
- Synthesis example 1 300 g of toluene, 30 g of Tf, 23.9 g of 3,5-bis(trifluoromethyl)aniline, 39.6 g of cesium carbonate, 3.9 g of palladium acetate, and 14.6 g of triphenylphosphine were added to a 500 ml separable flask in an argon stream. , and refluxed for 16 hours. After cooling, insoluble matter was filtered and toluene was distilled off under reduced pressure. The resulting material was purified by column chromatography to give the following formula with 99% LC purity: 15.0 g (yield 40.6%) of the compound represented by was obtained.
- Synthesis example 2 60 g of Tf compound, 123 g of 2-aminopyridine, 79 g of cesium carbonate, and 720 g of toluene were added to a 1 L separable flask and stirred at room temperature for 2 hours under an argon stream. 13.7 g of triphenylphosphine and 3.9 g of palladium acetate were added, and the temperature was raised to 70°C. After reacting at 70°C for 3 hours, the mixture was cooled to room temperature. After filtration and washing with isopropyl alcohol (IPA), yellow crude crystals were obtained.
- IPA isopropyl alcohol
- Synthesis example 3 30.0 g of Tf compound and 101 g of 2,6-difluoroaniline were added to a 200 ml separable flask and heated to 145°C. After keeping the mixture at 145° C. for 48 hours, 105 g of isopropyl alcohol was added at 70° C., cooled to room temperature, and filtered. After adding isopropyl alcohol and stirring at 70° C. for 30 minutes, the mixture was cooled to room temperature and filtered. After vacuum drying at 70° C. overnight, the following formula with an LC purity of 99.0%: 26.9 g (yield 95.3%) of the compound represented by was obtained.
- Synthesis example 4 80.0 g of Tf compound, 249 g of o-toluidine and 240 g of butyl acetate were added to a 500 ml separable flask, and the mixture was kept under reflux for 1 hour. After cooling, 720.0 g of IPA was added to crystallize, filtered and washed with IPA to obtain orange crystals. This was heated and refluxed with 240 g of isopropyl acetate for 30 minutes, then cooled to room temperature and filtered to obtain yellow crystals. After drying at 50° C. under reduced pressure overnight, the following formula with an LC purity of 98.1%: 53.0 g (yield 75.7%) of the compound represented by was obtained.
- Example 1 The fluorine-containing elastomer obtained in Production Example 1, MT carbon black (manufactured by Cancave, average particle size 0.3 ⁇ m) as a filler, and the compound (crosslinking agent) synthesized in Synthesis Example 2 at a mass ratio of 100/23. /0.8 and kneaded in an open roll to prepare a crosslinkable fluororubber composition.
- This fluororubber composition was pressed at 200° C. for 30 minutes and then heat-treated in an oven at 290° C. for 18 hours to prepare a test sample of O-ring (P24).
- the crosslinkability of the fluororubber composition and the compression set of the test sample were measured by the following methods. Table 1 shows the results.
- compression set compression set, number of cracks
- the compression set of the test sample (O-ring (P24)) was measured according to JIS K6262 at 290° C. after 70 hours, 168 hours, 336 hours and 504 hours.
- the number of cracks when a crack having a length of 10 mm or more was found in the O-ring, it was judged to be cracked, and the number of test samples with cracks was counted.
- Example 2 A sample was prepared in the same manner as in Example 1 except that the cross-linking agent was changed to the compound synthesized in Synthesis Example 3, and cross-linkability and compression set were measured. Table 1 shows the results.
- Example 3 A sample was prepared in the same manner as in Example 1 except that the cross-linking agent was changed to the compound synthesized in Synthesis Example 4, and cross-linkability and compression set were measured. Table 1 shows the results.
- Reference example 1 A sample was prepared in the same manner as in Example 1, except that the cross-linking agent was changed to 2,2-bis[3-amino-4-(N-phenylamino)phenyl]hexafluoropropane (melting point 183° C.). , the compression set was measured. Table 1 shows the results.
- the compound of the present disclosure provides a crosslinked product having good crack resistance while maintaining crosslinkability and heat resistance.
- Examples 4-6 The fluorine-containing elastomer obtained in Production Example 1, the compounds synthesized in Synthesis Examples 2 to 4 as a cross-linking agent, and Si 3 N 4 as a cross-linking accelerator were mixed at a mass ratio of 100/0.8/0.1. They were mixed and kneaded in an open roll to prepare a crosslinkable fluororubber composition. This fluororubber composition was pressed at 180° C. for 30 minutes and then heat-treated in an oven at 290° C. for 18 hours to prepare a test sample of O-ring (P24). The plasma resistance of the above test samples was measured by the following method. Table 2 shows the results.
- the test sample was subjected to oxygen plasma and CF 4 plasma irradiation treatment under the conditions, and the weight loss per unit time was examined.
- Oxygen plasma irradiation conditions Gas flow rate: 16 sccm RF output: 400W Pressure: 2.6Pa Exposure time: 90 minutes, sampling every 15 minutes
- CF4 plasma irradiation conditions Gas flow rate: 16 sccm RF output: 400W Pressure: 2.66Pa Exposure time: 90 minutes, sampling every 15 minutes
- Reference example 2 A test sample was prepared in the same manner as in Examples 4 to 6, except that the cross-linking agent was changed to 2,2-bis[3-amino-4-(N-phenylamino)phenyl]hexafluoropropane, and the plasma resistance was evaluated. evaluated. Table 2 shows the results.
- compositions of the present disclosure provide crosslinked products with good plasma resistance, in particular excellent resistance to oxygen plasma.
- the compound of the present disclosure can be used as a cross-linking agent that provides a cross-linked product with excellent plasma resistance while maintaining heat resistance, or as a monomer for super engineering plastics.
