Crosslinkable fluororubber composition and crosslinked rubber article

FIELD: chemistry.

SUBSTANCE: invention relates to a crosslinkable fluororubber composition which can yield a crosslinked rubber article, e.g., sealing material. A composition containing fluororubber and a compound of formula: (X-)x(Z-)zY, is crosslinked to form a crosslinked rubber article. In said formula, X denotes: U-(CF2)aO(CF2CF2O)b-, Z denotes: RFO(CF2CF2O)c-, Y denotes a (x+z) valent perfluoro saturated hydrocarbon group or a group having an ether oxygen atom embedded between carbon atoms thereof, x is an integer of at least 3, z is an integer of at least 0 and x+z is an integer of at least 3, U denotes a monovalent group having at least one element selected from a group consisting of an unsaturated hydrocarbon, a bromine atom and an iodine atom, RF denotes a C1-20 linear perfluoroalkyl group or a group having an ether oxygen atom embedded between carbon atoms thereof, a is an integer from 0 to 20, b is an integer from 1 to 200 and c is an integer from 3 to 200.

EFFECT: crosslinked rubber article has excellent flexibility at low temperature.

10 cl, 1 tbl, 6 ex

 

The technical field

The present invention relates to stapling a fluorine-containing elastomer composition, which can give a crosslinked rubber product excellent in flexibility at low temperature, and obtained from him a crosslinked rubber product.

The level of technology

As cross-linking processing fluoro known method of peroxide crosslinking of the silicone elastomer by mixing with an organic peroxide and heating the mixture, or a method of radiation crosslinking of the silicone elastomer by irradiation of radioactive rays, as described in the following patent document 1. At this point, in order to improve the properties of the crosslinking of the silicone elastomer or properties of the obtained crosslinked rubber products, pre-mixed with a polyfunctional compound as a co-crosslinking agent.

As of this polyfunctional compounds are preferably used, triallylisocyanurate (see non-patent document 1 and patent document 1). Using triallylisocyanurate as joint cross-linking agent, it is possible to improve the amount of crosslinking of the silicone elastomer. In addition, the triazine ring structure, excellent in heat resistance, is injected in place of stitching fluoro, and this is advantageous, as it can be obtained crosslinked rubber product excellent in heat resistance or mechanical properties.

Doc is ment prior art

Non-patent document

Non-patent document 1: Handbook of Fluororesins, pages 161 to 622 and 577 to 578, edited by Satokawa (published in 1990 by THE NIKKAN KOGYO SHIMBUN, LND.)

Patent document

Patent document 1: JP-a-7-179705

Description of the invention

Technical problem

However, silicone elastomer, especially a silicone elastomer having a tetrafluoroethylene as a copolymer component is poor in flexibility at low temperature and, thus, has a problem in the sealing property at low temperature environment.

Accordingly, the present invention is to provide a stapling fluorine-containing elastomer composition, which can give a crosslinked rubber product excellent in flexibility at low temperature, and the crosslinked rubber product.

Solution

The present invention provides the following:

[1] Stitched fluorine-containing elastomer composition comprising a silicone elastomer and a compound expressed by the following formula (A):

(X)x(Z)zY (A)

where X represents a group expressed by the following formula (X), Z represents a group expressed by the following formula (Z), Y denotes (x+z) valent perforacion hydrocarbon group or such a group having an etheric oxygen atom, embedded between its carbon atoms, x is an integer of at least 3, z is an integer,at measures 0, and x+z is an integer of at least 3

U-(CF2)andOn(CF2CF2O)b- (X)

RFO(CF2CF2O)with- (Z)

where U denotes a monovalent group having at least one element selected from the group consisting of unsaturated hydrocarbon, bromine atom and iodine atom, RFstands With1-20linear performanceline group or such a group having an etheric oxygen atom, embedded between its carbon atoms, and a is an integer from 0 to 20, b is an integer from 1 to 200, and C is an integer from 3 to 200.

[2] Stitched fluorine-containing elastomer composition according to p.[1], where the compound expressed by the formula (A) is a compound expressed by the following formula (A1):

(X)x1Y (A1)

where x1 is the number 3 or 4.

[3] Stitched fluorine-containing elastomer composition according to p.[3], where x1 in the formula (A1) is 3, and Y represents any of the groups (Y3-1) - (Y3-4) expressed by the following formulas:

[4] Stitched fluorine-containing elastomer composition according to p.[1], where the compound expressed by the formula (A) is a compound expressed by the following formula (A2):

where each of b1, b2 and b3, which are independent of each other, is an integer from 1 to 20.

[5] Stitched fluorine-containing elastomer composition according to any one of paragraphs[1]-[4], where the compound expressed by the formula (A), has srednekamennogo molecular weight (Mn) from 500 to 100000.

