WO2023042727A1 - ゴム組成物、加硫物、及び加硫成形体 - Google Patents
ゴム組成物、加硫物、及び加硫成形体 Download PDFInfo
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- WO2023042727A1 WO2023042727A1 PCT/JP2022/033588 JP2022033588W WO2023042727A1 WO 2023042727 A1 WO2023042727 A1 WO 2023042727A1 JP 2022033588 W JP2022033588 W JP 2022033588W WO 2023042727 A1 WO2023042727 A1 WO 2023042727A1
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- Prior art keywords
- rubber
- chloroprene
- rubber composition
- mass
- parts
- Prior art date
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- 239000005060 rubber Substances 0.000 title claims abstract description 214
- 239000000203 mixture Substances 0.000 title claims abstract description 126
- 239000000178 monomer Substances 0.000 claims abstract description 64
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000004593 Epoxy Substances 0.000 claims abstract description 55
- 150000002825 nitriles Chemical class 0.000 claims abstract description 27
- 239000003795 chemical substances by application Substances 0.000 claims description 45
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 42
- -1 unsaturated fatty acid ester Chemical class 0.000 claims description 25
- 238000000465 moulding Methods 0.000 claims description 24
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 16
- 239000000945 filler Substances 0.000 claims description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 7
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 6
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- 239000003822 epoxy resin Substances 0.000 claims description 5
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- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 abstract description 95
- 238000006116 polymerization reaction Methods 0.000 description 26
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- 238000004073 vulcanization Methods 0.000 description 20
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- 238000004519 manufacturing process Methods 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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- 125000003700 epoxy group Chemical group 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 9
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- 239000006057 Non-nutritive feed additive Substances 0.000 description 8
- 239000006087 Silane Coupling Agent Substances 0.000 description 8
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 8
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- 238000012360 testing method Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001451 organic peroxides Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 3
- GWQOYRSARAWVTC-UHFFFAOYSA-N 1,4-bis(2-tert-butylperoxypropan-2-yl)benzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=C(C(C)(C)OOC(C)(C)C)C=C1 GWQOYRSARAWVTC-UHFFFAOYSA-N 0.000 description 3
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- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000002174 Styrene-butadiene Substances 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000011088 calibration curve Methods 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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- 125000005647 linker group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
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- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 2
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- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
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- RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical class C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 2
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- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
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- 238000004458 analytical method Methods 0.000 description 2
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- 229910052799 carbon Inorganic materials 0.000 description 2
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- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- RKQOSDAEEGPRER-UHFFFAOYSA-L zinc diethyldithiocarbamate Chemical compound [Zn+2].CCN(CC)C([S-])=S.CCN(CC)C([S-])=S RKQOSDAEEGPRER-UHFFFAOYSA-L 0.000 description 1
- PGNWIWKMXVDXHP-UHFFFAOYSA-L zinc;1,3-benzothiazole-2-thiolate Chemical compound [Zn+2].C1=CC=C2SC([S-])=NC2=C1.C1=CC=C2SC([S-])=NC2=C1 PGNWIWKMXVDXHP-UHFFFAOYSA-L 0.000 description 1
- NEYNBSGIXOOZGZ-UHFFFAOYSA-L zinc;butoxymethanedithioate Chemical compound [Zn+2].CCCCOC([S-])=S.CCCCOC([S-])=S NEYNBSGIXOOZGZ-UHFFFAOYSA-L 0.000 description 1
- KMNUDJAXRXUZQS-UHFFFAOYSA-L zinc;n-ethyl-n-phenylcarbamodithioate Chemical compound [Zn+2].CCN(C([S-])=S)C1=CC=CC=C1.CCN(C([S-])=S)C1=CC=CC=C1 KMNUDJAXRXUZQS-UHFFFAOYSA-L 0.000 description 1
- SZNCKQHFYDCMLZ-UHFFFAOYSA-L zinc;propan-2-yloxymethanedithioate Chemical compound [Zn+2].CC(C)OC([S-])=S.CC(C)OC([S-])=S SZNCKQHFYDCMLZ-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4035—Hydrazines; Hydrazides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L11/00—Compositions of homopolymers or copolymers of chloroprene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2311/00—Characterised by the use of homopolymers or copolymers of chloroprene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
Definitions
- the present invention relates to rubber compositions, vulcanizates, vulcanized moldings, and the like.
- Chloroprene rubber is excellent in various properties, and is used in a wide range of fields such as automobile parts, adhesives, various industrial rubber parts, etc., taking advantage of these properties.
- the rubber compositions described in Patent Documents 1 to 3 below are known as technologies that can use chloroprene rubber.
- JP 2016-23191 A JP 2012-111899 A JP-A-9-268239
- the present invention has been made in view of such circumstances, and provides a rubber composition that can improve the scorch time of an unvulcanized product, and the hardness, tensile strength, and cold resistance of a vulcanized product in a well-balanced manner. It provides
- a rubber composition comprising a chloroprene rubber having an unsaturated nitrile monomer unit content of less than 25% by mass and an epoxy compound having a weight average molecular weight of more than 100 and less than 900,
- a rubber composition containing 0.1 to 25 parts by mass of the epoxy compound with respect to 100 parts by mass of the chloroprene rubber.
- a vulcanizate of the rubber composition described above there is provided a vulcanized molding using the vulcanizate described above.
- the present inventors have found that by including a specific type of chloroprene-based rubber and an epoxy-based compound having a specific molecular weight and specifying the blending amount of the epoxy-based compound, an unvulcanized product can be obtained.
- the inventors have found that a rubber composition can improve the scorch time, and the hardness, tensile strength, and cold resistance of the vulcanizate in a well-balanced manner, and have completed the present invention.
- a rubber composition comprising a chloroprene-based rubber having an unsaturated nitrile monomer unit content of less than 25% by mass and an epoxy-based compound having a weight average molecular weight of more than 100 and less than 900, wherein the chloroprene-based A rubber composition containing 0.1 to 25 parts by mass of the epoxy compound per 100 parts by mass of rubber.
- the unsaturated nitrile monomer is acrylonitrile.
- the epoxy compound is at least one epoxy compound selected from an alicyclic epoxy compound, an epoxy resin comprising a copolymer of epichlorohydrin and bisphenol, and an epoxidized unsaturated fatty acid ester.
- [5] The rubber composition according to any one of [1] to [4], which contains 5 parts by mass or more of a curing agent with respect to 100 parts by mass of the epoxy compound.
- the rubber composition according to the present invention can provide vulcanizates and vulcanized molded articles having sufficient scorch time and excellent hardness, tensile strength and cold resistance. Furthermore, the obtained vulcanizates and vulcanized moldings have a sufficient scorch time, and are therefore excellent in workability and storage stability. In addition, the obtained vulcanizate and vulcanized molded product have excellent mechanical strength, weather resistance, chemical resistance, heat resistance, etc. possessed by chloroprene rubber, and furthermore have improved hardness, tensile strength, and By having cold resistance, it can be used as various members that require these properties. Examples include rubber parts for automobiles (for example, sealing materials for automobiles), hoses, rubber moldings, gaskets, rubber rolls, industrial cables, industrial conveyor belts, sponges and the like.
- the rubber composition according to the present invention contains a chloroprene rubber having an unsaturated nitrile monomer unit content of less than 25% by mass and an epoxy compound having a weight average molecular weight of more than 100 and less than 900,
- the epoxy compound is contained in an amount of 0.1 to 25 parts by mass with respect to 100 parts by mass of the chloroprene rubber.
- the present invention by including a specific type of chloroprene rubber and an epoxy compound having a specific molecular weight, and specifying the amount of the epoxy compound, the scorch time of the unvulcanized product and the It is possible to improve the hardness, tensile strength, and cold resistance of the sulfide in a well-balanced manner.
- a rubber containing a chloroprene-based polymer is shown.
- the chloroprene-based polymer include chloroprene homopolymers and chloroprene copolymers (copolymers of chloroprene and a monomer that can be copolymerized with chloroprene).
- the polymer structure of the chloroprene-based polymer is not particularly limited.
- 2-chloro-1,3-butadiene may contain a small amount of 1-chloro-1,3-butadiene as an impurity.
- 2-Chloro-1,3-butadiene containing such a small amount of 1-chloro-1,3-butadiene can also be used as the chloroprene monomer in the present embodiment.
- a chloroprene-based rubber according to one embodiment of the present invention includes a rubber that is a chloroprene-based rubber having an unsaturated nitrile monomer unit content of less than 25% by mass.
- the chloroprene-based rubber according to one embodiment of the present invention has a content of unsaturated nitrile monomer units of less than 25% by mass when the rubber is 100% by mass, and a content of unsaturated nitrile monomer units is preferably 1% by mass or more and less than 25% by mass.