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Abstract
Description
本開示の架橋剤及び組成物は、耐熱性を維持しながら耐プラズマ性に優れた架橋物を与えることができる。
本開示の成形品は、耐熱性を維持しながら耐プラズマ性に優れる。
Aが上記の芳香環基であることにより、上記化合物を架橋剤として使用した際に、架橋物の耐熱性を維持しながら耐プラズマ性(特に耐酸素プラズマ性)を向上させることができる。また、良好な圧縮永久歪特性及び耐クラック性を有する架橋物を得ることもできる。また、Aが上記の芳香環基であることにより、上記化合物の融点を高くすることができ、金型成形の際の金型の汚染を少なくすることができるので、工業上有利である。
上記芳香環は、芳香族炭化水素環又は芳香族複素環であることが好ましい。
なお、上記芳香族炭化水素環を含む芳香環基は、後述する芳香族複素環を含む芳香環基を包含しないものとする。
上記置換基の数は、1~5個であることが好ましく、1~3個であることがより好ましく、1~2個であることが更に好ましい。
上記置換基としては、ハロゲン原子(フッ素原子、塩素原子等)、ハロゲン原子を有していてもよいアルキル基等が挙げられる。上記ハロゲン原子としては、フッ素原子が好ましい。上記アルキル基は、炭素数が1~5であることが好ましく、1~2であることがより好ましく、1であることが更に好ましい。
上記芳香族炭化水素環を含む芳香環基は、-C6H5-mRm(式中、Rはアルキル基、mは1~5の整数)であることも好ましい。
これらの態様において、上記置換基は、一般式(1)においてAが結合する窒素原子に対し、オルト位、メタ位、パラ位のいずれに位置していてもよい。合成の簡便性から、一般式(1)においてAが結合する窒素原子に対し、オルト位又はメタ位に位置していてもよい。
Rfとしての上記フルオロアルキル基は、トリフルオロメチル基であることが好ましい。
Rfは、一般式(1)においてAが結合する窒素原子に対し、オルト位又はメタ位に位置することが好ましい。
nは1~3の整数であることが好ましく、1又は2であることがより好ましく、2であることが更に好ましい。
mは1~3の整数であることが好ましく、1又は2であることがより好ましく、1であることがより好ましい。
上記芳香族複素環を含む芳香環基としては、また、ピリジル基、ピラジニル基、ピリミジニル基、トリアジニル基、キノリル基、キノキサリニル基が好ましく、ピリジル基、ピラジニル基、ピリミジニル基、トリアジニル基がより好ましく、ピリジル基が更に好ましい。
-C6H5-nRfn(式中、Rfはフッ素原子又はフルオロアルキル基、nは1~5の整数)、又は、窒素原子を含む6員の芳香族複素環を含む芳香環基が好ましく、
-C6H5-nRfn(式中、Rfはフッ素原子又は炭素数1~5のフルオロアルキル基、nは1~5の整数)、又は、窒素原子を含む6員の芳香族複素環を含む単環式又は2環式芳香環基がより好ましく、
-C6H5-nRfn(式中、Rfはフッ素原子又は炭素数1~5のフルオロアルキル基、nは1~5の整数)、又は、窒素原子を含む6員の芳香族複素環を含む単環式芳香環基が更に好ましく、
-C6H5-nRfn(式中、Rfはフッ素原子又はトリフルオロメチル基、nは1~5の整数)、ピリジル基、ピラジニル基、ピリミジニル基、又は、トリアジニル基が更により好ましく、
-C6H5-nRfn(式中、Rfはフッ素原子又はトリフルオロメチル基、nは1~5の整数)、又は、ピリジル基が特に好ましい。
-C6H5-mRm(式中、Rはアルキル基、mは1~5の整数)が好ましく、
-C6H5-mRm(式中、Rは炭素数1~5のアルキル基、mは1~5の整数)がより好ましく、
-C6H5-mRm(式中、Rはメチル基(-CH3)、mは1~5の整数)が更に好ましい。
なお、上記アルキル基は置換基を有さない。
上記一般式(1-1)(但し、2つのAは、独立に、置換基を有する6員の芳香族炭化水素環を含む単環式芳香環基、又は、窒素原子又は硫黄原子を含む5員又は6員の芳香族複素環を含む単環式芳香環基である。)で示される化合物がより好ましく、
上記一般式(1-1)(但し、2つのAは、独立に、-C6H5-nRfn(式中、Rfはフッ素原子又はフルオロアルキル基、nは1~5の整数)、-C6H5-mRm(式中、Rはアルキル基、mは1~5の整数)、又は、窒素原子を含む6員の芳香族複素環を含む芳香環基である。)で示される化合物が更に好ましく、
上記一般式(1-1)(但し、2つのAは、独立に、-C6H5-nRfn(式中、Rfはフッ素原子又は炭素数1~5のフルオロアルキル基、nは1~5の整数)、又は、窒素原子を含む6員の芳香族複素環を含む単環式又は2環式芳香環基である。)で示される化合物が更により好ましく、
上記一般式(1-1)(但し、2つのAは、独立に、-C6H5-nRfn(式中、Rfはフッ素原子又は炭素数1~5のフルオロアルキル基、nは1~5の整数)、又は、窒素原子を含む6員の芳香族複素環を含む単環式芳香環基である。)で示される化合物が殊更に好ましく、
上記一般式(1-1)(但し、2つのAは、独立に、-C6H5-nRfn(式中、Rfはフッ素原子又はトリフルオロメチル基、nは1~5の整数)、ピリジル基、ピラジニル基、ピリミジニル基、又は、トリアジニル基である。)で示される化合物が特に好ましい。
上記一般式(1-1)(但し、2つのAは、独立に、-C6H5-mRm(式中、Rは炭素数1~5のアルキル基、mは1~5の整数)である。)で示される化合物がより好ましく、
上記一般式(1-1)(但し、2つのAは、独立に、-C6H5-mRm(式中、Rはメチル基(-CH3)、mは1~5の整数)である。)で示される化合物が更に好ましい。
融点が上記範囲内にあることにより、金型成形の際の金型の汚染を少なくすることができ、工業上有利である。
上記融点は、熱重量示差熱分析装置[TG-DTA]を用いて10℃/minの速度で昇温したときの融解熱曲線における極大値に対応する温度である。
化合物(101)をスルホニル化して、一般式(102):
化合物(102)と一般式(103):
化合物(104)を還元して、上記一般式(1)で示される化合物を得る工程(4)を含む製造方法により好適に製造できる。
R2としては、置換基を有していてもよいアルキル基、置換基を有していてもよいフェニル基が好ましく、メチル基、トリフルオロメチル基、トリル基、ニトロフェニル基がより好ましい。