[6] Stitched fluorine-containing elastomer composition according to any one of paragraphs.[1]-[5], where the compound expressed by the formula (A) has a ratio (Mw/Mn) weighted average molecular weight Mw to srednekamennogo molecular weight Mn of 1.0 to 2.0.

[7] Stitched fluorine-containing elastomer composition according to any one of paragraphs.[1]-[6], which contains a compound expressed by the formula (A), in an amount of from 1 to 50 mass parts per 100 mass parts of the silicone elastomer.

[8] Stitched fluorine-containing elastomer composition according to any one of paragraphs.[1]-[7], where the silicone elastomer is at least one element selected from the group consisting of a copolymer of tetrafluoroethylene/propylene copolymer vinylidenefluoride/tetrafluoroethylene/hexaferrite and a copolymer of tetrafluoroethylene/perfluoroalkyl vinyl ether.

[9] Stitched fluorine-containing elastomer composition according to any one of paragraphs.[1]-[8], which further comprises an organic peroxide.

[10] Crosslinked rubber product formed by stitching the stitching fluorine-containing elastomer composition according to any one of paragraphs.[1]-[9].

[11] Crosslinked rubber article by p.[10], which is a sealing material.

The predominant effects of the invention

Stitched fluorine-containing elastomer composition of the present invention containing the compound expressed the n in the formula (a) above, has a wonderful stevenot, such as peroxy stevenote or radiation stevenot, and high magnitude stitching. In addition, the crosslinked rubber product of the present invention, formed by stitching this stitched fluorine-containing elastomer composition, has excellent flexibility at low temperature and good low-temperature characteristics, and has an excellent basic properties such as strength, hardness, modulus and permanent deformation under compression.

Description of embodiments

Hereinafter in this description, the compound expressed by the formula (a), is also known as compound (A). The same applies to other compounds. In addition, the group expressed by the formula (X), is called a group (X). The same applies to other groups.

(Changeable) a fluorine-containing elastomer composition)

Stitched fluorine-containing elastomer composition of the present invention has a composition containing at least a silicone elastomer and the following compound (A):

(X)x(Z)zY (A)

[Connect ()]

Now will be described compound (A) used in the stitching fluorine-containing elastomer composition of the present invention. The compound (A) operates as a joint cross-linking agent in the stitching fluorine-containing elastomer composition of the present invention.

X in the compound (A) is a monovalent group, irgendwo the following formula (X):

U-(CF2)andOn(CF2CF2O)b- (X)

In the group (X) and an integer from 0 to 20, preferably an integer from 0 to 10, particularly preferably an integer from 0 to 2. In addition, b is an integer from 1 to 200, preferably an integer from 1 to 100, particularly preferably an integer from 1 to 20. In addition, U is a monovalent group having at least one element selected from the group consisting of unsaturated hydrocarbon, bromine atom and iodine atom. As specific examples, when U represents a group having an unsaturated hydrocarbon, may be listed the following structures from (U-1) to (U-13).

Among them (U-8), (U-9), U-11 or U-12) is preferred because it has a structure having an allyl group associated with N, and U-11 or U-12) is particularly preferred.

In addition, as specific examples, when U represents a monovalent group, having a bromine atom, can be mentioned the following structures. In these formulas, n is an integer from 1 to 3.

Br(CH2)n-

Br(CH2)nC(O)O-CH2-

In addition, as specific examples, when U represents a monovalent group having an iodine atom, can be mentioned the following structures. In these formulas n RA is but an integer from 1 to 3.

I(CH2)n-

I(CH2)nC(O)O-CH2-

As a group (X) structure expressed by the following formula (X1), is preferred.

U-CF2O(CF2CF2O)b- (X1)

In the compound (A) Z represents a monovalent group expressed by the formula (Z):

RFO(CF2CF2O)with- (Z)

In the group (Z) with integer from 3 to 200, preferably an integer from 3 to 100, particularly preferably an integer from 5 to 50. In addition, RFrepresents a C1-20linear performanceline group or such a group having an etheric oxygen atom, embedded between its carbon atoms, and is particularly preferably has 1 to 16 carbon atoms. As specific examples of RFcan be mentioned the following groups. In these formulas, s is an integer from 0 to 15, CyFrepresents perftorirovannogo group, t is an integer from 0 to 15, AdFrepresents perftordecaline group, and t is an integer from 0 to 15.

CF3(CF2)s-

CyF-(CF2)t-

AdF-(CF2)t-

In the compound (A) Y means (x+z) valent perforacion hydrocarbon group or such a group having an etheric oxygen atom is introduced between the atoms of carbon is and. x+z as the valency of the group (Y) is an integer of at least 3, preferably from 3 to 110, particularly preferably from 3 to 9.

As specific examples of the group (Y) is a trivalent group, can be specified (Y3-1)-(Y3-4) group, where the group (Y3-4) is pervertibles-1,3,5-trilinos group. In addition, as specific examples of the group (Y) is a tetravalent group can be specified (Y4-1)-(Y4-5) group. In addition, as a concrete example, when the group (Y) is a pentavalent group can be specified (Y5-1) group.