- the content of unsaturated nitrile monomer units in the chloroprene-based rubber according to one embodiment of the present invention is, for example, 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24% by mass, less than 25% by mass and within a range between any two of the numerical values exemplified here There may be.
- the obtained rubber composition has sufficient cold resistance.
- the obtained rubber composition has sufficient oil resistance, hardness, tensile strength, and cold resistance. It is possible to obtain a vulcanized molded article having an excellent balance of
- Unsaturated nitriles include acrylonitrile, methacrylonitrile, ethacrylonitrile, phenylacrylonitrile and the like.
- An unsaturated nitrile can be used individually by 1 type or in combination of 2 or more types.
- the unsaturated nitrile may contain acrylonitrile from the viewpoint of easily obtaining excellent moldability, and from the viewpoint of easily obtaining excellent breaking strength, breaking elongation, hardness, tear strength, and oil resistance in the vulcanized molded product. preferable.
- the content of unsaturated nitrile monomer units contained in the chloroprene-based rubber can be calculated from the content of nitrogen atoms in the chloroprene-based rubber. Specifically, the content of nitrogen atoms in 100 mg of chloroprene-based rubber is measured using an elemental analyzer (Sumigraph 220F: manufactured by Sumika Chemical Analysis Service, Ltd.), and the content of structural units derived from unsaturated nitrile monomers You can calculate the amount. Elemental analysis can be measured under the following conditions. For example, the electric furnace temperature is set to 900° C. for the reactor, 600° C.
- the column temperature is 70° C.
- the detector temperature is 100° C.
- oxygen as the combustion gas is 0.2 mL/min
- helium is 80 mL/min as the carrier gas. to flow.
- a calibration curve can be constructed using aspartic acid (10.52%) with a known nitrogen content as a standard.
- the chloroprene-based rubber according to one embodiment of the present invention preferably contains 60 to 100% by mass of chloroprene monomer units with respect to 100% by mass of rubber.
- the content of chloroprene monomer units in the chloroprene-based rubber is, for example, 60, 65, 70, 75, 80, 85, 90, 95, 99, 100% by mass. It may be in the range between.
- the chloroprene-based rubber according to one embodiment of the present invention can also have monomer units other than the chloroprene monomer and the unsaturated nitrile monomer.
- the monomer unit other than the chloroprene monomer and the unsaturated nitrile monomer is not particularly limited as long as it can be copolymerized with the chloroprene monomer or the chloroprene monomer and the unsaturated nitrile monomer.
- esters of (meth) acrylic acid (methyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, etc.), hydroxyalkyl (meth) acrylate (2-hydroxymethyl (meth) acrylate , 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, etc.), 2,3-dichloro-1,3-butadiene, 1-chloro-1,3-butadiene, butadiene, isoprene, ethylene, styrene , sulfur and the like.
- the chloroprene-based rubber according to one embodiment of the present invention can contain 0 to 20% by mass of monomer units other than the chloroprene monomer and the unsaturated nitrile monomer when the rubber is 100% by mass. .
- the content of monomer units other than the chloroprene monomer and the unsaturated nitrile monomer in the chloroprene rubber is, for example, 0, 2, 4, 6, 8, 10, 12, 14, 16, 18, 20 mass. % and may be in a range between any two of the numbers exemplified here.
- the chloroprene-based rubber according to one embodiment of the present invention may consist of only chloroprene monomer units and unsaturated nitrile monomer units, and may consist of only chloroprene monomer units.
- the rubber composition according to the present invention can use chloroprene-based rubbers singly or in combination of two or more.
- the content of unsaturated nitrile monomer units contained in the two or more chloroprene-based rubbers contained in the rubber composition is preferably less than 25% by mass.
- the chloroprene-based polymer (chloroprene homopolymer, chloroprene copolymer, etc.) contained in the chloroprene-based rubber according to the present invention includes sulfur-modified chloroprene polymer, mercaptan-modified chloroprene polymer, xanthogen-modified chloroprene polymer, dithiocarbohydrate It may be a nato-based chloroprene polymer, a trithiocarbonate-based chloroprene polymer, a carbamate-based chloroprene polymer, or the like.
- the weight average molecular weight (Mw), number average molecular weight (Mn), and molecular weight distribution (molecular weight polydispersity, Mw/Mn) of the chloroprene rubber provide excellent hardness, tensile strength, and cold resistance in a well-balanced manner. From the viewpoint of simplicity, the following range may be used.
- the weight average molecular weight of the chloroprene rubber is 10 ⁇ 10 3 g/mol or more, 50 ⁇ 10 3 g/mol or more, 100 ⁇ 10 3 g/mol or more, 300 ⁇ 10 3 g/mol or more, and 400 ⁇ 10 3 g. /mol or more, or 450 ⁇ 10 3 g/mol or more.
- the weight average molecular weight of the chloroprene rubber is 5000 ⁇ 10 3 g/mol or less, 3000 ⁇ 10 3 g/mol or less, 2000 ⁇ 10 3 g/mol or less, 1000 ⁇ 10 3 g/mol or less, and 800 ⁇ 10 3 g. /mol or less, or 500 ⁇ 10 3 g/mol or less.
- the weight average molecular weight of the chloroprene rubber is 10 ⁇ 10 3 to 5000 ⁇ 10 3 g/mol, 100 ⁇ 10 3 to 2000 ⁇ 10 3 g/mol, or 300 ⁇ 10 3 to 1000 ⁇ 10 g/mol. It may be 3 g/mol.
- the number average molecular weight of the chloroprene rubber is 1 ⁇ 10 3 g/mol or more, 5 ⁇ 10 3 g/mol or more, 10 ⁇ 10 3 g/mol or more, 50 ⁇ 10 3 g/mol or more, and 100 ⁇ 10 3 g. /mol or more, or 130 ⁇ 10 3 g/mol or more.
- the number average molecular weight of the chloroprene rubber is 1000 ⁇ 10 3 g/mol or less, 800 ⁇ 10 3 g/mol or less, 500 ⁇ 10 3 g/mol or less, 300 ⁇ 10 3 g/mol or less, and 200 ⁇ 10 3 g. /mol or less, or 150 ⁇ 10 3 g/mol or less.
- the number average molecular weight of the chloroprene rubber is 1 ⁇ 10 3 to 1000 ⁇ 10 3 g/mol, 10 ⁇ 10 3 to 500 ⁇ 10 3 g/mol, or 50 ⁇ 10 3 to 300 ⁇ 10 g/mol. It may be 3 g/mol.
- the molecular weight distribution of the chloroprene rubber may be 1.0 or more, 1.5 or more, 2.0 or more, 2.5 or more, 3.0 or more, 3.2 or more, or 3.4 or more.
- the molecular weight distribution of the chloroprene rubber may be 10 or less, 8.0 or less, 5.0 or less, 4.0 or less, 3.8 or less, 3.5 or less, or 3.4 or less. From these viewpoints, the molecular weight distribution of the chloroprene rubber may be 1.0 to 10, 2.0 to 5.0, or 2.5 to 4.0.
- the weight average molecular weight (Mw) and number average molecular weight (Mn) of the chloroprene rubber can be obtained by measuring by gel permeation chromatography (GPC) and converting to polystyrene. It can be measured by the method described in .
- the method for producing the chloroprene-based rubber according to the present invention is not particularly limited. can.
- a chloroprene monomer or a monomer containing a chloroprene monomer and an unsaturated nitrile monomer is added with an emulsifier, a dispersant, a catalyst, a chain transfer agent, or the like. It is possible to obtain a latex containing a chloroprene-based polymer containing chloroprene monomer units by adding a polymerization terminator when an intended final conversion is reached by emulsion polymerization using an appropriate amount.
- unreacted monomers can be removed from the polymerization liquid obtained by the emulsion polymerization step.
- the method is not particularly limited, and includes, for example, a steam stripping method. Thereafter, the pH is adjusted, and the chloroprene-based rubber containing the chloroprene-based polymer can be obtained through conventional steps such as freezing and coagulation, washing with water, and drying with hot air.
- the polymerization initiator used for emulsion polymerization is not particularly limited, and known polymerization initiators generally used for emulsion polymerization of chloroprene can be used.
- polymerization initiators include potassium persulfate, ammonium persulfate, sodium persulfate, hydrogen peroxide, and organic peroxides such as t-butyl hydroperoxide.
- the emulsifier used for emulsion polymerization is not particularly limited, and known emulsifiers generally used for emulsion polymerization of chloroprene can be used.
- emulsifiers include alkali metal salts of saturated or unsaturated fatty acids having 6 to 22 carbon atoms, alkali metal salts of rosin acid or disproportionated rosin acid (eg, potassium rosinate), and formalin condensates of ⁇ -naphthalenesulfonic acid. and alkali metal salts (for example, sodium salts) of.
