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WO2007032310A1 - Élastomère fluoré, procédé de production d'élastomère fluoré et composé contenant du silicium - Google Patents

Élastomère fluoré, procédé de production d'élastomère fluoré et composé contenant du silicium Download PDF

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Publication number
WO2007032310A1
WO2007032310A1 PCT/JP2006/317978 JP2006317978W WO2007032310A1 WO 2007032310 A1 WO2007032310 A1 WO 2007032310A1 JP 2006317978 W JP2006317978 W JP 2006317978W WO 2007032310 A1 WO2007032310 A1 WO 2007032310A1
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group
fluorine
chemical
functional group
compound
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Japanese (ja)
Inventor
Tatsuya Morikawa
Meiten Koh
Tetsuo Shimizu
Masayuki Hayashi
Tadashi Okawa
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Daikin Industries Ltd
DuPont Toray Specialty Materials KK
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Daikin Industries Ltd
Dow Corning Toray Co Ltd
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  • Fluorine-containing elastomer Method for producing fluorine-containing elastomer, and key compound-containing compound
  • the present invention relates to a method for producing a crosslinkable fluorine-containing elastomer containing a specific functional group at the main chain end and Z or side chain end, and a fluorine-containing elastomer obtained by the production method.
  • the present invention relates to a curable composition that also has the power of the fluorine-containing elastomer and a molded product obtained by crosslinking the curable composition.
  • the present invention relates to a key compound-containing compound.
  • Fluorine-containing elastomers have excellent chemical resistance, solvent resistance, and heat resistance, and are therefore used in fields such as the automotive industry, semiconductor industry, and chemical industry as sealing materials in harsh environments. It is widely used.
  • composition containing a fluorine-containing elastomer in which a vinyl group, an aryl group or SiH is introduced at the terminal has been developed.
  • the fluorine-containing elastomer can be cross-linked because a vinyl group, a aryl group or a SiH group is present at the terminal.
  • this method is a method of crosslinking a fluorine-containing elastomer with an imidazole-based crosslinking agent, an oxazole-based crosslinking agent, or a thiazole-based crosslinking agent, and a molded product having excellent heat resistance can be obtained by crosslinking with these crosslinking agents.
  • the functional group is not introduced into one end of the fluorine-containing elastomer via the oxazole ring, imidazole ring or thiazole ring, the elastomer after the introduction of the oxazole ring, imidazole ring or thiazole ring is crosslinked. Can not do it. Disclosure of the invention
  • the present invention provides a method for producing a crosslinkable fluorine-containing elastomer containing specific functional groups at the main chain end and Z or side chain end, and a fluorine-containing elastomer obtained by the production method. Further, the present invention provides a curable composition that makes the best of the fluorine-containing elastomer, and a molded product obtained by crosslinking the curable composition. Furthermore, a silicon-containing compound is provided.
  • the present invention relates to a fluorine-containing elastomer (A) containing a functional group Z at the main chain end and Z or side chain end, a reactive group capable of cyclization with the functional group Z, and a functional group Y.
  • a crosslinkable fluorine-containing elastomer having a functional group Y at the main chain end and Z or side chain end which includes a step of performing a cyclization reaction with the organic compound (B) having a site that can be converted to the functional group Y. It relates to the manufacturing method.
  • the functional group Z is represented by the general formula (1):
  • X 1 is a chlorine atom, a fluorine atom, OH or OR 1
  • R 1 is an organic group having 1 to 10 carbon atoms which may contain an oxygen atom, a hydrogen atom, or a rogen atom.
  • the organic compound (B) has the general formula (2):
  • R 1 and R 2 are —NH, and the other is —NH 2, one NHR, —OH
  • R 4 is a monovalent organic group
  • Y 1 is a monovalent organic group having a functional group Y and a functional group ⁇ , or one having a site that can be converted to a functional group ⁇ . Is a valent group. It is preferable that
  • ⁇ 1 in the general formula (2) are alkenyl groups, Aruke - monovalent organic group having a group, a monovalent organic group having a hydrogen atom bonded to Keimoto atom or the general formula, (3 ):
  • R 5 , R 6 and R 7 are the same or different and each is a hydrogen atom or a monovalent hydrocarbon group which may contain a substituted or unsubstituted oxygen atom, and at least one of them. Is preferably a hydrogen atom or a monovalent organic group represented by a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group.
  • one of R and R is —NH, and the other is —NH, —NHR, —OH.
  • R 4 is a monovalent organic group
  • R 8 , R 9 , R 1 (> are the same force or different, each containing a hydrogen atom or a substituted or unsubstituted oxygen atom. May be monovalent charcoal It is a hydrogen fluoride group. )
  • the present invention also relates to a crosslinkable fluorine-containing elastomer having a functional group ⁇ at the main chain end and Z or side chain end, which is obtained by the production method.
  • the present invention provides the general formula (5) at the main chain terminal and the Z or side chain terminal:
  • X 2 is — 2—, —NR 11 —, —O—, —S—, R 11 is a monovalent organic group, and ⁇ 2 is an alkyl group, Or a monovalent organic group having an alkenyl group, a monovalent organic group having at least one hydrogen atom bonded to a silicon atom, or the general formula (3):
  • R 5 , R 6 and R 7 are the same or different and each is a hydrogen atom or a monovalent hydrocarbon group which may contain a substituted or unsubstituted oxygen atom, and at least one of them.
  • a crosslinkable fluorine-containing elastomer having a functional group Y represented by
  • the present invention relates to a curable composition having the fluorinated elastomer, and a molded product obtained by crosslinking the curable composition.
  • the present invention provides a fluorine-containing elastomer ( ⁇ ) containing a functional group ⁇ at the main chain end and ⁇ or side chain end, a functional group ⁇ or a site that can be converted into the functional group ⁇ , and the functional group ⁇ .
  • Production of a crosslinkable fluorine-containing elastomer having a functional group ⁇ at the main chain end and ⁇ or side chain end including a step of performing a cyclization reaction with an organic compound ( ⁇ ) having a reactive group capable of cyclization reaction It relates to the manufacturing method.
  • the fluorine-containing elastomer ( ⁇ ⁇ ) used in the present invention is not particularly limited as long as it is a fluorine-containing elastomer containing a functional group ⁇ at the main chain end and / or side chain end! Force It is preferable to have functional groups at both ends of the main chain from the viewpoint that it is possible to reduce terminal free chains that cause a reduction in the mechanical strength of the cured product after crosslinking.