As a group (Y) is preferred group (Y3-1)-(Y3-4).

The compound (A) is a compound in which x is the number of groups (X) and z the number of groups (Z) is associated with the group (Y), where x is an integer of at least 3, z is an integer of at least 0, and (x+z) is equal to an integer at least 3. That is, the compound (A) is a compound in which at least three groups (X) associated with a group (Y) and (Z) may be associated with her.

As the compound (A) has at least three groups (X) with linear parfocality communication (fragment-(CF2CF2O)b-" in the group (X)), the compound (A) has prekrasnuu elasticity at low temperature. In addition, the group (X) is U (hereinafter called reactive group (U)) as a monovalent group having at least one element selected from the group consisting of unsaturated hydrocarbon, bromine atom and iodine atom. Therefore, during the cross-linking treatment fluorine-containing elastomer composition containing the compound (A), the compound (A) is associated with fluoro and optionally three-dimensional crosslinks with him, resulting in the compound (A) is stably embedded in silicone elastomer. Accordingly, it is possible to prevent the selection of compounds (A) on the surface of the crosslinked silicone elastomer in the quality of the final product and you can save excellent low-temperature characteristics over a long period. In addition, because in this way it is possible to prevent the selection of compounds (A), it is possible to prevent contamination of the form during molding, surface hardness, etc. in Addition, the compound (A) is associated with fluoro and optionally three-dimensional crosslinks with him, in consequence of which it is possible to improve the basic properties, such as strength, hardness, modulus, or residual deformation during compression of the resulting crosslinked rubber product.

In the compound (A) x is an integer of at least 3, preferably from 3 to 100, particularly preferably from 3 to 8. In addition, z is an integer of at least 0, p is edocfile from 0 to 10, more preferably from 0 to 1, particularly preferably 0. Moreover, (x+z) is an integer of at least 3, preferably from 3 to 110, more preferably from 3 to 9, particularly preferably 3 or 4. When x is at least 3, the compound (A) may be a three-dimensional image stitched in the silicone elastomer.

That is, the compound (A) preferably is a compound expressed by the following formula (A1):

(X)x1Y (A1)

where x1 is the number 3 or 4.

As specific examples of the group (Y) is a trivalent group in the compound (A) can be mentioned compounds (A3-1)-(A3-4). In addition, as specific examples of the group (Y) is a tetravalent group, can be mentioned compounds (A4-1)-(A4-10). Among them, from the viewpoint of the balance between shivamurthy and low-temperature characteristics, (A3-1), (A4-1) or (A4-2) is preferred.

Preferred specific examples of the compound (A) may be a compound expressed by the following formula (A2):

where each of b1, b2 and b3, which are independent of each other, is equal to an integer from 1 to 20, preferred is entrusted integer from 1 to 10.

Srednekislye molecular weight (hereinafter also referred to as Mn) of the compound (A) is preferably from 500 to 100,000, more preferably from 1000 to 20000. If Mn is less than 500, the low-temperature characteristics may be insufficient, and if Mn exceeds 100000, stevenot may deteriorate.

The ratio (hereinafter, also denoted by Mw/Mn) weighted average molecular weight (hereinafter also referred Mw) to srednekamennogo molecular weight (Mn) of the compound (A) is preferably from 1.0 to 2.0.

In addition, in the present invention, the Mn and Mw are values measured by gel permeation chromatography (hereinafter referred to GPC), and Mw/Mn is a value defined by Mn and Mw, as measured by TNX.

The compound (A) can be obtained, for example, so that the connection (AO) is obtained using the method described in WO 2005/068534, and the end connections are converted using a known method. In the compound (AO) Rddenotes a lower alkyl group.

(RdOC(O)-CF2O(CF2CF2O)b-)x(Z)zY (AO)

In addition, the value of x or z may vary depending on the reaction conditions phase fluorination upon receipt (AO) (e.g., [0043] and [0044] in JP-A-2009-197210). Accordingly, there is a case where the compound (A) contains a compound where x ravneet is, at most 2. In this case, the connection, where x is equal to at most 2, is not included in the compound (A) of the present invention, but during use of the compound (A) as a co-crosslinking agent fluoro compound (A) can be used directly without separation of compounds, where x is equal to at most 2.

In addition, in this description, since the compound (A) has at least x reactive groups (U), the compound (A) will sometimes be referred to as h-functional compound. The compound (A) will be called, for example, trifunctionally connection, when x is 3, or tetrafunctional connection, when x is 4. In addition, the connection, where x is at most 2, as a by-product, will also be referred to as monofunctional compound or a bifunctional compound.