- the molecular weight modifier used for emulsion polymerization is not particularly limited, and known molecular weight modifiers generally used for emulsion polymerization of chloroprene can be used. compounds, trithiocarbonate-based compounds and carbamate-based compounds. Xanthogen-based compounds, dithiocarbonate-based compounds, trithiocarbonate-based compounds and carbamate-based compounds can be suitably used as the molecular weight modifier for the chloroprene-based rubber according to one embodiment of the present invention.
- the polymerization temperature and the final conversion rate of the monomers are not particularly limited, the polymerization temperature may be, for example, 0 to 50°C or 10 to 50°C.
- the polymerization may be carried out so that the final conversion of monomer is in the range of 40-95% by weight.
- the polymerization may be terminated by adding a polymerization terminator for terminating the polymerization reaction when the desired conversion is achieved.
- the polymerization terminator is not particularly limited, and known polymerization terminator generally used for emulsion polymerization of chloroprene can be used.
- Examples of the polymerization terminator include phenothiazine (thiodiphenylamine), 4-t-butylcatechol, 2,2-methylenebis-4-methyl-6-t-butylphenol and the like.
- the chloroprene-based rubber according to one embodiment of the present invention can be prepared, for example, by removing unreacted monomers by a steam stripping method, adjusting the pH of the latex, freezing and coagulating by a conventional method, washing with water, drying with hot air, etc. can be obtained through the process of
- Chloroprene-based rubbers are classified into mercaptan-modified type, xanthogen-modified type, sulfur-modified type, dithiocarbonate-based type, trithiocarbonate-based type and carbamate-based type according to the type of molecular weight modifier.
- Epoxy Compound The rubber composition according to the present invention contains an epoxy compound, that is, a compound having an epoxy group.
- Epoxy compounds are reactive plasticizers (hardening type plasticizer).
- Epoxy-based compounds include alicyclic epoxy compounds, epoxy resins composed of copolymers of epichlorohydrin and bisphenol, epoxidized unsaturated fatty acid esters, and diene-based polymers having epoxy groups (corresponding to chloroprene-based polymers). excluding compounds that do).
- the epoxy-based compound preferably contains one or more selected from the group consisting of an alicyclic epoxy compound, an epoxy resin composed of a copolymer of epichlorohydrin and bisphenol, and an epoxidized unsaturated fatty acid ester. .
- Examples of alicyclic epoxy compounds include compounds represented by the following formulas (1), (2), and (3).
- X can be any organic group, for example, an optionally substituted hydrocarbon group, an example being an optionally substituted alkyl group, and It can be an alkenyl group.
- the hydrocarbon group can include a carbonyl group, an ether group (ether bond), an epoxy group, and a group in which a plurality of these are linked.
- Y represents any single bond or linking group (a divalent group having one or more atoms).
- the linking group include divalent hydrocarbon groups (eg, alkylene groups), carbonyl groups, ether groups (ether bonds), epoxy groups, groups in which a plurality of these are linked, and the like.
- Z 1 and Z 2 can each independently be any organic group, for example, a hydrocarbon group optionally having a substituent, for example, an optionally substituent and an alkenyl group.
- the hydrocarbon group can include a carbonyl group, an ether group (ether bond), an epoxy group, and a group in which a plurality of these are linked.
- alicyclic epoxy compounds include 3′,4′-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, ⁇ -caprolactone-modified 3′,4′-epoxycyclohexylmethyl 3,4-epoxycyclohexanecarboxylate, 1-vinyl-3,4-epoxycyclohexane, di-2-ethylhexyl 4,5-epoxycyclohexane-1,2-dicarboxylate, di(9,10-epoxystearyl 4,5-epoxycyclohexane-1,2-dicarboxylate ) etc. can be mentioned.
- An epoxy resin composed of a copolymer of epichlorohydrin and bisphenol is represented by formula (4).
- n in formula (4) preferably satisfies 0 ⁇ n ⁇ 2.
- epoxidized unsaturated fatty acid esters examples include epoxidized fatty acid isobutyl and epoxidized fatty acid 2-ethylhexyl.
- the diene polymer having an epoxy group is preferably liquid at room temperature (25°C).
- the diene polymer having an epoxy group include aliphatic conjugated diene polymers having an epoxy group, such as polybutadiene and polyisoprene; aromatic vinyl/aliphatic conjugated diene copolymers such as styrene-butadiene polymer (SBR). vinyl cyanide-conjugated diene copolymer such as acrylonitrile-butadiene polymer (NBR); hydrogenated SBR; and hydrogenated NBR.
- a diene-based polymer having an epoxy group may contain, for example, a compound represented by the following formula (5).
- the epoxy compound according to the present invention has a weight average molecular weight of more than 100 and less than 900.
- the weight average molecular weight of the epoxy compound according to the present invention is, for example, more than 100, 110, 150, 200, 250, 300, 350, 400, 450, 500, 550, 600, 650, 700, 750, 800, 850, less than 890, 900 and may be in the range between any two of the numbers exemplified herein.
- the scorch time of the unvulcanized product can be improved by setting the molecular weight of the epoxy compound to the above upper limit or less.
- the hardness, tensile strength, and cold resistance of the vulcanizate can be improved in a well-balanced manner.
- the weight average molecular weight can be obtained by measuring by gel permeation chromatography (GPC) and converting to polystyrene, and can be measured by the same method as the weight average molecular weight of the chloroprene polymer.
- the epoxy equivalent of the epoxy-based compound can be 100 to 500 g/eq.
- Epoxy equivalents are, for example, 100, 150, 200, 250, 300, 350, 400, 450, 500 g/eq, and may be within a range between any two of the values exemplified here.
- the rubber composition according to the present invention contains 0.1 to 25 parts by mass of an epoxy compound with respect to 100 parts by mass of chloroprene rubber.
- the content of the epoxy-based compound with respect to 100 parts by mass of the chloroprene-based rubber is, for example, 0.1, 0.5, 1, 5, 10, 15, 20, or 25 parts by mass. It may be within a range between two.
- the rubber composition according to one embodiment of the present invention may contain a curing agent.
- the curing agent is not particularly limited as long as it contributes to curing of the epoxy compound.
- Examples of curing agents include carboxylic acid hydrazide curing agents, amine curing agents, phenol curing agents, and acid anhydride curing agents. These can be used individually by 1 type or in combination of 2 or more types.
- the curing agent according to one embodiment of the present invention preferably contains a carboxylic acid hydrazide-based curing agent.
- the carboxylic acid hydrazide-based curing agent preferably contains any one selected from the group consisting of carboxylic acid hydrazides and carboxylic acid dihydrazides.
- carboxylic acid hydrazide curing agents include salicylic acid hydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, succinic acid dihydrazide, glutaric acid dihydrazide, adipic acid dihydrazide, suberic acid dihydrazide, azelaic acid dihydrazide, sebacic acid dihydrazide, tetrahydro phthalic acid dihydrazide, phthalic acid dihydrazide, dodecanedioic acid dihydrazide, isophthalic acid dihydrazide, and the like.
- the curing agent according to one embodiment of the present invention contains a carboxylic acid dihydrazide.
- the curing agent according to one embodiment of the present invention more preferably contains any one selected from the group consisting of dihydrazide isophthalate, dihydrazide sebacate, dihydrazide adipic acid, and dihydrazide dodecanedioate.
- the rubber composition according to one embodiment of the present invention may contain 5 parts by mass or more of the curing agent with respect to 100 parts by mass of the epoxy compound.
- the amount of the curing agent added to 100 parts by mass of the epoxy compound is, for example, 5, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70 parts by mass. may be within a range between any two of the numerical values exemplified in .
- the rubber composition according to one embodiment of the present invention can further improve the mechanical properties by containing the curing agent at the above lower limit or more, and can prevent shortening of the scorch time by making the curing agent at the above lower limit or less. can be done.
- a rubber composition according to an embodiment of the present invention may not contain a curing agent.
- the gelation time at 160° C. is preferably 60 minutes or less.
- the gelling time is, for example, 10, 15, 20, 25, 30, 35, 40, 45, 50, 55, 60 minutes, even within a range between any two of the values exemplified herein. good.
- the rubber composition according to the present invention may contain a vulcanizing agent.
- the type of vulcanizing agent is not particularly limited as long as it does not impair the effects of the present invention.
- the vulcanizing agent is preferably a vulcanizing agent that can be used for vulcanizing chloroprene rubber.
- One or more vulcanizing agents can be freely selected and used.
- Vulcanizing agents include sulfur, metal oxides, and organic peroxides.
- metal oxides include zinc oxide, magnesium oxide, lead oxide, trilead tetroxide, iron trioxide, titanium dioxide, and calcium oxide.
- the metal oxide preferably contains zinc oxide or magnesium oxide, more preferably zinc oxide.