  • an oxazole ring, a thiazole ring, and an imidazole ring can be formed by a cyclization reaction with a reactive group of the organic compound ( ⁇ ). ):
  • X 1 is a chlorine atom, a fluorine atom, OH or OR 1
  • R 1 is an organic group having 1 to 10 carbon atoms which may contain an oxygen atom or a halogen atom. is there.
  • organic group having 1 to C0 carbon atoms that may contain an oxygen atom or a halogen atom, preferably an alkyl group include CH, 1CH, 1CH, and the like.
  • the functional group Z is preferably COF because it has excellent reactivity with the organic compound (B) and can be easily introduced.
  • a monomer having the functional group Z or a site that can be converted into the functional group Z during the polymerization of the fluorine-containing elastomer (A) A method using a polymerization initiator having a functional group Z or a polymerization initiator having a moiety convertible to the functional group Z, or a terminal of a fluorine-containing elastomer having an iodine atom or a bromine atom at the terminal. The method of converting into the functional group Z is mentioned.
  • Examples of the fluorine-containing elastomer (A) include a fluorine rubber (a), a main chain ether-containing fluorine-containing polymer (b), and a rubber yarn composition having these forces.
  • fluororubber (a) examples include non-perfluorofluorororubber ( a1 ) and perfluorofluororubber ( a- 2).
  • the Pafuruorofutsu containing rubbers, Chi caries its constituent units refers to the 90 mole 0/0 or consisting par full O b monomer.
  • Examples of the main chain ether-containing fluorine-containing polymer include non-perfluoropolymer (b-1) and perfluoropolymer (b-2).
  • Non-perfluoro fluorine rubber ( a1 ) includes bi-lidene fluoride (VdF) fluorine rubber, tetrafluoroethylene (TFE) Z propylene fluorine rubber, tetrafluoroethylene (TFE).
  • VdF bi-lidene fluoride
  • TFE tetrafluoroethylene
  • TFE tetrafluoroethylene
  • VdF Z-propylene Z-vinylidene fluoride fluorine rubber, ethylene / hexafluoropropylene (HFP) fluorine rubber, ethylene Z-hexafluoropropylene (HFP) Z vinylidene fluoride (VdF) Fluororubber, ethylene Z hexafluoropropylene (HFP) / tetrafluoroethylene (TFE) fluororubber or fluorophosphazene fluororubber, etc., each of which can be used alone or without impairing the effects of the present invention. Any combination can be used within a range.
  • VdF fluororubber is preferably represented by the general formula (6).
  • M 1 One (M 2 ) — (N 1 ) One (6)
  • the structural unit M 1 is a structural unit derived from berylidene fluoride (m 1 )
  • the structural unit M 2 is a structural unit derived from a fluorine-containing ethylenic monomer (m 2 ).
  • N 1 is a repeating unit derived from the monomer (m 1 ) and the monomer (n 1 ) that can be copolymerized with the monomer (m 2 ).
  • the structural unit M 2 is 50 to 20 mol%.
  • the structural unit N 1 is preferably 0 to 10 mol% with respect to the total amount of the structural unit M 1 and the structural unit M 2 .
  • the fluorine-containing ethylenic monomer (m 2 ) one or two or more types of monomers can be used.
  • TFE tetrafluoroethylene
  • CFE black trifluoroethylene
  • HFP trifluoropropylene
  • tetrafluoropropylene tetrafluoropropylene
  • pentafluoropropylene trifluorobutene
  • tetrafluoroisobutene perfluoro (alkyl butyl ether)
  • PAVE perfluoro
  • tetrafluoroethylene, hexafluoropropylene, and perfluoro (alkyl butyl ether) are preferable.
  • the monomer (n 1 ) may be any monomer as long as it is copolymerizable with the monomer (m 1 ) and the monomer (m 2 ).
  • ethylene, propylene, alkyl For example, bull ether.
  • a monomer having a crosslinking site a monomer having a functional group Z, or a monomer giving a site that can be converted to the functional group Z is preferable.
  • CY 3 CY 3 -R 1 CHR 12 X 3 (7)
  • Y 3 represents a hydrogen atom, a fluorine atom or —CH 3 , a fluoroalkylene group
  • R 12 is a hydrogen atom or CH
  • X 3 is an iodine atom or bromine atom.
  • p is an integer of 1 to L0
  • examples thereof include perfluorocarbons as described in JP-B-5-63482 and JP-A-7-316234.
  • Iodine-containing monomers such as (6, 6-dihydro-1 6-oxo 1-hexene) and perfluoro (5 3 3-oxa 1 pentene)
  • CF CFOCF CF CH described in JP-A-4-217936
  • I-containing monomers such as I, described in JP-A-4 505341
  • Y 4 is a hydrogen atom or a fluorine atom, and n is an integer of 1 to 8)
  • n is an integer from 0 to 5)
  • CF CFCF (OCF (CF) CF)
  • n is an integer from 1 to 4.
  • n is an integer from 2 to 5
  • n is an integer from 1 to 6)
  • n is an integer from 1 to 2
  • n is an integer from 0 to 5
  • X 5 is a cyano group (one CN group), a carboxyl group (one COOH group) or an alkoxy carbo group (COOR 13 group, R 13 has 1 to 10 carbon atoms) And a monomer represented by an alkyl group). These can be used alone or in any combination.
  • VdF fluoride (VdF) fluororubber examples include VdF-H FP rubber, VdF—HFP—TFE rubber, VdF—CTFE rubber, VdF—CTFE—TFE. Preferred are rubbers.
  • TFE Z propylene-based fluororubber is preferably represented by the general formula (22).
  • the structural unit M 3 is a structural unit derived from tetrafluoroethylene (m 3 )
  • the structural unit M 4 is a structural unit derived from propylene (m 4 )
  • the structural unit N 2 is a single unit.
  • It is a repeating unit derived from monomer (n 2 ) copolymerizable with isomer (m 3 ) and monomer (m 4 ))
  • Tetrafluoroethylene (TFE) Z propylene-based fluororubber represented by the general formula (22)
  • TFE Tetrafluoroethylene
  • the structural unit M 4 to 60-30 mol%, including those of preferably 50 to 60 mol of structural units M 3 than good Mashigu 0/0
  • the structural unit M 4 are those containing from 50 to 40 mole 0/0.
  • the structural unit N 2 is preferably 0 to 40 mol% based on the total amount of the structural unit M 3 and the structural unit M 4 ! /.
  • any monomer can be used as long as it is copolymerizable with the monomer (m 3 ) and the monomer (m 4 ). It is preferable that For example, vinylidene fluoride, ethylene and the like.