上記アミンとしては、例えば、トリエチルアミン、トリ(n-プロピル)アミン、トリ(n-ブチル)アミン、ジイソプロピルエチルアミン、シクロヘキシルジメチルアミン、ピリジン、ルチジン、γ-コリジン、N,N-ジメチルアニリン、N-メチルピペリジン、N-メチルピロリジン、N-メチルモルホリン、1,8-ジアザビシクロ[5.4.0]-7-ウンデセン(DBU)、1,5-ジアザビシクロ[4.3.0]-5-ノネン、1,4-ジアザビシクロ[2.2.2]オクタン(DABCO)、4-ジメチルアミノピリジン(DMAP)、プロトンスポンジ等が挙げられる。
上記無機塩基としては、例えば、水酸化リチウム、水酸化カリウム、水酸化ナトリウム、水酸化カルシウム、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸セシウム、炭酸水素セシウム、炭酸水素リチウム、フッ化セシウム、フッ化カリウム、フッ化ナトリウム、塩化リチウム、臭化リチウム等が挙げられる。
上記塩基としては、なかでも、アミンが好ましく、トリエチルアミン、トリブチルアミン、4-ジメチルアミノピリジン(DMAP)、ピリジンがより好ましい。
なかでも、ベンゼン、トルエン、キシレン、ジクロロメタン、クロロホルムが好ましい。
上記ホスフィン配位子が配位した錯体としては、ジクロロ[1,2-ビス(ジフェニルホスフィノ)エタン]パラジウム(II)、
ジクロロ[1,3-ビス(ジフェニルホスフィノ)プロパン]パラジウム(II)、
ジクロロ[1,4-ビス(ジフェニルホスフィノ)ブタン]パラジウム(II)、
ジクロロ[1,5-ビス(ジフェニルホスフィノ)ペンタン]パラジウム(II)、
ジクロロ[ビス(ジフェニルホスフィノフェニル)エーテル]パラジウム(II)、
ジクロロ[ビス(ジシクロヘキシルホスフィノフェニル)エーテル]パラジウム(II)、
ジクロロ[4,5-ビス(ジフェニルホスフィノ)-9,9’-ジメチルキサンテン]パラジウム(II)、
ジクロロ[1,1’-ビス(ジフェニルホスフィノ)フェロセン]パラジウム(II)、
ジクロロ[1,1’-ビス(ジtert-ブチルホスフィノ)フェロセン]パラジウム(II)、
ジクロロ[1,1’-ビス(ジシクロヘキシルホスフィノ)フェロセン]パラジウム(II)、
ジクロロ[1,1’-ビス(ジイソプロピルホスフィノ)フェロセン]パラジウム(II)、
ジクロロ[2,2’‐ビス(ジフェニルホスフィノ)-1,1’-ビナフチル]パラジウム(II)、
ジクロロ[4,6-ビス(ジフェニルホスフィノ)フェノキサジン]パラジウム(II)、
ジクロロ[1,3-ビス(ジイソプロピルホスフィノ)プロパン]パラジウム(II)、
ジクロロ[1,4-ビス(ジイソプロピルホスフィノ)ブタン]パラジウム(II)、
ジクロロ[1,3-ビス(ジシクロヘキシルホスフィノ)プロパン]パラジウム(II)、
ジクロロ[1,4-ビス(ジシクロヘキシルホスフィノ)ブタン]パラジウム(II)
等が挙げられる。
これらのII価パラジウム錯体が、例えば、反応中に共存する還元種(例、ホスフィン、亜鉛、有機金属試薬等)により還元されて、0価パラジウム錯体が生成する。
1)Kanbaraら、Macromolecules、2000年、33巻、657頁
2)Yamamotoら、J.Polym.Sci.、2002年、40巻、2637頁
3)特開平06-32763号公報
4)特開2005-281454号公報
5)特開2009-527352号公報
に示す文献に記載のポリマーホスフィンも利用可能である。
これらの中でも、トリフェニルホスフィン、トリシクロヘキシルホスフィン、トリt-ブチルホスフィンが好ましい。またこれ以外にも、2-ジシクロヘキシルホスフィノ-2’4’6’-トリイソプロピルビフェニル、[4-(N,N-ジメチルアミノ)フェニル]ジ-tert-ブチルホスフィン;並びに4,5-ビス(ジフェニルホスフィノ)-9,9-ジメチル-9H-キサンテン、1,4-ビス(ジフェニルホスフィノ)ブタン、1,3-ビス(ジフェニルホスフィノ)プロパン、1,1’-ビス(ジフェニルホスフィノ)フェロセン、及び2,2’-ビス(ジフェニルホスフィノ)-1,1’-ビナフチルのような二座配位子も有効である。
上記アミンとしては、例えば、トリエチルアミン、トリ(n-プロピル)アミン、トリ(n-ブチル)アミン、ジイソプロピルエチルアミン、シクロヘキシルジメチルアミン、ピリジン、ルチジン、γ-コリジン、N,N-ジメチルアニリン、N-メチルピペリジン、N-メチルピロリジン、N-メチルモルホリン、1,8-ジアザビシクロ[5.4.0]-7-ウンデセン(DBU)、1,5-ジアザビシクロ[4.3.0]-5-ノネン、1,4-ジアザビシクロ[2.2.2]オクタン(DABCO)、4-ジメチルアミノピリジン(DMAP)、プロトンスポンジ等が挙げられる。
上記無機塩基としては、例えば、水酸化リチウム、水酸化カリウム、水酸化ナトリウム、水酸化カルシウム、炭酸リチウム、炭酸ナトリウム、炭酸カリウム、炭酸水素ナトリウム、炭酸水素カリウム、炭酸セシウム、炭酸水素セシウム、炭酸水素リチウム、フッ化セシウム、フッ化カリウム、フッ化ナトリウム、塩化リチウム、臭化リチウム等が挙げられる。
上記有機金属塩基としては、例えば、ブチルリチウム、t-ブチルリチウム、フェニルリチウム、トリフェニルメチルナトリウム、エチルナトリウム等の有機アルカリ金属化合物;メチルマグネシウムブロミド、ジメチルマグネシウム、フェニルマグネシウムクロリド、フェニルカルシウムブロミド、ビス(ジシクロペンタジエン)カルシウム等の有機アルカリ土類金属化合物;ナトリウムメトキシド、t-ブチルメトキシド等のアルコキサイド等が挙げられる。
上記塩基としては、なかでも、炭酸セシウム、炭酸水素セシウム、フッ化セシウム、トリエチルアミン、トリ(n-プロピル)アミン、トリ(n-ブチル)アミン、ピリジン、ルチジン、γ-コリジン、1,8-ジアザビシクロ[5.4.0]-7-ウンデセン(DBU)が好ましい。
なかでも、ベンゼン、トルエン、テトラヒドロフラン、ジオキサン、ジメトキシエタン、ジグライム、酢酸ブチル、N,N-ジメチルホルムアミド、N,N-ジメチルアセトアミド、N-メチルピロリドン、1,3-ジメチル-2-イミダゾリジノンが好ましい。
なお、本開示の化合物を架橋剤として用いる場合、上記一般式(1)における下記式:
フルオロアルキルビニルエーテルとしては、
一般式(8):CF2=CF-ORf81
(式中、Rf81は、炭素数1~8のパーフルオロアルキル基を表す。)で表されるフルオロモノマー、
一般式(10):CF2=CFOCF2ORf101
(式中、Rf101は炭素数1~6の直鎖又は分岐状パーフルオロアルキル基、炭素数5~6の環式パーフルオロアルキル基、1~3個の酸素原子を含む炭素数2~6の直鎖又は分岐状パーフルオロオキシアルキル基である)で表されるフルオロモノマー、及び、
一般式(11):CF2=CFO(CF2CF(Y11)O)m(CF2)nF
(式中、Y11はフッ素原子又はトリフルオロメチル基を表す。mは1~4の整数である。nは1~4の整数である。)で表されるフルオロモノマー
からなる群より選択される少なくとも1種であることが好ましく、一般式(8)で表されるフルオロモノマーがより好ましい。
その組成は、TFE/PMVE共重合体の場合、好ましくは、45~90/10~55(モル%)であり、より好ましくは、55~80/20~45であり、更に好ましくは、55~70/30~45である。
TFE/PMVE/架橋部位を与えるモノマー共重合体の場合、好ましくは、45~89.9/10~54.9/0.01~4(モル%)であり、より好ましくは、55~77.9/20~49.9/0.1~3.5であり、更に好ましくは、55~69.8/30~44.8/0.2~3である。
TFE/炭素数が4~12の一般式(8)、(10)又は(11)で表されるフルオロモノマー共重合体の場合、好ましくは、50~90/10~50(モル%)であり、より好ましくは、60~88/12~40であり、更に好ましくは、65~85/15~35である。
TFE/炭素数が4~12の一般式(8)、(10)又は(11)で表されるフルオロモノマー/架橋部位を与えるモノマー共重合体の場合、好ましくは、50~89.9/10~49.9/0.01~4(モル%)であり、より好ましくは、60~87.9/12~39.9/0.1~3.5であり、更に好ましくは、65~84.8/15~34.8/0.2~3である。
これらの組成の範囲を外れると、ゴム弾性体としての性質が失われ、樹脂に近い性質となる傾向がある。
一般式(12):CX3 2=CX3-Rf 121CHR121X4
(式中、X3は、水素原子、フッ素原子又はCH3、Rf 121は、フルオロアルキレン基、パーフルオロアルキレン基、フルオロ(ポリ)オキシアルキレン基又はパーフルオロ(ポリ)オキシアルキレン基、R121は、水素原子又はCH3、X4は、ヨウ素原子又は臭素原子である)で表されるフルオロモノマー、
一般式(13):CX3 2=CX3-Rf 131X4
(式中、X3は、水素原子、フッ素原子又はCH3、Rf 131は、フルオロアルキレン基、パーフルオロアルキレン基、フルオロポリオキシアルキレン基又はパーフルオロポリオキシアルキレン基、X4は、ヨウ素原子又は臭素原子である)で表されるフルオロモノマー、
一般式(14):CF2=CFO(CF2CF(CF3)O)m(CF2)n-X5
(式中、mは0~5の整数、nは1~3の整数、X5は、シアノ基、カルボキシル基、アルコキシカルボニル基、ヨウ素原子、臭素原子、又は、-CH2Iである)で表されるフルオロモノマー、及び、
一般式(15):CH2=CFCF2O(CF(CF3)CF2O)m(CF(CF3))n-X6
(式中、mは0~5の整数、nは1~3の整数、X6は、シアノ基、カルボキシル基、アルコキシカルボニル基、ヨウ素原子、臭素原子、又は-CH2OHである)で表されるフルオロモノマー、及び、
一般式(16):CR162R163=CR164-Z-CR165=CR166R167
(式中、R162、R163、R164、R165、R166及びR167は、同一又は異なって、水素原子又は炭素数1~5のアルキル基である。Zは、直鎖又は分岐状で酸素原子を有していてもよい、炭素数1~18のアルキレン基、炭素数3~18のシクロアルキレン基、少なくとも部分的にフッ素化している炭素数1~10のアルキレン基若しくはオキシアルキレン基、又は、
-(Q)p-CF2O-(CF2CF2O)m(CF2O)n-CF2-(Q)p-
(式中、Qはアルキレン基又はオキシアルキレン基である。pは0又は1である。m/nが0.2~5である。)で表され、分子量が500~10000である(パー)フルオロポリオキシアルキレン基である。)で表されるモノマー
からなる群より選択される少なくとも1種であることが好ましい。
R13IxBry
(式中、x及びyはそれぞれ0~2の整数であり、かつ1≦x+y≦2を満たすものであり、R13は炭素数1~16の飽和若しくは不飽和のフルオロ炭化水素基又はクロロフルオロ炭化水素基、又は炭素数1~3の炭化水素基であり、酸素原子を含んでいてもよい)で表される化合物が挙げられる。ヨウ素化合物又は臭素化合物を使用することによって、ヨウ素原子又は臭素原子が重合体に導入され、架橋点として機能する。
上記含フッ素エラストマーが上記架橋性基を有するものであると、本開示の架橋剤と反応させることができ、耐熱性、耐プラズマ性、圧縮永久歪特性及び耐クラック性に一層優れる架橋物が得られる。
上記含フッ素エラストマーは、主鎖及び/又は側鎖に上記架橋性基を有してよい。
一般式(31)~(47):
CY1 2=CY1(CF2)n-X1 (31)
(式中、Y1は水素原子又はフッ素原子、nは1~8の整数である)
CF2=CFCF2Rf 2-X1 (32)
(式中、Rf 2は-(OCF2)n-又は-(OCF(CF3))n-であり、nは0~5の整数である)
CF2=CFCF2(OCF(CF3)CF2)m
(OCH2CF2CF2)nOCH2CF2-X1 (33)
(式中、mは0~5の整数、nは0~5の整数である)
CF2=CFCF2(OCH2CF2CF2)m
(OCF(CF3)CF2)nOCF(CF3)-X1 (34)
(式中、mは0~5の整数、nは0~5の整数である)
CF2=CF(OCF2CF(CF3))mO(CF2)n-X1 (35)
(式中、mは0~5の整数、nは1~8の整数である)
CF2=CF(OCF2CF(CF3))m-X1 (36)
(式中、mは1~5の整数)
CF2=CFOCF2(CF(CF3)OCF2)nCF(-X1)CF3 (37)
(式中、nは1~4の整数)
CF2=CFO(CF2)nOCF(CF3)-X1 (38)