- organic peroxides examples include dicumyl peroxide, benzoyl peroxide, 1,1-bis(t-butylperoxy)-3,5,5-trimethylcyclohexane, diisobutyryl peroxide, and cumylperoxy neodeca.
- the vulcanizing agent when the rubber contained in the rubber composition is 100 parts by mass, the vulcanizing agent is 3 to 3. It is preferable to include 15 parts by mass.
- the content of the vulcanizing agent is, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 when the rubber contained in the rubber composition is 100 parts by mass. Parts by weight, and may be in a range between any two of the numerical values exemplified herein.
- a rubber composition according to an embodiment of the present invention may contain a metal oxide and an organic peroxide.
- the amount of the organic peroxide added can be 0.3 to 1.8 parts by mass with respect to 100 parts by mass of the chloroprene rubber.
- the amount of the organic peroxide added is, for example, 0.3, 0.4, 0.5, 0.6, 0.7, 0.8, 0.9, 1.0, 1.1, 1.2. , 1.3, 1.4, 1.5, 1.6, 1.7, 1.8 parts by weight, even within a range between any two of the values exemplified herein. good.
- the rubber composition according to one embodiment of the present invention may contain hydrotalcite.
- hydrotalcite one represented by the following formula (6) can be used.
- M 2+ at least one divalent metal ion selected from Mg 2+ , Zn 2+ , etc.
- M 3+ at least one trivalent metal ion selected from Al 3+ , Fe 3+ , etc.
- a n ⁇ Co 3 2 ⁇ , Cl ⁇ , At least one n-type anion selected from NO 3 2- , etc.
- X 0 ⁇ X ⁇ 0.33.
- the amount of hydrotalcite added can be 1 to 10 parts by mass with respect to 100 parts by mass of the chloroprene rubber.
- the amount of hydrotalcite added is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 parts by mass, and is within the range between any two of the numerical values exemplified here.
- the rubber composition according to the present invention may contain a plasticizer/softener.
- the plasticizer/softener is added to adjust the processability of the unvulcanized rubber composition and the flexibility of the vulcanized product and vulcanized molding after vulcanization.
- the plasticizer/softener is not particularly limited as long as it is compatible with rubber.
- Plasticizers and softeners include vegetable oils such as rapeseed oil, linseed oil, castor oil and coconut oil, phthalate plasticizers, DUP (diundecyl phthalate), DOP (dioctyl phthalate), DINP (diisononyl phthalate), DOTP ( dioctyl terephthalate), DOS (dioctyl sebacate), DBS (dibutyl sebacate), DOA (dioctyl adipate), DINCH (diisononyl 1,2-cyclohexanedicarboxylate), TOP (trioctyl phosphate), TBP (tributyl phosphate) ester-based plasticizers such as phosphate), ether ester-based compounds, thioether-based plasticizers, aromatic oils, naphthenic oils, lubricating oils, process oils, paraffin, liquid paraffin, petroleum jelly, petroleum-based plasticizers such as petroleum asphalt
- a rubber composition according to an embodiment of the present invention can contain 5 to 50 parts by mass of a plasticizer/softener per 100 parts by mass of rubber contained in the rubber composition.
- the plasticizer/softener is, for example, 5, 10, 15, 20, 25, 30, 35, 40, 45, or 50 parts by mass, within the range between any two of the numerical values exemplified here. good too.
- the rubber composition according to the present invention can contain fillers and reinforcing materials.
- Fillers and reinforcing materials include furnace carbon black such as SAF, ISAF, HAF, EPC, XCF, FEF, GPF, HMF, SRF, modified carbon black such as hydrophilic carbon black, channel black, soot black, FT, Thermal carbon such as MT, acetylene black, ketjen black, silica, clay, talc, and calcium carbonate can be mentioned. These can be used individually by 1 type or in combination of 2 or more types. From the viewpoint of improving hardness, the rubber composition according to the present invention preferably contains silica.
- the rubber composition according to one embodiment of the present invention can contain 20 to 80 parts by mass of filler/reinforcing material or silica, and 35 to 65 parts by mass, when the rubber contained in the rubber composition is 100 parts by mass. It is preferable to include The content of the filler/reinforcing material or silica is, for example, 20, 25, 30, 35, 40, 45, 50, 55, 60, 65, 70, 75, 80 parts by mass, and the numerical values illustrated here It may be in the range between any two.
- the rubber composition according to one embodiment of the present invention further improves the hardness of the vulcanizate/vulcanized molding by containing the filler/reinforcing material, particularly the content of silica within the above numerical range. can be done.
- the rubber composition according to one embodiment of the present invention may contain a silane coupling agent.
- the silane coupling agent is not particularly limited, and those used in commercially available rubber compositions can be used. Examples include vinyl coupling agents, epoxy coupling agents, styryl coupling agents and methacrylic coupling agents. There are ring agents, acrylic coupling agents, amino coupling agents, polysulfide coupling agents, and mercapto coupling agents.
- vinyl-based coupling agents, methacrylic-based coupling agents, and acrylic-based coupling agents which initiate reactions under high-temperature conditions during crosslinking, are preferred from the viewpoint of scorch resistance and reinforcing effects.
- silane coupling agents include bis-(3-triethoxysilylpropyl) tetrasulfide, bis-(3-trimethoxinelylpropyl) tetrasulfide, and bis-(3-methyldimethoxysilylpropyl) tetrasulfide.
- the rubber composition according to one embodiment of the present invention can contain 0.5 to 10 parts by mass of a silane coupling agent when the rubber contained in the rubber composition is 100 parts by mass. , 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 parts by mass, and may be within a range between any two of the numerical values exemplified here.
- the rubber composition according to the present invention may further contain a lubricant/processing aid.
- Lubricants and processing aids are mainly added to improve processability, such as making it easier for the rubber composition to separate from rolls, molding dies, extruder screws, and the like.
- lubricants and processing aids include fatty acids such as stearic acid, paraffin-based processing aids such as polyethylene, fatty acid amides, vaseline, and factice. These can be used individually by 1 type or in combination of 2 or more types.
- the rubber composition according to the present invention can contain 1 to 15 parts by mass of a lubricant/processing aid when the rubber contained in the rubber composition is 100 parts by mass, and can also be 1 to 10 parts by mass.
- the content of the lubricant/processing aid is, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15 parts by mass. It may be in a range between any two of the numbers.
- the rubber composition according to the present invention can contain a vulcanization accelerator. 5.0 parts by mass can be included.
- the content of the vulcanization accelerator is, for example, 0.3, 0.5, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0, 4.5 , 5.0 parts by mass, and may be within a range between any two of the numerical values exemplified herein.
- the rubber composition according to the present invention may also contain no vulcanization accelerator.
- the type of vulcanization accelerator is not particularly limited as long as it does not impair the effects of the present invention.
- the vulcanization accelerator is preferably a vulcanization accelerator that can be used for vulcanization of chloroprene rubber.
- One or more vulcanization accelerators can be freely selected and used. Examples of vulcanization accelerators include thiuram-based, dithiocarbamate-based, thiourea-based, guanidine-based, xanthate-based, and thiazole-based accelerators.
- Thiuram-based vulcanization accelerators include tetramethylthiuram disulfide (TMTD), tetraethylthiuram disulfide, tetrabutylthiuram disulfide, tetrakis(2-ethylhexyl)thiuram disulfide, tetramethylthiuram monosulfide, and dipentamethylenethiuram tetrasulfide. mentioned.
- Dithiocarbamate-based vulcanization accelerators include sodium dibutyldithiocarbamate, zinc dimethyldithiocarbamate, zinc diethyldithiocarbamate, zinc N-ethyl-N-phenyldithiocarbamate, zinc N-pentamethylenedithiocarbamate, and copper dimethyldithiocarbamate. , ferric dimethyldithiocarbamate, tellurium diethyldithiocarbamate, and the like.
- Thiourea-based vulcanization accelerators include ethylenethiourea, diethylthiourea (N,N'-diethylthiourea), trimethylthiourea, diphenylthiourea (N,N'-diphenylthiourea), 1,3-trimethylene-2-thiourea, and the like. and thiourea compounds.
- Guanidine-based vulcanization accelerators include 1,3-diphenylguanidine, 1,3-di-o-tolylguanidine, 1-o-tolylbiguanide, and dicatechol borate di-o-tolylguanidine salts. .
- xanthate-based vulcanization accelerators include zinc butylxanthate and zinc isopropylxanthate.
- Thiazole-based vulcanization accelerators include 2-mercaptobenzothiazole, di-2-benzothiazolyl disulfide, 2-mercaptobenzothiazole zinc salt, cyclohexylamine salt of 2-mercaptobenzothiazole, 2-(4'- morpholinodithio)benzothiazole, N-cyclohexylbenzothiazole-2-sulfenamide and the like. These can be used individually by 1 type or in combination of 2 or more types.