  • structural unit M 5 is a structural unit derived from tetrafluoroethylene (m 5 )
  • structural unit M 6 is a structural unit derived from perfluoro (alkyl butyl ether) (m 6 ).
  • N 3 is a repeating unit derived from monomer (m 5 ) and monomer (n 3 ) copolymerizable with monomer (m 6 )
  • the structural unit M 5 5 0 to 90 mole 0/0 preferably those of the structural unit M 6 containing 10 to 50 mol% instrument more preferably structural units M 5 50 to 80 mole 0/0, which the structural unit M 6 comprising 20 to 50 mole 0/0, more preferably a structural unit M 5 55 to 70 mol%, the structural unit the M 6 are those containing 30 to 45 mol%.
  • perfluoro (alkyl butyl ether) examples include perfluoro (methyl butyl ether) and perfluoro (propyl butyl ether). These may be used alone or in any combination. Can do.
  • the monomer (n) may be any monomer as long as it is copolymerizable with the monomer (m 5 ) and the monomer (m 6 ). Or a monomer having a functional group Z or a monomer that provides a site that can be converted to the functional group Z.
  • Examples of the monomer that provides a site that can be converted to the group z include bi-lidene fluoride, an iodine or bromine-containing monomer represented by the general formula (7), and a single monomer represented by the general formula (8).
  • monomers represented by the general formula (9), such as those described in JP-B-5-63482 and JP-A-7-316234 !, such as perfluoro (6, 6 dihydro Iodine-containing monomers such as 6 chloro 3 oxa 1 hexene) and perfluoro (5 chloro 3 oxa 1 pentene), CF CFOCF CF described in JP-A-4217936
  • Iodine-containing monomers such as CH I, bromine described in JP-A-4-505341
  • Cyano group, carboxyl group, alkoxycarbol group force An oxazole ring, a thiazole ring, and an imidazole ring can be formed by a cyclization reaction with a reactive group possessed by the organic compound (B). Further, when the terminal is an iodine atom or a bromine atom, the fluorine-containing elastomer (A) used in the present invention can also be obtained by using an oxidation reaction or an addition reaction.
  • strong perfluorinated rubber examples include WO 97Z24381 pamphlet, JP-B 61-57324, JP-B 4-81608, JP-B 5-13961, etc. And fluororubber described in the above.
  • fluororubber ( a ) a fluorine-containing elastomer having a carboxyl group at the end of the main chain, which uses ammonium persulfate, potassium persulfate, hydrogen peroxide, or the like as a polymerization initiator is preferable.
  • fluorine-containing elastomer include fluorine-containing elastomers described in International Publication No. 03/076484 pamphlet and International Publication No. 00/29479 pamphlet.
  • the fluororubber (a) has fluidity at room temperature in that a molded product having a complicated shape can be easily obtained and on-site molding can be performed.
  • the above “normal temperature” means 0 to 50 ° C.
  • the fluororubber (a) having fluidity at room temperature preferably has a viscosity at room temperature of 0.1 to 2000 Pa's 1 to: LOOOPa's. More preferred. Viscosity If it is less than 0. lPa's, the polymer chain tends to be too short to be crosslinked, and if it exceeds 2000 Pa-s, it may not have fluidity at room temperature, resulting in a molded product with a complicated shape. Tend to be difficult.
  • the fluororubber (a) having fluidity at room temperature is preferably 50 to 75 having a mu-1 viscosity of 5 to 100 at room temperature. If the viscosity is less than 5, the polymer chain tends to be too short to be crosslinked, and if it exceeds 100, it may not have fluidity at room temperature. Tend to be difficult to obtain.
  • the Mu-one viscosity is a value obtained by measurement using a Mu-one viscometer MV2000 (manufactured by Monsantone) in accordance with JIS K 6300 (1994).
  • the radical polymerization initiator used for the polymerization may be the same as that conventionally used for the polymerization of the fluorine-containing elastomer.
  • These initiators include organic and inorganic peroxides and azo compounds.
  • Typical initiators include persulfates, peroxide carbonates, peroxyesters, and the like.
  • Preferred initiators include ammonium persulfate (APS). APS can be used alone or in combination with a reducing agent such as sulfite or sulfite.
  • a wide range of emulsifiers can be used as the emulsion polymerization. From the viewpoint of suppressing the chain transfer reaction to the emulsifier molecules during the polymerization, a fluorocarbon chain or a fluoropolyether chain is used. Desirable salts of carboxylic acids having The amount of emulsifier used is preferably about 0.05 to 2% by weight of the added water, and more preferably 0.2 to 1.5% by weight.
  • the monomer mixed gas used in the present invention is the same as that in G. H. Kalb et al., Advances in Chemistry Series., 129, 13 (197
  • the polymerization pressure can be varied within a wide range. Generally, it is in the range of 0.5-7 MPa. The higher the polymerization pressure, the higher the polymerization rate. From the viewpoint of improving productivity, It is preferably 8 MPa or more.
  • fluorine-containing non-perfluoropolymer (b-1) containing a main chain ether examples include polymers of 2,2,3,3-tetrafluorooxetane, and JP-A 64-85218. It is synthesized by the method described in the publication.
  • the main chain ether-containing fluorine-containing perfluoropolymer (b-2) includes hexafluoropropylene oxide polymer and 2,2,3,3-tetrafluorooxetane hydrogen. Converted to fluorine, non-fluorinated polyether hydrogen converted to fluorine, using a reaction between perfluoromonomer such as tetrafluoroethylene and oxygen, or reaction between fluorine-containing monomer and oxygen And polymers obtained by perfluorination by fluorination reaction.
  • Hexafluoropropylene oxide polymers can be synthesized by methods such as USP36603 15 and Makromol. Chem. 193, 2211-2219 (1992).
  • the A polymer of 2,2,3,3-tetrafluorooxetane in which hydrogen is converted to fluorine is synthesized by a method described in JP-A No. 64-85218.
  • a polymer obtained by reacting a fluorine-containing monomer with oxygen is synthesized by a method described in JP-A-61-187726 and JP-B-50-28409.
  • the fluorine-containing elastomer (A) used in the present invention contains a perfluoroalkylene unit and a Z or perfluoropolyether structure because it is excellent in heat resistance and chemical resistance and is easy to synthesize.
  • a polymer of hexafluoropropylene oxide and a copolymer of tetrafluoroethylene and perfluoroalkyl butyl ether are preferable.
  • the main chain ether-containing fluoropolymers are preferred because they are excellent in low-temperature properties, and the main chain ether-containing perfluoropolymers are preferred in terms of excellent low-temperature properties, heat resistance, and chemical resistance.