(式中、nは2~5の整数)
CF2=CFO(CF2)n-(C6H4)-X1 (39)
(式中、nは1~6の整数)
CF2=CF(OCF2CF(CF3))nOCF2CF(CF3)-X1 (40)
(式中、nは1~2の整数)
CH2=CFCF2O(CF(CF3)CF2O)nCF(CF3)-X1 (41)
(式中、nは0~5の整数)、
CF2=CFO(CF2CF(CF3)O)m(CF2)n-X1 (42)
(式中、mは0~5の整数、nは1~3の整数である)
CH2=CFCF2OCF(CF3)OCF(CF3)-X1 (43)
CH2=CFCF2OCH2CF2-X1 (44)
CF2=CFO(CF2CF(CF3)O)mCF2CF(CF3)-X1 (45)
(式中、mは0以上の整数である)
CF2=CFOCF(CF3)CF2O(CF2)n-X1 (46)
(式中、nは1以上の整数)
CF2=CFOCF2OCF2CF(CF3)OCF2-X1 (47)
(一般式(31)~(47)中、X1は、シアノ基(-CN基)である)で表される単量体等が挙げられ、これらをそれぞれ単独で、又は任意に組み合わせて用いることができる。
上記含フッ素エラストマー中の金属含有量は100ppm以下であることが好ましく、50ppm以下であることがより好ましく、10ppm以下であることが更に好ましい。
上記金属含有量は、フレームレス原子吸光分析法又は高周波誘導結合プラズマ発光分光分析法により測定することができる。本開示における金属含有量は、Fe、Cr、Ni、Cu、Al、Na、Mg、Ca、Zn、Ba、及びKの合計の金属含有量である。
また、本開示の架橋剤と他の化合物とを併用することもできる。例えば、本開示の架橋剤と、無機窒化物、有機スズ化合物、アンモニアを発生させる化合物及び架橋剤(但し、本開示の架橋剤を除く。)からなる群より選択される少なくとも1種とを併用してもよい。これらを併用することで架橋促進が可能である。
(式中、R45は、H、NH2、及びNHR47からなる群から選択され、R46は、Ph、SO2H、NR48R49、2-ピリジン、及びCH2CONH2からなる群から選択され、R47は、Ph、NH2、及びCNからなる群から選択され、R48は、H、NHPh、CH2CONH2、炭素数1~8の直鎖アルキル基、及び炭素数1~8の分枝アルキル基からなる群から選択され、かつ、R49は、Ph、COOC(CH3)3、NH2、CH2COOH、CSNH2、CNHNH3 +Cl-、p-フェニルCN、
i)炭素数3~10のフルオロアルキレン基、
ii)炭素数3~10のフルオロアルコキシレン基、
iii)置換アリーレン基、
iv)フッ化ビニリデン及びパーフルオロ(メチルビニルエーテル)の共重合単位を含むオリゴマー、
v)フッ化ビニリデン及びヘキサフルオロプロピレンの共重合単位を含むオリゴマー、
vi)テトラフルオロエチレン及びパーフルオロ(メチルビニルエーテル)の共重合単位を含むオリゴマー、並びに、
vii)テトラフルオロエチレン及び炭化水素オレフィンの共重合単位を含むオリゴマーからなる群から選択される)で表される架橋剤を挙げることもできる。この架橋剤は、ニトリル基、アジド基、スルホニルアジド基、カルボニルアジド基又はアルキン基を有する含フッ素エラストマーとともに用いることが好ましい。例えば、含フッ素エラストマーのニトリル基と、架橋剤のアジド基とが反応して、テトラゾール環を形成し、架橋物を与える。
用いられる分野としては例えば、半導体関連分野、自動車分野、航空機分野、宇宙・ロケット分野、船舶分野、化学プラント等の化学品分野、医薬品等の薬品分野、現像機等の写真分野、印刷機械等の印刷分野、塗装設備等の塗装分野、分析機器、計器等の分析・理化学機械分野、食品プラント機器及び家庭用品を含む食品機器分野、飲料食品製造装置分野、医薬品製造装置分野、医療部品分野、化学薬品輸送用機器分野、原子力プラント機器分野、鉄板加工設備等の鉄鋼分野、一般工業分野、電気分野、燃料電池分野、電子部品分野、光学機器部品分野、宇宙用機器部品分野、石油化学プラント機器分野、石油、ガス等のエネルギー資源探索採掘機器部品分野、石油精製分野、石油輸送機器部品分野等が挙げられる。
また、チューブ、ホース、ロール、各種ゴムロール、フレキシブルジョイント、ゴム板、コーティング、ベルト、ダンパー、バルブ、バルブシート、バルブの弁体、耐薬品用コーティング材料、ラミネート用材料、ライニング用材料等としても使用できる。
なお、上記リング、パッキン、シールの断面形状は、種々の形状のものであってよく、具体的には、例えば、四角、O字、へルール等の形状であってもよいし、D字、L字、T字、V字、X字、Y字等の異形状であってもよい。
上述のようなエンジン本体やその周辺装置では、耐熱性、耐油性、燃料油耐性、エンジン冷却用不凍液耐性、耐スチーム性が要求される各種シール材に本開示の成形品を用いることができ、そのようなシール材としては、例えば、ガスケット、シャフトシール、バルブステムシール等のシールや、セルフシールパッキン、ピストンリング、割リング形パッキン、メカニカルシール、オイルシール等の非接触型又は接触型のパッキン類、ベローズ、ダイアフラム、ホース、チューブの他、電線、緩衝材、防振材、ベルトAT装置に用いられる各種シール材等が挙げられる。
制御系電装部品における具体的な使用形態としては、各種センサー線の被覆材料等が挙げられる。
上記装備電装部品における具体的な使用形態としては、カーエアコンのO-リング、パッキンや、クーラーホース、高圧エアコンホース、エアコンホース、電子スロットルユニット用ガスケット、ダイレクトイグニッション用プラグブーツ、ディストリビューター用ダイアフラム等が挙げられる。また、電装部品の接着にも用いることができる。
また、ディーゼルエンジンに関する部品において、直噴インジェクター用のO-リングシール、回転ポンプシール、制御ダイアフラム、燃料ホース、EGR,プライミングポンプ,ブーストコンペンセーターのダイアフラム等として用いることができる。また、尿素SCRシステムに用いられるO-リング、シール材、ホース、チューブ、ダイアフラムや、尿素SCRシステムの尿素水タンク本体、及び尿素水タンクのシール材等にも用いることができる。
ミッションオイルシールや、ATのミッションオイルホース、ATFホース、O-リング、パッキン類等も挙げられる。