- the rubber composition according to the present invention may further contain components such as an anti-aging agent, an antioxidant, and a flame retardant within a range that does not impair the effects of the present invention.
- Anti-aging agents and antioxidants include ozone anti-aging agents, phenolic anti-aging agents, amine anti-aging agents, acrylate anti-aging agents, imidazole anti-aging agents, metal carbamates, waxes, and phosphorus anti-aging agents. agents, sulfur-based antioxidants, and the like.
- Examples of imidazole antioxidants include 2-mercaptobenzimidazole, 2-mercaptomethylbenzimidazole and zinc salts of 2-mercaptobenzimidazole.
- the rubber composition according to the present invention can contain 0.1 to 10 parts by mass of an anti-aging agent/antioxidant per 100 parts by mass of the rubber contained in the rubber composition.
- a rubber composition according to one embodiment of the present invention is obtained by kneading a chloroprene-based rubber, an epoxy-based compound, and other necessary components at a temperature not higher than the vulcanization temperature.
- a device for kneading the raw material components conventionally known kneading devices such as a mixer, a Banbury mixer, a kneader mixer, and an open roll can be used.
- the rubber composition according to one embodiment of the present invention preferably has a scorch time of 7 minutes or more as measured by the Mooney scorch test at 125° C. in accordance with JIS K 6300-1. minutes or more, and even more preferably 11 minutes or more. Scorch times are, for example, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 minutes and ranges between any two of the values exemplified here. may be within
- the vulcanizate obtained by molding according to JIS K6299 preferably has a type A durometer hardness measured according to JIS K6253 of 80 or more, preferably 85 or more. is more preferable, and 90 or more is even more preferable.
- Type A durometer hardness is, for example, 80, 85, 90, 95, 100, and may range between any two of the values exemplified herein.
- the tensile strength of the vulcanizate obtained by molding according to JIS K6299, measured according to JIS K 6251 is preferably 21 MPa or more, and preferably 23 MPa or more. is more preferable, and 25 MPa or more is even more preferable.
- the tensile strength is, for example, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30 MPa, and may be within a range between any two of the values exemplified here.
- the rubber composition according to one embodiment of the present invention has a vulcanizate T10 of less than -10°C obtained by vulcanizing the rubber composition according to JIS K6299, determined by Gehman torsion test based on JIS K 6261. is preferred, less than -20°C is more preferred, and less than -30°C is even more preferred.
- T10 is, for example, ⁇ 40, ⁇ 35, ⁇ 30, ⁇ 25, ⁇ 20, ⁇ 15, ⁇ 10° C., and may be in the range between any two of the values exemplified herein.
- the unvulcanized molded article according to the present embodiment uses the rubber composition according to the present embodiment. It is a molded product (molded product) in a sulfuric state).
- the method for producing an unvulcanized molded article according to this embodiment includes a step of molding the rubber composition (unvulcanized state) according to this embodiment.
- the unvulcanized molded article according to this embodiment is made of the rubber composition (unvulcanized state) according to this embodiment.
- the vulcanizate according to this embodiment is a vulcanizate of the rubber composition according to this embodiment.
- a method for producing a vulcanizate according to the present embodiment includes a step of vulcanizing the rubber composition according to the present embodiment.
- the vulcanized molded article according to this embodiment is a vulcanized molded article of the rubber composition according to this embodiment.
- the vulcanized molded article according to the present embodiment uses the vulcanized material according to the present embodiment, and is a molded article (molded article) of the vulcanized material according to the present embodiment.
- the vulcanized molding according to this embodiment is made of the vulcanizate according to this embodiment.
- the vulcanized molded article according to the present embodiment can be obtained by molding a vulcanized product obtained by vulcanizing the rubber composition (unvulcanized state) according to the present embodiment. It can also be obtained by vulcanizing the molded article obtained by molding the rubber composition (unvulcanized state) according to.
- the vulcanized molded article according to this embodiment can be obtained by vulcanizing the rubber composition according to this embodiment after or during molding.
- a method for manufacturing a vulcanized molded article according to the present embodiment includes a step of molding a vulcanized article according to the present embodiment or a step of vulcanizing an unvulcanized molded article according to the present embodiment.
- the unvulcanized molded article, vulcanized article and vulcanized molded article according to the present embodiment can be used as rubber parts in various industrial fields such as buildings, constructions, ships, railroads, coal mines and automobiles. Since the rubber composition according to the present invention has a sufficiently long scorch time of the unvulcanized product, it is excellent in workability, and the vulcanized product has hardness, tensile strength, and cold resistance in a well-balanced manner. It can be used as various members to be used.
- the rubber composition according to one embodiment of the present invention can be used as rubber parts in various industrial fields such as buildings, structures, ships, railroads, coal mines, automobiles, etc. , hose materials, rubber molds, gaskets, rubber rolls, industrial cables, industrial conveyor belts, sponges and other rubber parts.
- the rubber composition according to one embodiment of the present invention can be suitably used as a rubber roll from the viewpoint of having particularly high hardness.
- Automotive rubber members include gaskets, oil seals, packing, and the like, and are parts that prevent the leakage of liquids and gases, and the intrusion of dirt and foreign matter such as rainwater and dust in machinery and equipment.
- gaskets used for stationary applications, and oil seals and packings used for moving parts.
- various materials are used depending on the purpose, as opposed to soft gaskets such as O-rings and rubber sheets.
- Packings are also used for shafts of pumps and motors, rotating parts such as the movable parts of valves, reciprocating parts such as pistons, connecting parts of couplers, water shut-off parts of faucets, and the like.
- the rubber composition of the present invention can increase the tensile strength and hardness of these members. This makes it possible to produce seals for use in high load applications, which are difficult with conventional rubber compositions.
- the hose material is a bendable tube, and specifically includes high/low pressure hoses for water, oil, air, steam, and hydraulic pressure.
- the rubber composition of the present invention can increase the tensile strength of hose materials. As a result, it is possible to manufacture a hose material for use in high-load applications, which has been difficult with conventional rubber compositions.
- Rubber molds include anti-vibration rubber, damping materials, and boots.
- Anti-vibration rubber and damping material are rubbers that prevent transmission of vibration. Damper, engine mount, muffler hanger, etc.
- the rubber composition of the present invention can increase the tensile strength of vibration-isolating rubbers and vibration-damping materials. As a result, it is possible to produce vibration-isolating rubbers and vibration-damping materials that can be used even in applications where high load is applied, which has been difficult with conventional rubber compositions.
- the boot is a bellows-shaped member whose outer diameter gradually increases from one end to the other end. There are boots for ball joint covers (dust cover boots) and boots for rack and pinion gears.
- the rubber composition of the present invention can increase the tensile strength of boots. This makes it possible to produce boots for use in applications with higher loads than conventional rubber compositions.
- Gaskets, oil seals, and packings are parts used in machinery and equipment to prevent leaks of liquids and gases, rainwater, dust, and other dirt and foreign matter from entering the interior. Specifically, they are used for fixed purposes. There are gaskets and oil seals and packings used for moving parts and movable parts. For gaskets whose sealing portions are fixed with bolts or the like, various materials are used depending on the purpose, as opposed to soft gaskets such as O-rings and rubber sheets. Packings are also used for shafts of pumps and motors, rotating parts such as the movable parts of valves, reciprocating parts such as pistons, connecting parts of couplers, water shut-off parts of faucets, and the like.
- the rubber composition of the present invention can increase the tensile strength and hardness of these members. This makes it possible to produce seals that can be used even in high-load applications that have been difficult with conventional rubber compositions.
- a rubber roll is manufactured by adhesively coating a metal core such as an iron core with rubber, and is generally manufactured by spirally winding a rubber sheet around a metal iron core.
- rubber materials such as NBR, EPDM, CR, etc. are used according to the required characteristics of various applications such as paper manufacturing, various metal manufacturing, film manufacturing, printing, general industrial use, agricultural equipment such as hulling, and food processing. used. Since CR has good mechanical strength to withstand the friction of objects to be conveyed, it is used for a wide range of rubber roll applications.
- rubber rolls used in environments where oil adheres, such as when manufacturing industrial materials and products for iron and paper have insufficient oil resistance and are in need of improvement.
- the rubber composition of the present invention can increase the tensile strength and hardness of rubber rolls. As a result, it is possible to manufacture a rubber roll that can be used under high tension, which has been difficult with conventional rubber compositions.
- Industrial cables are linear members for transmitting electrical and optical signals.
- a good conductor such as copper or copper alloy or an optical fiber is coated with an insulating coating layer, and a wide variety of industrial cables are manufactured depending on the structure and installation location.
- the rubber composition of the present invention can increase the tensile strength of industrial cables. As a result, it is possible to manufacture an industrial cable that can be used even in applications where a high load is applied, which has been difficult with conventional rubber compositions.