The compound (A) obtained by the reaction can be used directly in the form of a solution after the reaction, or it may be used after removing the unnecessary solvent and starting materials, for example, by concentration. In addition, can be cleared. As a means of cleaning the washing water or an organic solvent, which causes phase separation of the compounds (A), removing, for example, metal impurities or niennah impurities using ion-adsorbing polymer, supercritical extraction or column chromatography may be mentioned, and these tools can be combined.

In the stitching fluorine-containing elastomer composition of the present invention, the content of compound (A) is preferably from 1 to 50 mass parts, more preferably from 5 to 50 mass parts, most preferably from 10 to 50 mass parts per 100 mass parts of the silicone elastomer. If the content of compound (A) is too low, the elasticity at low temperature could not be improved in some cases, and therefore, the effect of improving low-temperature characteristics can be small. If the content of compound (A) is too high, the compound (A) has a tendency to stand out from the rubber product after stitching. If the content of compound (A) is from 1 to 50 mass parts per 100 mass parts of silicone elastomer, the amount of the crosslinking becomes high, and the crosslinked rubber product excellent in low-temperature characteristics can be easily obtained.

[Fluoro]

Now will be described fluoropolymer elastomer used for the stitching fluorine-containing elastomer composition of the present invention.

The silicone elastomer is not particularly limited. The copolymer vinylidenefluoride/hexaferrite, a copolymer of vinylidenefluoride/tetrafluoroethylene/hexaferrite, the copolymer is of incidentid/chlorotrifluorethylene, a copolymer of tetrafluoroethylene/propylene, a copolymer of tetrafluoroethylene/propylene/vinylidenefluoride, copolymer of hexaferrite/ethylene, a copolymer of tetrafluoroethylene/perfluoroalkyl vinyl ether or a copolymer of vinylidenefluoride/tetrafluoroethylene/perfluoroalkyl vinyl ether can be, for example, mentioned. One or more of them may be used in combination. Among them, a copolymer of tetrafluoroethylene/propylene, a copolymer of vinylidenefluoride/tetrafluoroethylene/hexaferrite or a copolymer of tetrafluoroethylene/perfluoroalkyl vinyl ether is preferably used because of their excellent chemical resistance.

The fluorine content in the silicone elastomer is preferably at least 40 wt.%, more preferably, at least 50 wt.%, most preferably, at least 55% wt. Fluoropolymer elastomer having a fluorine content of at least 40 wt.%, can give a crosslinked rubber product excellent in heat resistance, chemical resistance, electrical insulating properties or resistance to the pair.

As preferred examples of the silicone elastomer, which is present on the market, "AFLAS150P" (trademark, product of Asahi Glass Company, Limited, a copolymer of tetrafluoroethylene/propylene) may be, for example, mentioned.

[Organic peroxide]

Stitched fluorine-containing elastomer compositionbased of the invention may additionally contain an organic peroxide. Any organic peroxide may be used if it can easily generate radicals when heated. Among them, it is preferable to use an organic peroxide having a temperature at which the half-life is equal to one minute, from 130 to 220°C. as specific examples of the 1,1-di(tert-guxiproxy)-3,5,5-trimethylcyclohexane, 2.5-dimethylhexane-2,5-dihydroperoxide, di-tert-butylperoxide, tert-butylcumylperoxide, dicumylperoxide, α,α'-bis(tert-BUTYLPEROXY)-p-diisopropylbenzene, 2,5-dimethyl-2,5-di(tert-BUTYLPEROXY)hexane, 2,5-dimethyl-2,5-di(tert-BUTYLPEROXY)hexyne-3, Dibenzoyl peroxide, tert-butylperoxybenzoate, 2,5-dimethyl-2,5-di(benzoylperoxy)hexane, tert-butylperoxybenzoate acid or tert-exelperceirrimageyoy can be, for example, mentioned, and α,α'-bis(tert-BUTYLPEROXY)-p-diisopropylbenzene is preferred. As the organic peroxide, one or more of them may be used in combination.

The content of the organic peroxide is preferably from 0.1 to 5 mass parts, more preferably from 0.2 to 4 mass parts, most preferably from 0.5 to 3 mass parts per 100 mass parts of the silicone elastomer. When the content is within this range, the crosslinking efficiency of the organic peroxide is in the high, consequently it is also possible to suppress the amount of unproductive decomposition. However, when stitched fluorine-containing elastomer composition is subjected to a crosslinking treatment by irradiation of radioactive rays, there is no need to enter the organic peroxide.