  • the number average molecular weight of the fluorine-containing elastomer (A) used in the present invention is preferably 800 to 500000, more preferably 3000 to 100000, more preferably than force S. If the molecular weight is less than 800, the hardness of the cured product tends to increase and it becomes difficult to form a three-dimensional network structure by crosslinking. There is a tendency, and when it exceeds 500,000, the viscosity tends to be high and the moldability tends to decrease.
  • the fluorine-containing elastomer (A) has a number average molecular weight of preferably 800 to 20000, more preferably 900 to 10,000. When the number average molecular weight is within this range, it is possible to obtain a molded article having fluidity at room temperature and a complicated shape.
  • the number average molecular weight is a value determined by size exclusion chromatography (HLC-8020 manufactured by Tosoh Corporation, polystyrene standard).
  • the organic compound (B) having a functional group Y or a site that can be converted to the functional group Y and a reactive group capable of undergoing a cyclization reaction with the functional group Z includes a fluorine-containing elastomer (A ) And a cyclization reaction are not particularly limited.
  • the reactive group is preferably a reactive group capable of forming an oxazole ring, thiazole ring, or imidazole ring by cyclization reaction with the functional group Z of the fluorine-containing elastomer (A). .
  • the organic compound (B) the oxazole ring, thiazole ring, and imidazole ring can be formed by cyclization reaction with the functional group Z, from the general formula (2):
  • R 2 and R 3 are —NH, and the other is —NH 2, one NHR 4 , —OH
  • R 4 is a monovalent organic group
  • Y 1 is a monovalent organic group having a functional group Y and a functional group ⁇ , or one having a site that can be converted to a functional group ⁇ . Is a valent group.
  • Upsilon 1 thing preferred tool formula (2) is found Aruke - group, a monovalent organic group having an alkenyl group, a monovalent organic group having a hydrogen atom bonded to Kei atom, Or general formula (3)
  • R 5 , R 6 , R 7 are the same force or different, each being a hydrogen atom or a monovalent hydrocarbon group that may contain a substituted or unsubstituted oxygen atom, and at least one of them. Is more preferably a monovalent organic group represented by a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group.
  • Y 1 is preferably a group represented by the general formula (3) from the viewpoint of excellent hydrosilylation reaction reactivity and excellent heat resistance at the crosslinking point.
  • R 2 and R 3 are a combination of —NH and OH. Yes, cheer
  • R 2 and R 3 are a combination of —NH and SH.
  • R 2 and R 3 are both —NH forces, or —NH and —
  • NHR 4 combinations can be selected.
  • the raw materials of the organic compound (B) can be obtained at low cost, so R 2 and R 3 are mixed with —NH and —OH.
  • Preferred to form a sazol ring Preferred to form a sazol ring.
  • R 4 is a monovalent organic group, and examples of the monovalent organic group include, but are not limited to, an aliphatic hydrocarbon group, a phenyl group, and a benzyl group. Specifically, for example, a lower alkyl group having 1 to 10 carbon atoms, particularly 1 to 6 carbon atoms such as —CH 2, 1 CH, 1 CH;
  • Fluorine atom-containing lower alkyl group phenyl group; benzyl group; C F, 1 CH C F, etc.
  • CF 1 to 5 hydrogens in CF such as H (CF), 1 CH C H (CF) (n is an integer from 1 to 5)
  • Examples thereof include a phenyl group or a benzyl group in which an atom is substituted.
  • a phenol group and —CH are preferred because they are particularly excellent in heat resistance, have good crosslinking reactivity, and are relatively easy to synthesize.
  • Examples of the alkyl group for Y 1 include a bur group, a allyl group, a probe group, an isopropyl group, a butyr group, an isobutenyl group, a hexyl group, a cyclohexyl group, and the like. Number of carbon atoms
  • alkenyl groups can be mentioned.
  • a monovalent having a alkenyl group of Y 1 examples include alkoxyalkyl groups such as a vinyloxycetyl group, an aryloxychetyl group, and a hexyloxypropyl group.
  • Examples of the monovalent organic group having a hydrogen atom bonded to the Y 1 key atom include dimethylhydrogensilyldimethylsilyl group and dimethylhydrogensilylethyldimethylsilyl group.
  • R 5 in the general formula (3) R 7 is a hydrogen atom or a monovalent hydrocarbon group which may contain a substituted or unsubstituted oxygen atom, and at least one of them is a hydrogen atom or alkenyl.
  • Examples of the unsubstituted monovalent hydrocarbon group include an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group, and an alkenyl group.
  • Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, and an octyl group.
  • Nonyl group, decyl group and the like having 1 to 3 carbon atoms LO alkyl group, and more representative examples are lower alkyl having 1 to 3 carbon atoms such as methyl group, ethyl group and propyl group.
  • Examples of the cycloalkyl group include cycloalkyl groups having 3 to 8 carbon atoms such as cyclopentyl, cyclohexyl, and cycloheptyl, and more representative examples include a cyclopentyl group and a cyclopentyl group.
  • a cycloalkyl group having 5 to 6 carbon atoms such as a hexyl group.
  • aryl group examples include aryl groups having 6 to 15 carbon atoms such as phenyl group, tolyl group, xylyl group, naphthyl group, biphenyl group, and the like.
  • aryl groups having 6 to 8 carbon atoms such as a phenol group, a tolyl group, and a xylyl group.
  • Examples of the aralkyl group include aralkyl groups having 7 to 7 carbon atoms such as a benzyl group, a phenyl group, a phenylpropyl group, and a methylbenzyl group, and more representative examples thereof. Is a aralkyl group having 7 to 8 carbon atoms, such as a benzyl group or a phenyl group.
  • Examples of the alkenyl group include carbons such as a vinyl group, a aryl group, a propenyl group, an isopropyl group, a butyl group, an isobutyl group, a hexyl group, and a cyclohexyl group. Examples thereof include alkenyl groups having 2 to 10 atoms, and more representative examples thereof are alkenyl groups having 2 to 4 carbon atoms such as vinyl group, allyl group and butyr group.
  • the substituted monovalent hydrocarbon group includes a (meth) atalylooxypropyl group, and! / ⁇ represents at least a part of the hydrogen atoms of the unsubstituted monovalent hydrocarbon group as a fluorine atom.
  • the group represented by the general formula (3) is relatively inexpensive, easy to synthesize, and excellent in cross-linking reactivity.