なお、トランスミッションには、AT(オートマチック・トランスミッション)、MT(マニュアル・トランスミッション)、CVT(連続可変トランスミッション)、DCT(デュアル・クラッチ・トランスミッション)等がある。
また、手動又は自動変速機用のオイルシール、ガスケット、O-リング、パッキンや、無段変速機(ベルト式又はトロイダル式)用のオイルシール、ガスケット、O-リング、パッキンの他、ATFリニアソレノイド用パッキング、手動変速機用オイルホース、自動変速機用ATFホース、無断変速機(ベルト式又はトロイダル式)用CVTFホース等も挙げられる。
ステアリング系における具体的な使用形態としては、パワーステアリングオイルホースや高圧パワーステアリングホース等が挙げられる。
自動車エンジンの主運動系においては、クランクシャフトシール、カムシャフトシール等のシャフトシール等に用いることができる。
自動車エンジンの動弁系においては、エンジンバルブのバルブステムオイルシール、バタフライバルブのバルブシート等に用いることができる。
自動車エンジンの潤滑・冷却系においては、エンジンオイルクーラーのエンジンオイルクーラーホース、オイルリターンホース、シールガスケットや、ラジエータ周辺のウォーターホース、ラジエータのシール、ラジエータのガスケット、ラジエータのO-リング、バキュームポンプのバキュームポンプオイルホース等の他、ラジエーターホース、ラジエータータンク、オイルプレッシャー用ダイアフラム、ファンカップリングシール等に用いることができる。
上記航空機分野においては、例えば、航空機用各種シール部品、航空機用エンジンオイル用途の航空機用各種部品、ジェットエンジンバルブステムシールやガスケットやO-リング、ローテーティングシャフトシール、油圧機器のガスケット、防火壁シール、燃料供給用ホースやガスケットやO-リング、航空機用ケーブルやオイルシールやシャフトシール等として用いることが可能である。
また、船舶分野においては、例えば、スクリューのプロペラシャフト船尾シール、ディーゼルエンジンの吸排気用バルブステムシール、バタフライバルブのバルブシール、バタフライバルブのバルブシートや軸シール、バタフライ弁の軸シール、船尾管シール、燃料ホース、ガスケット、エンジン用のO-リング、船舶用ケーブル、船舶用オイルシール、船舶用シャフトシール等として使用することができる。
上記化学品分野及び薬品分野における具体的な使用形態としては、化学装置、化学薬品用ポンプや流量計、化学薬品用配管、熱交換器、農薬散布機、農薬移送ポンプ、ガス配管、燃料電池、分析機器や理化学機器(例えば、分析機器や計器類のカラム・フィッティング等)、排煙脱硫装置の収縮継ぎ手、硝酸プラント、発電所タービン等に用いられるシールや、医療用滅菌プロセスに用いられるシール、メッキ液用シール、製紙用ベルトのコロシール、風洞のジョイントシール;反応機、攪拌機等の化学装置、分析機器や計器類、ケミカルポンプ、ポンプハウジング、バルブ、回転計等に用いられるO-リングや、メカニカルシール用O-リング、コンプレッサーシーリング用のO-リング;高温真空乾燥機、ガスクロマトグラフィーやpHメーターのチューブ結合部等に用いられるパッキンや、硫酸製造装置のガラス冷却器パッキン;ダイアフラムポンプ、分析機器や理化学機器等に用いられるダイアフラム;分析機器、計器類に用いられるガスケット;分析機器や計器類に用いられるはめ輪(フェルール);バルブシート;Uカップ;化学装置、ガソリンタンク、風洞等に用いられるライニングや、アルマイト加工槽の耐食ライニング;メッキ用マスキング冶具のコーティング;分析機器や理化学機器の弁部品;排煙脱硫プラントのエキスパンジョンジョイント;濃硫酸等に対する耐酸ホース、塩素ガス移送ホース、耐油ホース、ベンゼンやトルエン貯槽の雨水ドレンホース;分析機器や理化学機器等に用いられる耐薬品性チューブや医療用チューブ;繊維染色用の耐トリクレン用ロールや染色用ロール;医薬品の薬栓;医療用のゴム栓;薬液ボトル、薬液タンク、バッグ、薬品容器;耐強酸、耐溶剤の手袋や長靴等の保護具等が挙げられる。
上記写真分野、印刷分野及び塗装分野における具体的な使用形態としては、複写機の転写ロールの表面層、複写機のクリーニングブレード、複写機のベルト;複写機、プリンター、ファクシミリ等のOA機器用のロール(例えば、定着ロール、圧着ロール、加圧ロール等が挙げられる。)、ベルト;PPC複写機のロール、ロールブレード、ベルト;フィルム現像機、X線フィルム現像機のロール;印刷機械の印刷ロール、スクレーパー、チューブ、弁部品、ベルト;プリンターのインキチューブ、ロール、ベルト;塗布、塗装設備の塗装ロール、スクレーパー、チューブ、弁部品;現像ロール、グラビアロール、ガイドロール、磁気テープ製造塗工ラインのガイドロール、磁気テープ製造塗工ラインのグラビアロール、コーティングロール等が挙げられる。
上記食品機器分野における具体的な使用形態としては、プレート式熱交換器のシール、自動販売機の電磁弁シール、ジャーポットのパッキン、サニタリーパイプパッキン、圧力鍋のパッキン、湯沸器シール、熱交換器用ガスケット、食品加工処理装置用のダイアフラムやパッキン、食品加工処理機用ゴム材料(例えば、熱交換器ガスケット、ダイアフラム、O-リング等の各種シール、配管、ホース、サニタリーパッキン、バルブパッキン、充填時にビン等の口と充填剤との間のジョイントとして使用される充填用パッキン)等が挙げられる。また、酒類、清涼飲料水等の製品、充填装置、食品殺菌装置、醸造装置、湯沸し器、各種自動食品販売機等に用いられるパッキン、ガスケット、チューブ、ダイアフラム、ホース、ジョイントスリーブ等も挙げられる。
上記エネルギー資源探索採掘機器部品分野における具体的な使用形態としては、ドリルビットシール、圧力調整ダイアフラム、水平掘削モーター(ステーター)のシール、ステーターベアリング(シャフト)シール、暴噴防止装置(BOP)に用いられるシール材、回転暴噴防止装置(パイプワイパー)に用いられるシール材、MWD(リアルタイム掘削情報探知システム)に用いられるシール材や気液コネクター、検層装置(ロギングエクイップメント)に用いられる検層ツールシール(例えば、O-リング、シール、パッキン、気液コネクター、ブーツ等)、膨張型パッカーやコンプリーションパッカー及びそれらに用いるパッカーシール、セメンチング装置に用いられるシールやパッキン、パーフォレーター(穿孔装置)に用いられるシール、マッドポンプに用いられるシールやパッキンやモーターライニング、地中聴検器カバー、Uカップ、コンポジションシーティングカップ、回転シール、ラミネートエラストメリックベアリング、流量制御のシール、砂量制御のシール、安全弁のシール、水圧破砕装置(フラクチャリングエクイップメント)のシール、リニアーパッカーやリニアーハンガーのシールやパッキン、ウェルヘッドのシールやパッキン、チョークやバルブのシールやパッキン、LWD(掘削中検層)用シール材、石油探索・石油掘削用途で用いられるダイアフラム(例えば、石油掘削ピット等の潤滑油供給用ダイアフラム)、ゲートバルブ、電子ブーツ、穿孔ガンのシールエレメント等が挙げられる。