[Other components]

In the stitching fluorine-containing elastomer composition of the present invention polyfunctional compound can optionally be entered as a co-crosslinking agent. The polyfunctional compound may represent, for example, treelistener, triallylisocyanurate, the fluoropolymer of triallylisocyanurate, trimethylsilane, 1,3,5-triacilglycerides-1,3,5-triazine, triallylamine, m-phenylenedimaleimide, p-financiacion, p,p'-dibenzoylhydrazine, dipropyleneglycol, diallylphthalate, N,N',N",N"'-Tetraethylenepentamine or oligomer containing the vinyl group of the siloxane, such as polymethylvinylsiloxane or polymethylvinylsiloxane. Among them polyallyl compound is preferred, treelistener, triallylisocyanurate or trimethylsilane more preferred, and triallylisocyanurate even more preferred. Using the compound (A), triallylisocyanurate in combination, it is possible to more effectively suppress the selection of custom made rubber products. As the e polyfunctional compounds one or more of them may be used in combination. In the case when introducing a polyfunctional compound, its content is preferably from 0.1 to 20 mass parts, more preferably from 0.2 to 10 mass parts per 100 mass parts of the compound (A). If the content of the polyfunctional compound is less than 0.1 mass parts, the effect of adding a polyfunctional compound can hardly be obtained, and if it exceeds 20 mass parts, the formability is likely to deteriorate.

Stitched fluorine-containing elastomer composition of the present invention may contain a filler. By introducing the filler can improve the strength of the resulting crosslinked rubber product. The filler may preferably be used soot. Any carbon black may be used, if carbon black is used for blending with rubber. As specific examples may be mentioned furnace carbon black, acetylene black, thermal black, channel gas carbon black or graphite. Among them, the furnace carbon black is more preferable, and as a specific preferred example of such a sort as HAF-LS, HAF, HAF-HS, FEF, GPF, APF, SRF-LM, SRF-HM / MT, and the most preferred MT.

When injected filler, its content is preferably from 5 to 100 mass parts, more preferably from 10 to 50 mass parts per 100 mass parts of fork is Echuca. If the content of the filler is less than 5 mass parts, the effect of addition of filler can hardly be obtained, and if the content exceeds 100 mass parts, the property of elongation crosslinked rubber product may deteriorate. When the content of the filler is in the above range, the balance between strength and elongation of the obtained crosslinked rubber product becomes good.

Stitched fluorine-containing elastomer composition of the present invention may contain other additives, such as reinforcing material, technological additive, a lubricant, a lubricating agent, a flame arrester, an antistatic agent or dye.

The above reinforcing material may be, for example, a silicone elastomer, such as polytetrafluoroethylene or a copolymer of ethylene/tetrafluoroethylene, fiberglass, carbon fiber or white soot. If the content of the reinforcing material, its content is preferably from 5 to 200 mass parts, more preferably from 10 to 100 mass parts per 100 mass parts of the silicone elastomer.

The above technological additive may be, for example, alkali metal salt of higher fatty acid and stearate or laurate is preferred. In the case of technological additive content is preferably from 0.1 to 20 mass the parts, more preferably 0.2 to 10 mass parts, most preferably 1 to 5 mass parts per 100 mass parts of the silicone elastomer. If the number of process additives becomes too large, on the surface of the crosslinked rubber product may be formed by coating, the hardness of the crosslinked rubber product may be too high, or chemical resistance, or resistance to vapor may be low. If the number of process additive is too small, the tensile strength of the crosslinked rubber product may be much lower, or change in elongation or tensile strength after test thermal aging can be significantly large.

(Preparation method for stapling a fluorine-containing elastomer composition)

Cooking method for stapling a fluorine-containing elastomer composition of the present invention is not particularly limited and may be a known manner. Preferred is a method of mixing the silicone elastomer, the above compounds (A) and, if required, an organic peroxide, carbon black or other additives using a kneading machine such as a two-shaft machine, a Bunbury mixer or Mesilla. In addition, you can also use a cooking method in which the above respective components are dissolved and dispersed in the solvent with subsequent AC is sevanam in this state.

The order of mixing the above respective components is not particularly limited, but preferably, when the first components that little reactive or not decompose under heat dissipation, sufficiently mixed with the silicone elastomer, and then, for example, organic peroxide as the component that readily reacts or decomposes add thereto, followed by stirring. During mixing, it is preferable to cool kneading machine with water, keeping the temperature in the range from 80 to 120°C as the temperature at which the crosslinking reaction does not proceed.

(Cross-linked rubber product)

Crosslinked rubber product of the present invention can be obtained by forming the stitching fluorine-containing elastomer composition of the present invention by a known method such as extrusion molding, injection molding, injection molding extrusion or press molding, followed by sewing. Forming and stapling can be performed simultaneously, or they may respectively be performed separately at different stages.