  • Y 1 is an alkenyl group, a monovalent organic group having an alkenyl group, or R 5 from the viewpoint of excellent stability of the crosslinking group.
  • Heat resistance of a molded article of a curable composition comprising a fluorine-containing elastomer preferably represented by the general formula (3) in which at least one of R 7 is a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group
  • R 7 is a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group
  • organic compound (B) specifically,
  • organic compound (B) since it is inexpensive and easy to synthesize, it contains a monovalent organic group having an alkenyl group, and the j8 position of the amino group and amino group.
  • An aliphatic hydrocarbon compound having a hydroxyl group, an amino group or a mercapto group bonded thereto is preferred. Specifically, because the raw materials are cheap and easy to synthesize,
  • Y 5 is a monovalent organic group having a alkenyl group or an alkenyl group, a monovalent organic group having a hydrogen atom bonded to a silicon atom, or a compound represented by the general formula (3):
  • R 5 , R 6 and R 7 are the same or different and each represents a hydrogen atom or a monovalent hydrocarbon group which may contain a substituted or unsubstituted oxygen atom, and at least one of them. Is a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group.
  • examples of Y in the formula include the same groups as Y 1 described above.
  • the addition amount of the organic compound (B) is preferably 1 to 5 moles relative to 1 mole of the functional group Z of the fluorine-containing elastomer (A). It is more preferable. If the addition amount is less than 0.5 mol, there is a tendency that a sufficient crosslinking group cannot be introduced into the fluorine-containing elastomer. Yes.
  • the cyclization reaction conditions are not particularly limited as long as they are appropriately selected depending on the types of the fluorine-containing elastomer (A) and the organic compound (B).
  • a solvent may be used to increase the reaction rate of the cyclization reaction.
  • the solvent it is preferable to use either a fluorine-containing elastomer (A) or an organic compound (B) or a solvent in which both are soluble, and a solvent in which both are soluble is more preferable.
  • the solvent to be used is appropriately selected according to the structures of the fluorine-containing elastomer (A) and the organic compound (B), but the functional group Z of the fluorine-containing elastomer (A) and the organic compound (B) Preferred is a solvent that is not reactive with the amino group, hydroxyl group or mercapto group.
  • the reaction is preferably performed at 50 to 250 ° C for 0.1 to 15 hours.
  • examples of the cyclization reaction include the following reactions.
  • Examples of the functional group ⁇ of the crosslinkable fluorine-containing elastomer of the present invention obtained by the cyclization reaction include ⁇ 1 of the organic compound ( ⁇ ), and are alkenyl groups because they can be cured by a hydrosilylation reaction. Or a monovalent organic group having an alkyl group, a monovalent organic group having at least one hydrogen atom bonded to a silicon atom, or the general formula (3):
  • R 5 , R 6 , and R 7 are the same or different and each represents a hydrogen atom or a monovalent hydrocarbon group that may contain a substituted or unsubstituted oxygen atom, and at least one of them. Is preferably a hydrogen atom or a monovalent organic group represented by a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group.
  • the organic compound (B) a compound having a site that can be converted to the functional group Y is preferable.
  • the site that can be converted to the functional group Y iodine or bromine, which is preferably halogen, is particularly preferable because it can be converted by a Grignard reaction or a coupling reaction.
  • X 2 is - NH -, - NR 11 -, - O -, - a S-
  • R 11 is a monovalent organic group
  • Y 2 is, Aruke - group, Or a monovalent organic group having an alkenyl group, a monovalent organic group having at least one hydrogen atom bonded to a silicon atom, or the general formula (3):
  • R 5 , R 6 and R 7 are the same force or different, each being a hydrogen atom or a monovalent hydrocarbon group which may contain a substituted or unsubstituted oxygen atom, and at least one of them. Is a monovalent organic group represented by a hydrogen atom or a substituted or unsubstituted monovalent hydrocarbon group having an alkenyl group. )
  • the monovalent organic group of R 11 is not particularly limited as long as it is the monovalent organic group described above.
  • an unsaturated group or a -SiH group can be introduced into the main chain terminal and Z or side chain terminal of the fluorine-containing elastomer via a specific ring structure.
  • a specific ring structure it is excellent in heat resistance and chemical resistance, and by cross-linking such a curable composition comprising a fluorine-containing elastomer, a molded product having excellent heat resistance and chemical resistance can be obtained. It can be obtained.
  • the curable composition of the present invention will be described.
  • the curable composition of the present invention comprises a crosslinkable fluorine-containing elastomer having a functional group Y at the main chain end and Z or side chain end.
  • the inclusion of a compound is preferable from the viewpoint of obtaining a sufficiently crosslinked cured product.
  • Preferred examples of the compound capable of crosslinking reaction include polyfunctional compounds having a plurality of functional groups capable of reacting with the fluorine-containing elastomer in the molecule.
  • the polyfunctional compound it is preferable to use a polyfunctional compound having at least 2 functional groups per molecule and, if necessary, 3 or more, from the viewpoint of sufficient crosslinking.
  • polyfunctional compound corresponding to the cross-linked site of the fluorine-containing elastomer.
  • the power to give a specific example of the polyfunctional compound The polyfunctional compound may be used alone or in combination of two or more.
  • the crosslinkable site is an alkenyl group
  • preferred examples of the polyfunctional compound include a compound having a SiH group and a polyfunctional unsaturated compound.
  • the compound containing a SiH group acts as a crosslinking agent for the fluorine-containing elastomer.
  • the SiH group-containing compound is not particularly limited as long as it has two or more hydrogen atoms bonded to a silicon atom, that is, a hydrosilyl group (SiH group) in one molecule, but the fluorine-containing elastomer is not limited.
  • a hydrosilyl group SiH group
  • the fluorine-containing elastomer is not limited.
  • one or more monovalent perfluoroalkyl groups, monovalent perfluoroalkyl groups, divalent perfluoro groups in one molecule Those having a fluoroalkylene group or a divalent perfluoroalkylene group are preferred.
  • Examples of the perfluorooxyalkyl group, the perfluoroalkyl group, the perfluoroalkylene group, and the perfluoroalkylene group include those represented by the following general formula.
  • n is an integer of 1 to 5
  • Divalent linking groups that connect these perfluoroalkyl groups, perfluoroalkylalkyl groups, perfluoroalkylene groups, or perfluoroalkylene groups with the silicon atoms include alkylene groups, arylenes, and the like. Specifically, a group or a combination thereof, or an ether bond oxygen atom, an amide bond, a carbonyl bond, or the like may be interposed between these groups, —CH 2 CH 1, —CH 2 CH 2 CH 2 — , — CH CH CH ⁇
  • Ph is a phenol group
  • Examples thereof include those having 2 to 12 carbon atoms such as O—CO—.