- Industrial conveyor belts come in rubber, resin, and metal belts, and are selected according to a wide variety of usage methods. Among these, rubber conveyor belts are inexpensive and widely used.
- the rubber composition of the present invention can increase the tensile strength of industrial conveyor belts. As a result, it is possible to manufacture industrial conveyor belts that are used under high loads, which has been difficult with conventional rubber compositions.
- (sponge) Sponge is a porous material with a myriad of fine holes inside, and is specifically used for vibration-proof members, sponge seal parts, wet suits, shoes, and the like.
- the rubber composition of the present invention can increase the tensile strength of sponge.
- chloroprene-based rubber is used, it is also possible to enhance the flame retardancy of the sponge.
- the hardness of the resulting sponge can be adjusted as appropriate by adjusting the content of the foaming agent.
- Methods for molding the rubber composition (unvulcanized state) and the vulcanized product according to the present embodiment include press molding, extrusion molding, calendar molding, and the like.
- the temperature for vulcanizing the rubber composition may be appropriately set according to the composition of the rubber composition, and may be 140 to 220°C or 160 to 190°C.
- the vulcanization time for vulcanizing the rubber composition may be appropriately set depending on the composition of the rubber composition, the shape of the unvulcanized molding, etc., and may be 10 to 60 minutes.
- emulsion polymerization was carried out at a polymerization temperature of 40° C. under a nitrogen stream.
- the above-mentioned chloroprene is added in portions from 20 seconds after the start of polymerization, the amount of added portions is adjusted with a solenoid valve based on the change in the heat quantity of the refrigerant for 10 seconds from the start of polymerization, and the flow rate is readjusted every 10 seconds thereafter. continuously.
- the above-mentioned polymerization rate [%] of the chloroprene-based latex was calculated from the dry mass when the chloroprene-based latex was air-dried. Specifically, it was calculated from the following formula (A).
- the "solid content concentration” is the solid content concentration [% by mass] after heating 2 g of the sampled chloroprene-based latex at 130 ° C. and excluding volatile components such as solvent (water), volatile chemicals, and raw materials. is.
- the "total charged amount” is the total amount [g] of raw materials, reagents and solvent (water) charged into the polymerization vessel from the start of polymerization to a certain time.
- the “evaporation residue” is the mass [g] of chemicals remaining as solid content together with the polymer without being volatilized under conditions of 130°C among the chemicals and raw materials charged up to a certain time from the start of polymerization.
- the “amount of monomer charged” is the total amount [g] of the amount of the monomer initially charged in the polymerization vessel and the amount of the monomer gradually added from the start of the polymerization to a certain time.
- the “monomer” here is the total amount of chloroprene and acrylonitrile.
- Polymerization rate ⁇ [(total charged amount x solid content concentration/100) - evaporation residue]/ charged amount of monomer ⁇ x 100 (A)
- the chloroprene-based latex A-2 After adjusting the pH of the above-mentioned chloroprene-based latex A-2 to 7.0 using acetic acid or sodium hydroxide, the chloroprene-based latex is freeze-coagulated on a metal plate cooled to -20 ° C. to demulsify. A sheet was thus obtained. After washing this sheet with water, it was dried at 130° C. for 15 minutes to obtain a solid chloroprene rubber A-2.
- the weight average molecular weight (Mw) of the chloroprene rubber is 473 ⁇ 10 3 g/mol, the number average molecular weight (Mn) is 138 ⁇ 10 3 g/mol, and the molecular weight distribution (Mw/Mn) is 3.4. there were.
- the content of acrylonitrile monomer units contained in the chloroprene rubber A-2 was calculated from the content of nitrogen atoms in the chloroprene-acrylonitrile copolymer rubber. Specifically, using an elemental analyzer (Sumigraph 220F: manufactured by Sumika Chemical Analysis Service, Ltd.), the content of nitrogen atoms in 100 mg of chloroprene-based rubber A-2 was measured, and the monomer unit of acrylonitrile was measured. The content was calculated. The content of acrylonitrile monomer units was 10.0% by mass.
- the elemental analysis described above was performed as follows.
- the electric furnace temperature was set to 900°C for the reactor, 600°C for the reduction furnace, 70°C for the column temperature, and 100°C for the detector temperature. flowed.
- a calibration curve was prepared using aspartic acid (10.52%) with a known nitrogen content as a standard substance.
- the acrylonitrile monomer unit content of the chloroprene rubber A-2 obtained by the above production method was 10.0% by weight.