For example, the cavity shape having one or more crosslinked rubber products, fill stitched fluorine-containing elastomer composition comprising an organic peroxide, and this form is heated, getting stitched rubber is Adelie (primary cross-linked product). The heating temperature is preferably from 130 to 220°C., more preferably 140 to 200°C., most preferably from 150 to 180°C. in Addition, if required, also preferably, when it is crosslinked rubber product (primary cross-linked product) optionally heated using, for example, a furnace that uses electricity, heated air or steam as a heat source, performing stapling (hereinafter also referred to as secondary crosslinking), which is preferred. By performing the secondary stitching the remainder of the organic peroxide contained in the crosslinked rubber product, decompose and uletuchivayas to reduce. The heating temperature during the secondary crosslinking is preferably from 150 to 280°C., more preferably from 180 to 260°C., most preferably from 200 to 250°C. the time of the secondary crosslinking is preferably from 1 to 48 hours, more preferably from 4 to 24 hours.

In addition, stitched fluorine-containing elastomer composition of the present invention can also be sewn by applying ionizing radiation such as electron beam or γ-rays. To obtain a crosslinked rubber product by applying ionizing radiation, for example, by the method of dilution and dispersion stitched fluorine-containing elastomer composition of the present invention in proper races is varicela, premises resulting solution of suspension in the form, and then drying, and then applying ionizing radiation to obtain a crosslinked rubber product, or a method of forming stitched fluorine-containing elastomer composition of the present invention in the previously described form and then applying ionizing radiation to obtain a crosslinked rubber product, for example, can be mentioned. Exposure dose of ionizing radiation can be selected in a suitable manner, but preferably is from 1 to 300 kGy, preferably from 10 to 200 kGy.

Crosslinked rubber product of the present invention can suitably be used in a wide range of elements such as a sealing material such as o-ring, sheet, strip, seal or bearing seal, diaphragm, damping material, the vibration absorber, the coating material of the wire, industrial belt, tube/hose and sheet, in a wide space such as a transport vehicle such as a car, a common tool or electrical apparatus. Among them it may appropriately be used as a sealing material such as o-ring, sheet, strip, seal or bearing seal, from the viewpoint of excellent elasticity at low temperature, and, in addition, from the point of view of the closing the ACLs basic properties such as strength, hardness, modulus, or residual deformation under compression.

EXAMPLES

Now the present invention will be described in detail with reference to examples, but it should be understood that the present invention is in no way limited to these specific examples.

[Materials]

Mix the components used in the subsequent examples and comparative examples, the following.

(1) silicone elastomer

Polymer 1: Bipolymer tetrafluoroethylene/perfluoroalkyl vinyl ether (trade mark: AFLAS PFE1000, manufactured by Asahi Glass Company, Limited, peroxide type crosslinking, fluorine content: 72% wt.)

Polymer 2: terpolymer tetrafluoroethylene/propylene/vinylidenefluoride (brand: AFLAS 200R manufactured by Asahi Glass Company, Limited, peroxide type crosslinking, fluorine content: 60% wt.)

Polymer 3: Bipolymer tetrafluoroethylene/propylene (brand: AFLAS 100S, manufactured by Asahi Glass Company, Limited, peroxide type crosslinking, fluorine content: 57% wt.)

(2) Co-crosslinking agent

Joint crosslinking agent 1: composition having as a main component the compound (A2') derived in the following example, cooking, and having a Mn 2900 and Mw/Mn 1,14.

TAITZ: Triallylisocyanurate (manufactured by Nippon Kasei Chemical Co., Ltd.)

(3) Organic peroxide

Terbutyl R: α,α'-bis(tert-BUTYLPEROXY)-p-diisopropyl the benzene (brand: PERKADOX 14, manufactured by NOF CORPORATION)

PERHEXA 25B: 3,5-dimethyl-2,5-di-tert-butylperoxide (brand: PERHEXA 25B, manufactured by NOF CORPORATION)

(4) Filler

MT carbon: carbon black (brand: MT carbon, manufactured by CANCARB)

(5) Technological additive

NONSOUL SN-1: sodium stearate (manufactured by NOF CORPORATION)

(Preparation of joint cross-linking agent)

The inner part 100 ml round flask, equipped and placed in it a stirrer, sufficiently replaced by nitrogen. to 20.0 g of the composition containing the following compound (A0-1) as a main component, and 20 g of dichloropentafluoropropane placed in this round flask under vigorous stirring. After one hour the mixture of 1.5 g of CH2=CHCH2NH2and 20 g of dichloropentafluoropropane was slowly added dropwise over 0.5 hours from the dropping funnel, located in the upper part of round-bottom flask. After completion of the addition the contents of the flask were heated to 50°C., was continuously stirred for 6 hours and then cooled to room temperature.

The obtained crude liquid was concentrated by using an evaporator, and the residue was twice washed with 0.1 l of n-hexane, obtaining of 18.8 g of the composition in the form of a colourless liquid at room temperature. This composition was such that at least about 99.9 mol%. "-C(O)och2CH3" vysheukazannoe the th connection (A0-1) was converted into a "-C(O)NHCH 2CH=CH2"and the following compound (A2') was the main component. In addition, the average value of b1+b2+b3 in the composition having the formula (A2') as a main component, was 21.1 in the NMR measurements. This song called joint cross-linking agent 1.