  • the monovalent or divalent fluorine-containing substituent in the compound containing a SiH group that is, a perfluoroalkyl group, a perfluoroalkylalkyl group, a perfluoroalkylene group, or a perfluorooxy group.
  • Examples of the monovalent substituent bonded to the silicon atom include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, a cyclohexyl group, an octyl group, and a decyl group; An alkenyl group such as a aryl group; an aryl group such as a phenyl group, a tolyl group and a naphthyl group; an aralkyl group such as a benzyl group and a ferroethyl group; and at least some of the hydrogen atoms of these groups are chlorine atoms; Examples thereof include unsubstituted or substituted hydrocarbon groups having 1 to 20 carbon atoms, such as chloromethyl group, chloropropyl group, and cyanoethyl group, which are substituted with a cyano group.
  • the compound having a SiH group a compound having a structure that is difficult to be decomposed under acidic or alkaline conditions is used in order to improve chemical resistance such as acid resistance and alkali resistance of the cured product. Also preferred.
  • a compound having a structure that is difficult to be decomposed under acidic or alkaline conditions a compound that does not have a Si-O Si bond is preferred, and a compound described in JP-A-2001-354764, or Examples thereof include compounds described in 2002-12597.
  • the compound containing a SiH group may be any of cyclic, chain, three-dimensional network, and combinations thereof.
  • the number of key atoms of the organic key compound is not particularly limited, but is usually about 2 to 60, preferably about 3 to 30.
  • Examples of such organic cage compounds include the following compounds.
  • Me represents a methyl group
  • Ph represents a phenyl group. These compounds can be used alone or in combination of two or more.
  • n is an integer of 1 to 30
  • m is an integer of 1 to 30
  • n + m is 2 to 60, average 2 to
  • n is an integer of 1 to 30
  • m is an integer of 1 to 30
  • n + m is 2 to 60, average 2 to
  • n represents an integer of 2 to 60 and an average of 3 to 50
  • n represents an integer of 2 to 60 and an average of 3 to 50.
  • n represents an integer of 2 to 60 and an average of 3 to 50
  • the crosslinking site has a fluorine-containing elastomer which is a monovalent organic group having at least one unsaturated bond, such as a monovalent organic group having at least one alkenyl group or alkenyl group, and the SiH group.
  • a fluorine-containing elastomer which is a monovalent organic group having at least one unsaturated bond, such as a monovalent organic group having at least one alkenyl group or alkenyl group, and the SiH group.
  • a hydrosilylation reaction catalyst from the viewpoint of the reactivity of the hydrosilylation reaction.
  • the hydrosilylation reaction catalyst may be any catalyst that promotes the addition reaction (fluorene hydrosilylation reaction) between a fluorine-containing elastomer and a compound having two or more Si H groups in one molecule.
  • an addition reaction catalyst comprising a platinum group element such as a platinum-based catalyst, a palladium-based catalyst, or a rhodium-based catalyst (Group 8 metal catalyst such as Group 8 metal, Group 8 metal complex, Group 8 metal compound, etc.
  • platinum-based catalysts are preferred because they are relatively easily available.
  • the platinum-based catalyst is usually a known one used for addition-curing type curing.
  • platinum alone platinum black
  • chloroplatinic acid complex of chloroplatinic acid and olefins such as ethylene
  • salt ⁇ complex of platinic acid and alcohol or bursiloxane silica, alumina, carbon, etc.
  • Platinum supported on the carrier platinum alone (platinum black); chloroplatinic acid; complex of chloroplatinic acid and olefins such as ethylene; salt ⁇ complex of platinic acid and alcohol or bursiloxane; silica, alumina, carbon, etc. Platinum supported on the carrier.
  • the palladium-based catalyst is composed of palladium, a palladium compound, chloropalladic acid
  • the rhodium-based catalyst is composed of rhodium, a rhodium compound, salted rhodium acid, and the like.
  • RhCl (PPh) RhCl (CO) (PPh)
  • RhCl (CH) RhCl (CH)
  • the hydrosilylation reaction catalyst may also be a Lewis acid, cobalt carbo- hydrate, and the like.
  • reaction inhibitors include benzotriazole; acrylonitrile; N, N diallylacetoamide, N, N diallyl benzamide, N, N,, ', ⁇ , -tetraaryl- ⁇ phthalic acid diamide, ⁇ , ⁇ , ⁇ ', ⁇ , -Tetralylulu m-phthalic acid diamide, N, N, ⁇ ', ⁇ , -tetraaryl- ⁇ -phthalic acid diamide, etc .; ai; phosphorus; nitrogen; aminic compound; Phosphorus compound; Tin; Tin compound; Tetramethyltetravinylcyclotetrasiloxane; Hyde mouth peroxide and other organic peroxides.
  • reaction inhibitor examples include, for example, 1-Lu 1-hydroxycyclohexane, 2-methyl-3-butyne-2ol, 3,5 dimethyl-1, monohex-3-ol, and phenol.
  • -Acetylene alcohols such as rubutinol, 3-methyl-3-pentene 1-yne, 3,5 dimethyl 1-3 hexene 1-yne, 3-methyl 1-pentene 1-3-ol, US Pat. No. 3,445,420 It may be a compound exemplified as the compound (4) in the specification, or a acetylene compound such as a compound exemplified as the component (2) in JP-B-54-3774.
  • the crosslinkable site has a structure having a -SiH group
  • the addition amount of the crosslinkable fluorine-containing elastomer of the present invention and the compound capable of crosslinking reaction is such that the fluorine-containing compound of the crosslinkable compound is capable of crosslinking with respect to 1 mol of the functional group Y of the crosslinkable fluorine-containing elastomer.
  • the reactive group capable of reacting with the elastomer is preferably 0.2 to 20 mol, and more preferably 0.5 to 10 mol. If the amount is less than 2 mol, there is a tendency that sufficient crosslinking cannot be performed, and if the amount exceeds 20 mol, crosslinking cannot be performed sufficiently.
  • the curable composition of the present invention can be expected to have a function as a processing aid, and therefore other fluorinated elastomers that are not included in the fluorinated elastomer obtained by the production method of the present invention described above. Including, ok.
  • the curable composition of the present invention includes a reduction in thermal shrinkage at the time of curing, a decrease in the thermal expansion coefficient of the elastic body obtained by curing, thermal stability, weather resistance, chemical resistance, flame retardancy, or A filler may be added for the purpose of improving the mechanical strength and lowering the gas permeability.