また、自転車におけるゴム部品、ブレーキシュー、ブレーキパッド等にも用いることができる。
特に、自動車用歯付きベルトとしては、タイミングベルトが代表的である。
多層構造である場合、上記ベルトは、本開示の組成物を架橋して得られる層及び他の材料からなる層からなるものであってもよい。
多層構造のベルトにおいて、他の材料からなる層としては、他のゴムからなる層や熱可塑性樹脂からなる層、各種繊維補強層、帆布、金属箔層等が挙げられる。
ジョイント部材とは、配管及び配管設備に用いられる継ぎ手のことであり、配管系統から発生する振動、騒音の防止、温度変化、圧力変化による伸縮や変位の吸収、寸法変動の吸収や地震、地盤沈下による影響の緩和、防止等の用途に用いられる。
フレキシブルジョイント、エキスパンションジョイントは、例えば、造船配管用、ポンプやコンプレッサー等の機械配管用、化学プラント配管用、電気配管用、土木・水道配管用、自動車用等の複雑形状成形体として好ましく用いることができる。
ブーツは、例えば、等速ジョイントブーツ、ダストカバー、ラックアンドピニオンステアリングブーツ、ピンブーツ、ピストンブーツ等の自動車用ブーツ、農業機械用ブーツ、産業車両用ブーツ、建築機械用ブーツ、油圧機械用ブーツ、空圧機械用ブーツ、集中潤滑機用ブーツ、液体移送用ブーツ、消防用ブーツ、各種液化ガス移送用ブーツ等の各種産業用ブーツ等の複雑形状成形体として好ましく用いることができる。
また、上記自動車関連における燃料としては、軽油、ガソリン、ディーゼルエンジン用燃料(バイオディーゼルフューエルを含む)等が挙げられる。
本開示の組成物は、金属、ゴム、プラスチック、ガラス等の表面改質材;メタルガスケット、オイルシール等、耐熱性、耐薬品性、耐油性、非粘着性が要求されるシール材及び被覆材;OA機器用ロール、OA機器用ベルト等の非粘着被覆材、又はブリードバリヤー;織布製シート及びベルトへの含浸、焼付による塗布等に用いることができる。
本開示の組成物は、高粘度、高濃度にすることによって、通常の用法により複雑な形状のシール材、ライニング、シーラントとして用いることができ、低粘度にすることによって、数ミクロンの薄膜フィルムの形成に用いることができ、また中粘度にすることによりプレコートメタル、O-リング、ダイアフラム、リードバルブの塗布に用いることができる。
更に、織布や紙葉の搬送ロール又はベルト、印刷用ベルト、耐薬品性チューブ、薬栓、ヒューエルホース等の塗布にも用いることができる。
本開示の組成物から形成される被覆物は、耐熱性、耐溶剤性、潤滑性、非粘着性が要求される分野で使用でき、具体的な用途としては、複写機、プリンター、ファクシミリ等のOA機器用のロール(例えば、定着ロール、圧着ロール)及び搬送ベルト;シート及びベルト;O-リング、ダイアフラム、耐薬品性チューブ、燃料ホース、バルブシール、化学プラント用ガスケット、エンジンガスケット等が挙げられる。
上記組成物は、各種装置、配管等のシール材やライニング、金属、セラミックス、ガラス、石、コンクリート、プラスチック、ゴム、木材、紙、繊維等の無機及び有機基材からなる構造物の表面処理剤等として使用される。
上記組成物は、ディスペンサー方式塗装やスクリーン印刷塗装により基材等に塗布することができる。
特に、本開示の組成物は、ラテックスの形態として、被覆ファブリック、保護手袋、含浸繊維、O-リング被覆、燃料系クイック連結O-リング用被覆、燃料系シール用被覆、燃料タンクロールオーバーバルブダイヤフラム用被覆、燃料タンク圧力センサーダイヤフラム用被覆、オイルフィルター及び燃料フィルターシール用被覆、燃料タンクセンダーシール及びセンダーヘッドフィッテングシール用被覆、複写機定着機構ロール用被覆、並びにポリマー塗料組成物を製造するために使用されてもよい。
それらはシリコーンラバー、ニトリルラバー、及び他のエラストマーの被覆に有用である。その熱安定性と同様に基材エラストマーの耐透過性及び耐薬品性の両方を高める目的のために、それらはそのようなエラストマーから製造される部品の被覆にも有用である。他の用途は、熱交換器、エキスパンジョンジョイント、バット、タンク、ファン、煙道ダクト及び他の管路、並びに収納構造体、例えばコンクリート収納構造体用の被覆を含む。上記組成物は、多層部品構造の露出した断面に、例えばホース構造及びダイアフラムの製造方法において塗布されてもよい。接続部及び結合部におけるシーリング部材は、硬質材料からしばしば成り、そして本開示の組成物は、改良された摩擦性界面、シーリング面に沿って低減された微量の漏れを伴う高められた寸法締りばめを提供する。そのラテックスは、種々の自動車システム用途におけるシール耐久性を高める。
それらは、パワーステアリング系統、燃料系統、エアーコンディショニング系統、並びに、ホース及びチューブが別の部品に接続されるいかなる結合部の製造においても使用されることもできる。上記組成物のさらなる有用性は、3層燃料ホースのような多層ラバー構造における、製造欠陥(及び使用に起因する損傷)の補修においてである。上記組成物は、塗料が塗布される前又は後に、形成され、又はエンボス加工され得る薄鋼板の塗布にも有用である。例えば、被覆された鋼の多数の層は組み立てられて、2つの剛性金属部材の間にガスケットを作ることもできる。シーリング効果は、その層の間に本開示の組成物を塗布することにより得られる。このプロセスは、組み立てられた部品のボルト力及びひずみを低下させ、一方、低い亀裂、たわみ、及び穴ひずみにより良好な燃料節約及び低放出を提供する目的のために、エンジンヘッドガスケット及び排気マニホールドガスケットを製造するために使用され得る。