The compound (A2') were subjected to NMR analysis, HPLC analysis and GPC analysis under conditions of room temperature (25°C), which was proven by the formation of compound (A2').

<NMR analysis>

As a standard substance1H-NMR (300,4 MHz) with tetramethylsilane was used. In addition, as a standard substance19F-NMR (282,7 MHz) used CFCl3. In addition, the solvent used CCl2FCClF2if not specified otherwise.

<HPLC analysis>

The compositional ratio of the compounds in this composition was measured using HPLC analyzer (Prominence, manufactured by Shimadzu Corporation) under the following conditions. More specifically, in each run of the HFIP concentration in the mobile phase was gradually increased from 0% to 100% and analyzed the mass ratio of the compounds in the discharge of the composition.

Analytical column: a column with a stationary phase of silica (SIL-gel, manufactured by YMC Co., Ltd.)

Mobile phase: Dichloropentafluoropropane (ASAHIKLIN AK-225G, manufactured by Asahi Glass Company, Limited) and HFIP

The velocity of the flow of the mobile phase (1.0 ml/min

The column temperature: 37°C

Detector: Evaporative light scattering detector

<GPU analysis>

Srednekamennogo molecular weight (Mn) and the weighted average molecular weight (Mw) was measured using the GPU according to JP-A-2001-208736 in the following conditions, and determine the Mw/Mn.

Mobile phase: a Mixture of solvents dichloropentafluoropropane (ASAHIKLIN AK-225SEC mark 1, manufactured by Asahi Glass Company, Limited) and hexafluoroisopropyl alcohol (dichloropentafluoropropane/ hexafluoroisopropyl alcohol = 99/1 by volume)

Analytical column: two columns connected in series Plgel MIXED-E (manufactured by Polymer Laboratories)

Standard samples of molecular weight: four performalite having a Mw/Mn less than 1.1, and a molecular weight of from 2000 to 10000, and one parfocality having Mw/Mn of at least 1.1 and a molecular weight of 1300

The flow rate of the mobile phase (1.0 ml/min

The column temperature: 37°C

Detector: Evaporative light scattering detector

In the HPLC analysis, it was found that the resulting joint crosslinking agent 1 had a composition containing 7.0% by weight. monofunctional compounds, 30,8% wt. bifunctional compounds, 42,9% wt. trifunctional compounds (A2'), 18.1% of the wt. tetrafunctional connection and 1.2% wt. compounds having more than 4 functional groups. Accordingly, the proportion of the compound (A) having 3 or more functional groups, which is effective in the three-dimensional crosslinking, was 62,2% wt. Monofunctional compound and a bifunctional compound were compounds having a small number of functional groups that are formed as by-products during fluorination, and, even though these compounds are not compound (A), this joint crosslinking agent 1 used directly without separation of these compounds.

In the HEP analysis average molecular weight (Mn) of the joint linking agent 1 was $ 2900, and Mw/Mn was 1,14. In addition, it was shown that the joint cross-linking agent 1 had no structure-OCF2O-.

The result of NMR analysis, the following results were obtained in the form of the spectrum1H-NMR spectrum and19F-NMR.

Range1H-NMR spectrum σ (h/million): 7,09, 5,92, 5,38-5,20, 3,72

Range19F-NMR spectrum σ (h/million): -543,0, -77,6, -88,2 - -92,0, -135,0 - -139,0

[Measurement of crosslinked rubber products]

The value of TR-10, the hardness (HS), tensile strength (TIn), elongation (EIn), the residual deformation under compression and 100% tensile stress (M100) crosslinked rubber products in each of the following examples and comparative examples was measured using the following methods.

Test low-temperature elastic retraction: According to JIS K, test low-temperature elastic tightening done is whether using measuring low-temperature elastic retraction (TR meter, manufactured by Ueshima Seisakusho Co., Ltd.), measuring the value of TR-10.

Hardness: According to JIS K, hardness (HS) was measured using test hardness Durometer of type a at 23°C. When the hardness is 60 to 90, the product is suitable as a sealing material.

Tensile strength: According to JIS K, tensile strength (TIn) was measured at 23°C. When the tensile strength (TIn) is at least 10 MPa, the product is suitable as a sealing material.

Elongation: According to JIS K, elongation (EIn) was measured at 23°C. When the elongation (EIn) is at least 160%, the product is suitable as a sealing material.

The residual strain in compression: According to JIS K, residual strain in compression was measured at 200°C for 70 hours.

100% tensile stress (modulus): According to JIS K, 100% tensile stress (M100) was measured at 23°C. When 100% tensile stress (M100) ranges from 2 to 17 MPa, the product is suitable as a sealing material.