  • the additive include silica such as fumed silica and precipitated silica, quartz powder, glass fiber, carbon, iron oxide, titanium oxide, cerium oxide and other metal oxides, calcium carbonate, magnesium carbonate, and the like.
  • the metal carbonate can be mentioned.
  • an appropriate pigment, dye or anti-oxidation agent can be added.
  • the curable composition of the present invention can be prepared by adding usual additives, for example, processing aids, plasticizers, colorants, acids, and the like, which are blended into the curable composition that is fluorinated elastomer as necessary.
  • processing aids for example, processing aids, plasticizers, colorants, acids, and the like
  • ⁇ ⁇ ⁇ Anti-aging agents, anti-aging agents, ozone degrading agents, UV absorbers, etc. can be added, and one or more conventional cross-linking agents and cross-linking aids different from the above may be added.
  • Each component can be prepared by mixing using an ordinary elastomer processing machine such as an open roll, a Banbury mixer, a kneader or the like.
  • the curable composition thus obtained is crosslinked and molded according to a conventional method. That is, it is molded by compression molding, injection molding, extrusion molding, calender molding, dip molding, coating, etc. by dissolving in a solvent.
  • the crosslinking conditions vary depending on the molding method and the shape of the molded product, but are generally in the range of 100 ° C to 300 ° C for several seconds to 5 hours. In order to stabilize the physical properties of the cross-linked product, You may go on a bridge. Secondary crosslinking conditions are 150 ° C to 300 ° C for 30 minutes to 48 hours.
  • the fluorine-containing elastomer obtained by the production method of the present invention has a low molecular weight and is fluid at normal temperature, it can be mixed with a planetary mixer or a tabletop mixer. At this time, the temperature may be increased to 50 ° C or higher in order to increase the mixing efficiency.
  • a curable composition having fluidity at room temperature is usually processed with an extrusion gun such as hot melt gun at a temperature of 200 ° C or lower, injection molding or extrusion molding with a LIMS (Liquid Injection Molding System) molding machine, Molding can be performed by pouring into a mold at room temperature to 200 ° C.
  • an extrusion gun such as hot melt gun at a temperature of 200 ° C or lower
  • LIMS Liquid Injection Molding System
  • the molded article of the present invention can be suitably used in the following fields.
  • semiconductor-related fields such as semiconductor manufacturing equipment, liquid crystal panel manufacturing equipment, plasma panel manufacturing equipment, plasma addressed liquid crystal panels, field emission display panels, solar cell substrates, o (square) rings, packings, sealing materials, tubes Rolls, coatings, linings, gaskets, diaphragms, hoses, adhesives, etc.
  • semiconductor manufacturing equipment liquid crystal panel manufacturing equipment, plasma panel manufacturing equipment, plasma addressed liquid crystal panels, field emission display panels, solar cell substrates, o (square) rings, packings, sealing materials, tubes Rolls, coatings, linings, gaskets, diaphragms, hoses, adhesives, etc.
  • CVD equipment dry etching equipment, wet etching equipment, oxidation diffusion equipment, sputtering equipment, ashing equipment, cleaning equipment, ion implantation. It can be used for equipment, exhaust equipment, chemical piping, and gas piping.
  • the gate valve O-ring and seal material the quartz window O-ring and seal material, the chamber O-ring and seal material as the gate O-ring and seal material as the bell jar O-ring and seal O-ring of coupling as seal material, O-ring of pump as seal material, seal material, diaphragm, O-ring of gas control device for semiconductor, O-ring for seal developer as seal material, seal material Wafer for wafer cleaning solution, tube as a wafer material, roll for wafer transfer, resist developer tank, stripping liquid tank lining, coating as wafer cleaning liquid tank lining, coating as plasma etching process, As an insulating layer for electrostatic chuck in ion implantation process, or wet etching Grayed tank lining, can be used as Kotin grayed.
  • sealing material 'sealing agent, optical fiber's quartz coating Covering materials, insulation, anti-vibration, waterproofing, moisture-proof electronic parts, circuit board potting, coating, adhesive seals, gaskets for magnetic storage devices, modified materials for sealing materials such as epoxies, clean room 'clean equipment Used as sealant.
  • gaskets, shaft seals, valve stem seals, sealing materials, coatings, pottings, protective agents, adhesives and hoses can be used for engines and peripheral devices, and hoses and sheathing materials are used for AT equipment.
  • hoses and sheathing materials are used for AT equipment.
  • 0 (square) rings, tubes, knocks, valve cores, hoses, seals and diaphragms can be used in fuel systems and peripheral devices.
  • rolls are listed, which are respectively used for a film developing machine, a tangential film developing machine, a printing roll, and a coating roll. be able to.
  • a developing roll of a film developing machine / coiled film image forming machine a gravure roll of a printing roll, a guide roll, a gravure roll of a magnetic tape manufacturing coating line of a coating tool, and a magnetic tape manufacturing coating It can be used as a line guide roll, various coating rolls, and the like.
  • dry copying machine seals printing equipment printing rolls, scrapers, tubes, valve parts, coating, coating equipment coating rolls, scrapers, tubes, valve parts, printer ink tubes, rolls, belts, dry copying machine belts It can be used as a roll, a roll for a printing press, a belt, or the like.
  • Tubes can also be used in the analysis and science machine field.
  • linings, valves, knockers, rolls, hoses, diaphragms, ⁇ (square) rings, tubes, sealing materials, belts, adhesives, etc. can be used for food manufacturing processes. it can. Specifically, it can be used as a plate-type heat exchanger seal, a solenoid valve seal of a vending machine, or the like.
  • hydraulic seals Specifically, hydraulic seals, lubrication machinery seals, bearing seals, dry cleaning equipment windows, other seals, uranium hexafluoride concentrator seals, cyclotron seal (vacuum) valves, automatic packaging machines It is used for seals, sulfurous acid gas in the air, diaphragms for chlorine gas analysis pumps (pollution measuring devices), printing press rolls, belts, pickling squeeze rolls, and so on.
  • a sealing material between electrodes and separators is used as a seal for hydrogen 'oxygen' production water piping.
  • the curable composition of the present invention makes use of the cleanliness, and is used for gaskets for magnetic recording devices (hard disk drives), semiconductor manufacturing equipment, and wafer storage devices such as wafer storage. It is particularly preferably used as a sealing material for clean equipment such as a sealing material.