国際公開第2020/026909号の製造例1に倣って、TFE/PMVE/CF2=CFOCF2CF(CF3)OCF2CF2CN(CNVE)共重合体の水性分散液を得た。
500mlセパラブルフラスコにアルゴン気流中トルエン300g、Tf体30g、3,5-ビス(トリフルオロメチル)アニリン23.9g、炭酸セシウム39.6g、酢酸パラジウム3.9g、トリフェニルホスフィン14.6gを加え、16時間還流させた。冷却後に不溶物をろ過し、トルエンを減圧留去した。得られた物質をカラムクロマトグラフィーで精製し、LC純度99%の下記式:
1LセパラブルフラスコにTf体60g、2-アミノピリジン123g、炭酸セシウム79g、トルエン720gを加えて、アルゴン気流過下、室温で2時間撹拌した。トリフェニルホスフィン13.7g及び酢酸パラジウム3.9gを加え、70℃まで昇温した。70℃、3時間反応後、室温まで冷却した。ろ過を行い、イソプロピルアルコール(IPA)で洗浄し黄色の粗結晶を得た。メタノール180gを加え30分の加熱還流後、室温まで冷却後にろ過を行い、イオン交換水で洗浄した。70℃で乾燥を一晩行い、LC純度99%の下記式:
200mlセパラブルフラスコにTf体30.0gと2,6-ジフルオロアニリン101gを加えて145℃まで昇温した。145℃で48時間保温した後、70℃でイソプロピルアルコールを105g加え、室温まで冷却後にろ過をした。イソプロピルアルコールを加え70℃で30min撹拌した後、室温まで冷却しろ過をした。70℃で減圧乾燥を一晩行い、LC純度99.0%の下記式:
500mlセパラブルフラスコにTf体80.0g、o-トルイジン249g、酢酸ブチル240gを加えて、還流下1時間保温した。冷却後にIPA720.0gを加えて晶析させ、ろ過及びIPA洗浄し、橙色結晶を得た。これに酢酸イソプロピル240gで加熱・還流30分行った後、室温まで冷却、ろ過をして黄色結晶を得た。50℃、減圧乾燥を一晩行い、LC純度98.1%の下記式:
製造例1で得られた含フッ素エラストマーと、充填剤であるMTカーボンブラック(キャンキャーブ製、平均粒子径0.3μm)と、合成例2で合成した化合物(架橋剤)とを質量比100/23/0.8で混合し、オープンロールにて混練して架橋可能なフッ素ゴム組成物を調製した。このフッ素ゴム組成物を200℃で30分間プレスしたのち、更にオーブン中で290℃で18時間の加熱処理を施し、O-リング(P24)の被験サンプルを作製した。上記フッ素ゴム組成物について架橋性を、上記被験サンプルについて圧縮永久歪を、それぞれ以下の方法により測定した。結果を表1に示す。
上記フッ素ゴム組成物について、アルファテクノロジーズ社製ラバープロセスアナライザー2000を用いて、200℃、30分、周波数1Hz、歪み10%の条件で加硫特性を測定し、G’最大値及び適正加硫時間(Т90)を求めた。
上記被験サンプル(O-リング(P24))について、JIS K6262に準じて、290℃下で、70時間後、168時間後、336時間後、504時間後の圧縮永久歪を測定した。割れ数は、O-リングに長さ10mm以上のクラックが見られた場合、割れと判断し、割れの生じた被験サンプルの数をカウントした。
架橋剤を合成例3で合成した化合物に変更した以外は、実施例1と同様に試料を作製し、架橋性、圧縮永久歪を測定した。結果を表1に示す。
架橋剤を合成例4で合成した化合物に変更した以外は、実施例1と同様に試料を作製し、架橋性、圧縮永久歪を測定した。結果を表1に示す。
架橋剤を2,2-ビス[3-アミノ―4-(N-フェニルアミノ)フェニル]ヘキサフルオロプロパン(融点183℃)に変更した以外は、実施例1と同様に試料を作製し、架橋性、圧縮永久歪を測定した。結果を表1に示す。
実施例1~3及び参考例1で作製した被験サンプルを350℃、21時間加熱した。
加熱前及び加熱後のサンプルをフッ素系溶剤R-318(ダイキン工業株式会社製)に23℃、96時間の条件で浸漬し、加熱後/加熱前の膨潤比を測定した。この値が小さいほど耐熱性が高いことを意味する。結果を表1に示す。
製造例1で得られた含フッ素エラストマーと、架橋剤としての合成例2~4で合成した化合物と、架橋促進剤としてのSi3N4とを質量比100/0.8/0.1で混合し、オープンロールにて混練して架橋可能なフッ素ゴム組成物を調製した。このフッ素ゴム組成物を180℃で30分間プレスしたのち、更にオーブン中で290℃で18時間の加熱処理を施し、O-リング(P24)の被験サンプルを作製した。
上記被験サンプルについて、耐プラズマ性を以下の方法により測定した。結果を表2に示す。
被験サンプルに条件下で酸素プラズマ及びCF4プラズマ照射処理を行い、単位時間あたりの重量減少を調べた。
酸素プラズマ照射条件:
ガス流量:16sccm
RF出力:400W
圧力:2.6Pa
曝露時間:90分間、15分毎にサンプリング
CF4プラズマ照射条件:
ガス流量:16sccm
RF出力:400W
圧力:2.66Pa
曝露時間:90分間、15分毎にサンプリング
架橋剤を2,2-ビス[3-アミノ―4-(N-フェニルアミノ)フェニル]ヘキサフルオロプロパンに変えた以外は、実施例4~6と同様に被験サンプルを作製し、耐プラズマ性を評価した。結果を表2に示す。
Claims (8)
- 前記芳香環基は、置換基を有する6員の芳香族炭化水素環を含む単環式芳香環基、又は、窒素原子又は硫黄原子を含む5員又は6員の芳香族複素環を含む単環式芳香環基である請求項1記載の化合物。
- 前記芳香環基は、ベンゼン環よりもπ電子欠乏性を示す基である請求項1又は2記載の化合物。
- 前記置換基が、ハロゲン原子及びハロゲン原子を有していてもよいアルキル基からなる群より選択される少なくとも1種である請求項1~3のいずれかに記載の化合物。
- 請求項1~4のいずれかに記載の化合物を含む架橋剤。
- 含フッ素エラストマーと、請求項1~4のいずれかに記載の化合物又は請求項5記載の架橋剤とを含む組成物。
- 前記含フッ素エラストマーが架橋性基を有しており、前記架橋性基が、ヒドロキシ基(-OH)、シアノ基(-CN)、カルボキシル基(-COOH)、アルコキシカルボニル基、及び酸ハライド基からなる群より選択される少なくとも1種である請求項6記載の組成物。
- 請求項6又は7記載の組成物を架橋して得られる成形品。
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