- Chloroprene rubber - The above-mentioned chloroprene-based rubber A-1 (chloroprene-acrylonitrile copolymer AN (acrylonitrile monomer unit) content of 5% by mass), ⁇ Chloroprene-based rubber A-2 (chloroprene-acrylonitrile copolymer, AN content of 10% by mass), ⁇ Chloroprene-based rubber A-3 (chloroprene-acrylonitrile copolymer, AN content of 20% by mass), ⁇ Chloroprene-based rubber A-4 (chloroprene-acrylonitrile copolymer, AN content of 25% by mass), ⁇ Chloroprene rubber A-5 (Mercaptan-modified chloroprene rubber (chloroprene homopolymer), “S-40V” manufactured by Denka Co., Ltd.) Reactive plasticizer: Epoxy compound A (molecular weight 700),
- ⁇ Preparation of vulcanized molded body> The obtained rubber composition was press-vulcanized under conditions of 160° C. for 40 minutes according to JIS K6299 to prepare a vulcanized sheet-like body having a thickness of 2 mm.
- Durometer hardness (type A durometer) Durometer hardness (type A) defined in JIS K 6253 was measured for the sheet-like vulcanized molded body using an Asker rubber hardness tester type A (Kobunshi Keiki Co., Ltd.). The obtained hardness was evaluated according to the following criteria (details of durometer hardness measurement are JIS K 6253-3). A: 90 or more B: 85 or more and less than 90 C: 80 or more and less than 85 D: less than 80
- T10 The temperature (T10) at which the 180° torsional modulus of the above-described vulcanized molded body becomes ten times the 180° torsional modulus at room temperature was determined.
- the obtained T10 was evaluated according to the following criteria. A: Less than -30°C B: -30°C or more and less than -20°C C: -20°C or more and less than -10°C D: -10°C or more
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Abstract
Description
また、本発明の別の観点によれば、上記記載の加硫物を用いた加硫成形体が提供される。
[1]不飽和ニトリル単量体単位の含有率が25質量%未満であるクロロプレン系ゴム、及び重量平均分子量が100を超え900未満のエポキシ系化合物を含むゴム組成物であって、前記クロロプレン系ゴム100質量部に対して、前記エポキシ系化合物を0.1~25質量部含有するゴム組成物。
[2]前記不飽和ニトリル単量体がアクリロニトリルである、[1]に記載のゴム組成物。
[3]前記エポキシ系化合物が、脂環式エポキシ化合物、エピクロロヒドリンとビスフェノールとの共重合体からなるエポキシ樹脂、及び、エポキシ化不飽和脂肪酸エステルから選ばれる少なくとも1種のエポキシ系化合物である、[1]または[2]に記載のゴム組成物。
[4]前記クロロプレン系ゴム100質量部に対して、充填材を20~80質量部含有する、[1]~[3]のいずれか一項に記載のゴム組成物。
[5]前記エポキシ系化合物100質量部に対して、硬化剤を5質量部以上含有する、[1]~[4]のいずれか一項に記載のゴム組成物。
[6]前記ゴム組成物を、JISK6299に基づき成形して得た加硫物の、JISK6253に基づき測定したタイプAデュロメータ硬度が80以上である、[1]~[5]のいずれか一項に記載のゴム組成物。
[7][1]~[6]のいずれか一項に記載のゴム組成物の加硫物。
[8][7]に記載の加硫物を用いた加硫成形体。
本発明に係るゴム組成物は、不飽和ニトリル単量体単位の含有率が25質量%未満であるクロロプレン系ゴム、及び重量平均分子量が100を超え900未満のエポキシ系化合物を含み、クロロプレン系ゴム100質量部に対して、前記エポキシ系化合物を0.1~25質量部含有する。
本発明によれば、特定の種類のクロロプレン系ゴムと、特定の分子量を有するエポキシ系化合物を含み、かつエポキシ系化合物の配合量を特定することで、未加硫物のスコーチタイム、並びに、加硫物の硬度、引張強度、及び耐寒性をバランス良く向上させることができる。
本発明に係るクロロプレン系ゴムは、クロロプレン(2-クロロ-1,3-ブタジエン)を単量体単位(クロロプレンの単量体単位。単量体単位=構造単位)として有するクロロプレン系重合体を含むゴムを示す。クロロプレン系重合体としては、クロロプレンの単独重合体、クロロプレンの共重合体(クロロプレンと、クロロプレンに共重合可能な単量体との共重合体)等が挙げられる。クロロプレン系重合体のポリマー構造は、特に限定されるものではない。
本発明の一実施形態に係るクロロプレン系ゴムは、ゴムを100質量%としたとき、不飽和ニトリル単量体単位の含有率が25質量%未満であり、不飽和ニトリル単量体単位の含有率が1質量%以上、25質量%未満であることが好ましい。
本発明の一実施形態に係るクロロプレン系ゴムにおける不飽和ニトリル単量体単位の含有率は、例えば、0、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16、17、18、19、20、21、22、23、24質量%、25質量%未満であり、ここで例示した数値の何れか2つの間の範囲内であってもよい。不飽和ニトリル単量体単位の含有率を25質量%未満とすることにより、得られるゴム組成物は十分な耐寒性を有するものとなる。また、特には、不飽和ニトリル単量体単位の含有率を1質量%以上とすることにより、得られるゴム組成物は十分な耐油性を有するものとなり、かつ、硬度、引張強度、及び耐寒性のバランスに優れる加硫成形体を得ることができる。
また、本発明の一実施形態に係るクロロプレン系ゴムは、クロロプレン単量体単位及び不飽和ニトリル単量体単位のみからなるものとすることもでき、クロロプレン単量体単位のみからなるものとすることもできる。
本発明の一実施形態に係るゴム組成物が、2種以上のクロロプレン系ゴムを含む場合、ゴム組成物に含まれる2種以上のクロロプレン系ゴムに含まれる不飽和ニトリル単量体単位の含有率が25質量%未満であることが好ましい。
本発明に係るクロロプレン系ゴムの製造方法は特に限定されないが、クロロプレン単量体を含む原料単量体を乳化重合する乳化重合工程を含む製造方法によって得ることができる。
本発明の一実施形態に係る乳化重合工程では、クロロプレン単量体、又は、クロロプレン単量体及び不飽和ニトリル単量体を含む単量体を、乳化剤や分散剤や触媒や連鎖移動剤等を適宜に用いて乳化重合させ、目的とする最終転化率に達した際に重合停止剤を添加してクロロプレン単量体単位を含むクロロプレン系重合体を含むラテックスを得ることができる。
次に、乳化重合工程により得られた重合液から、未反応単量体の除去を行うことができる。その方法は、特に限定されるものではなく、例えば、スチームストリッピング法が挙げられる。
その後、pHを調整し、常法の凍結凝固、水洗、熱風乾燥などの工程を経て、クロロプレン系重合体を含むクロロプレン系ゴムを得ることができる。
本発明に係るゴム組成物は、エポキシ系化合物、すなわち、エポキシ基を有する化合物を含む。エポキシ系化合物は、未加硫物における流動性を向上させ、また、加硫時に硬化することにより、加硫物における硬度や引張強度等の機械的特性を向上させる、反応型可塑剤(硬化型可塑剤)としての機能を有することができる。
エポキシ系化合物としては、脂環式エポキシ化合物、エピクロロヒドリンとビスフェノールとの共重合体からなるエポキシ樹脂、エポキシ化不飽和脂肪酸エステル、エポキシ基を有するジエン系重合体(クロロプレン系重合体に該当する化合物を除く)を挙げることができる。エポキシ系化合物は、脂環式エポキシ化合物、エピクロロヒドリンとビスフェノールとの共重合体からなるエポキシ樹脂、及び、エポキシ化不飽和脂肪酸エステルからなる群から選択される1種以上を含むことが好ましい。
エポキシ基を有するジエン系重合体としては、エポキシ基を有する、ポリブタジエン、ポリイソプレン等の脂肪族共役ジエン重合体;スチレン-ブタジエン重合体(SBR)等の芳香族ビニル・脂肪族共役ジエン共重合体;アクリロニトリル-ブタジエン重合体(NBR)等のシアン化ビニル-共役ジエン共重合体;水素化SBR;水素化NBRなどが挙げられる。エポキシ基を有するジエン系重合体は、例えば、下記式(5)で表される化合物を含み得る。
本発明に係るエポキシ系化合物の重量平均分子量は、例えば、100超、110、150、200、250、300、350、400、450、500、550、600、650、700、750、800、850、890、900未満であり、ここで例示した数値の何れか2つの間の範囲内であってもよい。
エポキシ系化合物の分子量を上記上限以下とすることにより、未加硫物のスコーチタイムを向上することができる。また、エポキシ系化合物の分子量を上記下限以下とすることにより、加硫物の硬度、引張強度、及び耐寒性をバランス良く向上させることができる。
重量平均分子量は、ゲルパーミエーションクロマトグラフィー(GPC)で測定し、ポリスチレン換算することで得ることが可能であり、クロロプレン重合体の重量平均分子量と同様の方法により測定できる。
エポキシ系化合物の含有率を上記数値範囲内とすることによって、未加硫物のスコーチタイム、並びに、加硫物の硬度、引張強度、及び耐寒性をバランス良く向上させることができるゴム組成物となる。
本発明の一実施形態に係るゴム組成物は、硬化剤を含むことができる。硬化剤としては、エポキシ系化合物の硬化に寄与するものであれば特に制限はない。硬化剤としては、カルボン酸ヒドラジド系硬化剤、アミン系硬化剤、フェノール系硬化剤、酸無水物系硬化剤、を挙げることができる。これらは、1種単独で又は2種以上を組み合わせて用いることができる。