  • the curable composition of the present invention utilizes characteristics such as chemical resistance, low gas permeability, and flame retardancy, and is used for fuel cells such as packing used between fuel cell electrodes and pipes around them. It is also particularly suitable for seal materials.
  • the present invention provides a compound of the general formula (4)
  • R 1 and R 2 are —NH, and the other is —NH 2, 1 NHR ′, —OH
  • R 4 is a monovalent organic group
  • R 8 , R 9 , R 1 (> are the same force or different, each containing a hydrogen atom or a substituted or unsubstituted oxygen atom. It may be a monovalent hydrocarbon group).
  • the silicon-containing compound of the present invention is exemplified by the same compounds as described above as —SiR 8 R 9 R 1Q in the general formula (4).
  • the fluorine-containing elastomer produced using this compound can be crosslinked by a hydrosilylation reaction.
  • the silicon-containing compound of the present invention is synthesized, for example, by the following method.
  • R ′′ and R 15 are groups obtained by converting the hydrogen atoms of R 2 and R 3 into protecting groups for the Grignard reaction.
  • any commonly used protecting group may be used.
  • n are each independently an integer of 1 to 25, and the average value of m + n is 30.
  • n are each independently an integer of 1 to 25, and the average value of m + n is 30.
  • n are each independently an integer of 1 to 25, and the average value of ⁇ ⁇ + 11 is 30.
  • a fluorine-containing elastomer (IX) having a composition of tetrafluoroethylene and perfluoromethylvinyl ether mixed in force was obtained.
  • the compound was confirmed by —NMR, 19 F-NMR, IR analysis.
  • Example 2 Instead of the compound ( ⁇ ) obtained in Example 1, the compound (VI) obtained in Example 2 was used. The synthesis was performed in the same manner as in Example 5 except that.
  • a fluorine-containing elastomer (X) having tetrafluoroethylene and perfluoromethyl vinyl ether having the above-mentioned composition was obtained.
  • the compound was confirmed by ⁇ -NMR, 19 F-NMR and IR analysis.
  • the fluorine-containing elastomer obtained in Example 3 (number average molecular weight 5390, vinyl group amount 0.03 7 mol / 100 g) 100 parts of fumed silica having a specific surface area of 300 m 2 / g treated with hexamethyldisilazane After adding 20 parts and heat-mixing, they were mixed on a three-roll mill. Furthermore, 0.3 parts of 50% toluene solution of ethurcyclohexanol and toluene solution of chloroplatinic acid bisiloxane complex (platinum concentration) 0.5 parts by weight) 0.2 parts, following formula (i):
  • a composition was prepared in the same manner except that 10.9 parts of the fluorine-containing organosilicon compound represented by [0261] was added, and the physical properties and chemical resistance of the cured product obtained under the same conditions were examined. The results are shown in Tables 1 and 2.
  • Example 7 Except for using 100 parts of the fluorine-containing polymer obtained in Example 4 (number average molecular weight 5390, bute group weight 0.037 mol ZlOOg) instead of the fluorine-containing elastomer obtained in Example 3 of Example 7. Prepared a composition in the same manner as in Example 7, and examined the physical properties and chemical resistance of the cured product obtained under the same conditions. The results are shown in Tables 1 and 2.
  • a composition was prepared in the same manner except that 10.9 parts of a fluorine-containing organosilicon compound of the following formula (ii) was added instead of the fluorine-containing hydrogen siloxane of the formula (i) of Example 9.
  • the cured product was examined for physical properties and chemical resistance. The results are shown in Tables 1 and 2.
  • Example 7 Except for using 142 parts of the fluorine-containing polymer obtained in Example 5 (number average molecular weight 7820, butyl group weight 0.026 mol ZlOOg) instead of the fluorine-containing elastomer obtained in Example 3 of Example 7. Prepared a composition in the same manner as in Example 7, and examined the physical properties and chemical resistance of the cured product obtained under the same conditions. The results are shown in Tables 1 and 2.
  • a specific functional group is introduced into the main chain terminal and specific sites at the end of the main chain or the side chain, particularly at the main chain terminal, by a cyclization reaction. It is possible to obtain a functional fluorine-containing elastomer. Further, by cross-linking the curable composition comprising the fluorine-containing elastomer, a molded product having excellent heat resistance and chemical resistance can be obtained.

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Abstract

La présente invention concerne un procédé de production d'un élastomère fluoré qui possède un résidu contenant un groupe fonctionnel au niveau de la terminaison du squelette et/ou de la terminaison d'une chaîne latérale ; un élastomère fluoré produit selon le procédé ; une composition durcissable comprenant l'élastomère fluoré ; un article moulé produit par la réticulation de la composition durcissable ; et un composé contenant du silicium. La présente invention concerne un procédé de production d'un élastomère fluoré réticulable possédant un groupe fonctionnel (Y) au niveau de la terminaison du squelette et/ou de la terminaison d'une chaîne latérale, le procédé comprenant l'étape consistant à réaliser la cyclisation entre (A) un élastomère fluoré possédant un groupe fonctionnel (Z) au niveau de la terminaison du squelette et/ou de la terminaison d'une chaîne latérale et (B) un composé organique possédant un groupe fonctionnel (Y) ou un segment capable d'être converti en un groupe fonctionnel (Y) et un groupe réactif capable d'être cyclisé avec le groupe fonctionnel (Z).
PCT/JP2006/317978 2005-09-16 2006-09-11 Élastomère fluoré, procédé de production d'élastomère fluoré et composé contenant du silicium Ceased WO2007032310A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03197436A (ja) * 1989-04-20 1991-08-28 Ausimont Srl 官能性フルオロポリエーテル
JPH05320329A (ja) * 1990-03-06 1993-12-03 Ausimont Spa 新規なペルフルオロポリエーテルおよびその製造法
JPH08198926A (ja) * 1995-01-23 1996-08-06 Shin Etsu Chem Co Ltd 含フッ素アミド化合物
JP2002322362A (ja) * 2001-02-20 2002-11-08 Shin Etsu Chem Co Ltd 含フッ素硬化性組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03197436A (ja) * 1989-04-20 1991-08-28 Ausimont Srl 官能性フルオロポリエーテル
JPH05320329A (ja) * 1990-03-06 1993-12-03 Ausimont Spa 新規なペルフルオロポリエーテルおよびその製造法
JPH08198926A (ja) * 1995-01-23 1996-08-06 Shin Etsu Chem Co Ltd 含フッ素アミド化合物
JP2002322362A (ja) * 2001-02-20 2002-11-08 Shin Etsu Chem Co Ltd 含フッ素硬化性組成物

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