Example 1

100 mass parts of the polymer 1, 1 mass part of PERHEXA 25B, 5 mass parts of a joint cross-linking agent 1, 20 mass parts of MT carbon and 1 mass part NONSOUL SN-1 were mixed using a twin-screw rolling machines, getting stitched peroxide silicone elastomer is a new composition. The composition was molded into a sheet of 100 mm × 100 mm × 2 mm by hot pressing at 170°C (primary crosslinking). Next, this sheet was placed in a gear oven for four hours at 250°C, performing a secondary binding.

From the obtained crosslinked rubber sheet was knocked four leaf samples using #3 weights, measuring the properties of the crosslinked rubber. In addition, according to JIS K prepared four test sample low-temperature elastic tightening, performing test low-temperature elastic retraction. The results are shown in table 1. This crosslinked rubber product has a hardness (HS) 61, tensile strength (TIn) of 19.8 MPa, elongation (EIn) 232%, 100% tensile stress (M100) 9,0 MPa, the residual deformation when compressed 30% and the amount of TR-10 to-7.6°C.

Examples 2-6 and comparative examples 1-3

Crosslinked rubber sheet was prepared in the same manner as in example 1, except that the respective components of the mixture were replaced as shown in table 1, and properties of crosslinked rubber products was measured in the same manner as described above.

As shown in table 1, made of rubber products in examples 1-6 have such physical properties of the normal state, as cross-linked rubber products in comparative examples 1-3, the low value of the ER-10 and excellent flexibility at low the temperature. In addition, since the amount added of the joint linking agent 1 increases, the value of the TR-10 is reduced, and elasticity at low temperature is improved.

On the other hand, custom made rubber products in comparative examples 1-3, which was obtained by crosslinking the fluorine-containing elastomer composition not containing joint cross-linking agent 1 (compound (A2)), were such that the value of TR-10 each crosslinked rubber product obtained using the same silicone elastomer was higher and elasticity at low temperatures was poor compared with examples 1-6.

Applicability in industry

Crosslinked rubber product of the present invention can suitably be used in a wide range of elements such as a sealing material such as o-ring, sheet, strip, seal or bearing seal, diaphragm, damping material, the vibration absorber, the coating material of the wire, industrial belt, tube/hose and sheet, in a wide space such as a transport vehicle such as a car, a tool or electrical system.

A full description of Japanese patent application No. 2009-229424 registered 1 October 2009, including the description, the claims and the invention is incorporated here by reference in all fullness is.

1. Stitched fluorine-containing elastomer composition comprising a silicone elastomer and a compound expressed by the following formula (A):
,
where X represents a group expressed by the following formula (X), Z represents a group expressed by the following formula (Z), Y denotes (x+z) valent perforacion hydrocarbon group or such a group having an etheric oxygen atom, embedded between its carbon atoms, x is an integer of at least 3, z is an integer of at least 0, and x+z is an integer of at least 3

where U denotes a monovalent group having at least one element selected from the group consisting of unsaturated hydrocarbon, bromine atom and iodine atom, RFrepresents C1-20linear performanceline group or such a group having an etheric oxygen atom, embedded between its carbon atoms, and a is an integer from 0 to 20, b is an integer from 1 to 200, and C is an integer from 3 to 200, where the content of the compound expressed by formula (A) is from 1 to 50 wt.h. on 100 wt.h. fluoro.

2. Stitched fluorine-containing elastomer composition under item 1, where the compound expressed by the formula (A) is a compound expressed by the following formula (A1):

where x1 is the number 3 or 4.

3. The stitching is I a fluorine-containing elastomer composition according to p. 2, where x1 in the formula (A1) is equal to 3 and Y represents any of the groups (Y3-1)-(Y3-4) expressed by the following formula:
.

4. Stitched fluorine-containing elastomer composition under item 1, where the compound expressed by the formula (A) is a compound expressed by the following formula (A2):

where each of b1, b2 and b3, which are independent of each other, is an integer from 1 to 20.

5. Stitched fluorine-containing elastomer composition under item 1, where the compound expressed by the formula (A), has srednekamennogo molecular weight (MP) of from 500 to 100000.

6. Stitched fluorine-containing elastomer composition under item 1, where the compound expressed by the formula (A) has a ratio (Mw/Mn) weighted average molecular weight Mw to srednekamennogo molecular weight MP of 1.0 to 2.0.

7. Stitched fluorine-containing elastomer composition under item 1, where the silicone elastomer is at least one element selected from the group consisting of a copolymer of tetrafluoroethylene/propylene copolymer vinylidenefluoride/tetrafluoroethylene/hexaferrite and a copolymer of tetrafluoroethylene/perfluoroalkyl vinyl ether.

8. Stitched fluorine-containing elastomer composition under item 1, which further comprises an organic peroxide.

9. Crosslinked rubber product formed by stitching the stitching fluorine-containing elastomer composition under item 1.

10 Crosslinked rubber product under item 9, which is a sealing material.



 

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