ゲル化時間が上記数値範囲内である硬化剤を選択することにより、十分に長い未加硫物のスコーチタイム、及び、加硫物の優れた機械的特性の両立を図ることができる。
本発明に係るゴム組成物は、加硫剤を含むことができる。
加硫剤の種類は、本発明の効果を損なわなければ特に限定されない。加硫剤は、クロロプレン系ゴムの加硫に用いることができる加硫剤であることが好ましい。加硫剤は、1種又は2種以上自由に選択して用いることができる。
加硫剤としては、硫黄、金属酸化物、有機過酸化物を挙げることができる。
本発明の一実施形態に係るゴム組成物はハイドロタルサイトを含むことができる。
ハイドロタルサイトとしては、下記式(6)で表されるものを用いることができる。
[M2+ 1-xM3+ x(OH)2]x+[An-x/n・mH2O]x- (6)
M2+:Mg2+、Zn2+などから選ばれる少なくとも一つの2価金属イオン
M3+:Al3+、Fe3+などから選ばれる少なくとも一つの3価金属イオン
An-:Co3 2-、Cl―、NO3 2-などから選ばれる少なくとも一つのn型アニオン
X:0<X≦0.33とすることができる。
本発明に係るゴム組成物は、可塑剤・軟化剤を含むことができる。可塑剤・軟化剤は、未加硫ゴム組成物の加工性並びに加硫後の加硫物及び加硫成形体の柔軟性を調整するために添加される。可塑剤・軟化剤は、ゴムと相溶性のある可塑剤・軟化剤であれば特に制限はない。可塑剤・軟化剤としては、菜種油、アマニ油、ヒマシ油、ヤシ油などの植物油、フタレート系可塑剤、DUP(フタル酸ジウンデシル)、DOP(フタル酸ジオクチル)、DINP(フタル酸ジイソノニル)、DOTP(テレフタル酸ジオクチル)、DOS(セバシン酸ジオクチル)、DBS(セバシン酸ジブチル)、DOA(アジピン酸ジオクチル)、DINCH(1,2-シクロヘキサンジカルボン酸ジイソノニル)、TOP(トリオクチルフォスフェート)、TBP(トリブチルフォスフェート)等のエステル系可塑剤、エーテルエステル系化合物、チオエーテル系可塑剤、アロマ系オイル、ナフテン系オイル、潤滑油、プロセスオイル、パラフィン、流動パラフィン、ワセリン、石油アスファルトなどの石油系可塑剤などがある。これらは、1種単独で又は2種以上を組み合わせて用いることができる。
本発明に係るゴム組成物は、充填材・補強材を含むことができる。
充填材・補強材としては、SAF、ISAF、HAF、EPC、XCF、FEF、GPF、HMF、SRFなどのファーネスカーボンブラック、親水性カーボンブラックなどの改質カーボンブラック、チャンネルブラック、油煙ブラック、FT、MTなどのサーマルカーボン、アセチレンブラック、ケッチェンブラック、シリカ、クレー、タルク、炭酸カルシウムを挙げることができる。これらは、1種単独で又は2種以上を組み合わせて用いることができる。本発明に係るゴム組成物は、硬度を向上させる観点から、シリカを含むことが好ましい。
本発明の一実施形態に係るゴム組成物は、充填材・補強材、特にはシリカの含有率を上記数値範囲内含有することにより、さらに加硫物・加硫成形体の硬度を向上させることができる。
本発明の一実施形態に係るゴム組成物は、シランカップリング剤を含むことができる。
シランカップリング剤としては、特に制限はなく、市販のゴム組成物に使用されているものが使用でき、例えば、ビニル系カップリング剤、エポキシ系カップリング剤、スチリル系カップリング剤、メタクリル系カップリング剤、アクリル系カップリング剤、アミノ系カップリング剤、ポリスルフィド系カップリング剤、メルカプト系カップリング剤がある。特に、耐スコーチ性や補強効果の観点から架橋時の高温条件下で反応が開始されるビニル系カップリング剤、メタクリル系カップリング剤、アクリル系カップリング剤が好ましい。
上記のシランカップリング剤を含み、また、シランカップリング剤の含有率を上記数値範囲内とすることにより、ゴム中へのシリカフィラーの分散性やゴム及びエポキシ系化合物とシリカフィラー間の補強効果を向上させ、かつ、スコーチの発生を抑制することができる。
本発明に係るゴム組成物は、さらに滑剤・加工助剤を含むこともできる。滑剤・加工助剤は、主に、ゴム組成物がロールや成形金型、押出機のスクリューなどから剥離しやすくなるようにするなど、加工性を向上させるために添加する。滑剤・加工助剤としては、ステアリン酸等の脂肪酸、ポリエチレン等のパラフィン系加工助剤、脂肪酸アミド、ワセリン、ファクチス等が挙げられる。これらは、1種単独で又は2種以上を組み合わせて用いることができる。本発明に係るゴム組成物は、ゴム組成物に含まれるゴムを100質量部としたとき、滑剤・加工助剤を1~15質量部含むことができ、1~10質量部とすることもできる。滑剤・加工助剤の含有量は、例えば、1、2、3、4、5、6、7、8、9、10、11、12、13、14、15質量部であり、ここで例示した数値の何れか2つの間の範囲内であってもよい。
本発明に係るゴム組成物は、加硫促進剤を含むことができ、ゴム組成物に含まれるゴムを100質量部としたとき、加硫促進剤を0.3~5.0質量部含むことができる。加硫促進剤の含有量は、例えば、0.3、0.5、1.0、1.5、2.0、2.5、3.0、3.5、4.0、4.5、5.0質量部であり、ここで例示した数値の何れか2つの間の範囲内であってもよい。なお、本発明に係るゴム組成物は、加硫促進剤を含まないものとすることもできる。
加硫促進剤としては、チウラム系、ジチオカルバミン酸塩系、チオウレア系、グアニジン系、キサントゲン酸塩系、チアゾール系等が挙げられる。
ジチオカルバミン酸塩系の加硫促進剤としては、ジブチルジチオカルバミン酸ナトリウム、ジメチルジチオカルバミン酸亜鉛、ジエチルジチオカルバミン酸亜鉛、N-エチル-N-フェニルジチオカルバミン酸亜鉛、N-ペンタメチレンジチオカルバミン酸亜鉛、ジメチルジチオカルバミン酸銅、ジメチルジチオカルバミン酸第二鉄、ジエチルジチオカルバミン酸テルル等が挙げられる。
チオウレア系の加硫促進剤としては、エチレンチオウレア、ジエチルチオウレア(N,N'-ジエチルチオウレア)、トリメチルチオウレア、ジフェニルチオウレア(N,N'-ジフェニルチオウレア)、1、3-トリメチレン-2-チオウレア等のチオウレア化合物が挙げられる。
グアニジン系の加硫促進剤としては、1,3-ジフェニルグアニジン、1,3-ジ-o-トリルグアニジン、1-o-トリルビグアニド、ジカテコールボレートのジ-o-トリルグアニジン塩等が挙げられる。
キサントゲン酸塩系の加硫促進剤としては、ブチルキサントゲン酸亜鉛、イソプロピルキサントゲン酸亜鉛等が挙げられる。
チアゾール系の加硫促進剤としては、2-メルカプトベンゾチアゾール、ジ-2-ベンゾチアゾリルジスルフィド、2-メルカプトベンゾチアゾール亜鉛塩、2-メルカプトベンゾチアゾールのシクロヘキシルアミン塩、2-(4'-モルホリノジチオ)ベンゾチアゾール、N-シクロヘキシルベンゾチアゾール-2-スルフェンアミド等が挙げられる。
これらは、1種単独で又は2種以上を組み合わせて用いることができる。
本発明に係るゴム組成物は、上記した成分に加え、老化防止剤、酸化防止剤、難燃剤等の成分を、本発明の効果を阻害しない範囲でさらに含むことができる。
老化防止剤・酸化防止剤としては、オゾン老化防止剤、フェノール系老化防止剤、アミン系老化防止剤、アクリレート系老化防止剤、イミダゾール系老化防止剤、カルバミン酸金属塩、ワックス、リン系老化防止剤、硫黄系老化防止剤などを挙げることができる。イミダゾール系老化防止剤としては、2-メルカプトベンゾイミダゾール、2-メルカプトメチルベンゾイミダゾール及び2-メルカプトベンゾイミダゾールの亜鉛塩を挙げることができる。
本発明に係るゴム組成物は、ゴム組成物に含まれるゴムを100質量部としたとき、老化防止剤・酸化防止剤を0.1~10質量部含むことができる。
本発明の一実施形態に係るゴム組成物は、クロロプレン系ゴム、エポキシ系化合物、及び必要とされるその他の成分を加硫温度以下の温度で混練することで得られる。原料成分を混練する装置としては、従来公知のミキサー、バンバリーミキサー、ニーダーミキサー、オープンロールなどの混練装置を挙げることができる。
本発明の一実施形態に係るゴム組成物は、JIS K 6300-1に基づき、125℃でムーニースコーチ試験により測定されるスコーチタイムが、7分以上であることが好ましく、9分以上であることがより好ましく、11分以上であることが更により好ましい。
スコーチタイムは、例えば、7、8、9、10、11、12、13、14、15、16、17、18、19、20分であり、ここで例示した数値の何れか2つの間の範囲内であってもよい。
本実施形態に係る未加硫成形体は、本実施形態に係るゴム組成物を用いており、本実施形態に係るゴム組成物(未加硫状態)の成形体(成形品)である。本実施形態に係る未加硫成形体の製造方法は、本実施形態に係るゴム組成物(未加硫状態)を成形する工程を備える。本実施形態に係る未加硫成形体は、本実施形態に係るゴム組成物(未加硫状態)からなる。
自動車用ゴム部材は、ガスケット、オイルシール及びパッキンなどがあり、機械や装置において、液体や気体の漏れや雨水や埃などのごみや異物が内部に侵入するのを防ぐ部品である。具体的には、固定用途に使われるガスケットと、運動部分・可動部分に使用されるオイルシール及びパッキンがある。シール部分がボルトなどで固定されているガスケットでは、Oリングやゴムシートなどのソフトガスケットに対して、目的に応じた各種材料が使用されている。また、パッキンは、ポンプやモーターの軸、バルブの可動部のような回転部分、ピストンのような往復運動部分、カプラーの接続部、水道蛇口の止水部などに使われる。本発明のゴム組成物は、これら部材の引張強度や硬度を高めることができる。これにより、従来のゴム組成物では困難であった高負荷がかかる用途で使用されるシールを製造することが可能である。
ホース材は、屈曲可能な管であり、具体的には、送水用、送油用、送気用、蒸気用、油圧用高・低圧ホースなどがある。本発明のゴム組成物は、ホース材の引張強度を高めることが可能である。これにより、従来のゴム組成物では困難であった高負荷がかかる用途で使用されるホース材を製造することができる。
ゴム型物は、防振ゴム、制振材、ブーツなどがある。防振ゴム及び制振材は、振動の伝達波及を防止するゴムのことであり、具体的には、自動車や各種車両用のエンジン駆動時の振動を吸収して騒音を防止するためのトーショナルダンパー、エンジンマウント、マフラーハンガーなどがある。本発明のゴム組成物は、防振ゴム及び制振材の引張強度を高めることが可能である。これにより、従来のゴム組成物では困難であった高負荷がかかる用途でも使用できる防振ゴム及び制振材を製造することができる。
また、ブーツは、一端から他端に向けて外径が次第に大きくなる蛇腹状をなす部材であり、具体的には、自動車駆動系などの駆動部を保護するための等速ジョイントカバー用ブーツ、ボールジョイントカバー用ブーツ(ダストカバーブーツ)、ラックアンドピニオンギア用ブーツなどがある。本発明のゴム組成物は、ブーツの引張強度を高めることが可能である。これにより、従来のゴム組成物よりも高負荷がかかる用途で使用されるブーツを製造することが可能である。
ガスケットや、オイルシール及びパッキンは、機械や装置において、液体や気体の漏れや雨水や埃などのごみや異物が内部に侵入するのを防ぐ部品であり、具体的には、固定用途に使われるガスケットと、運動部分・可動部分に使用されるオイルシール及びパッキンがある。シール部分がボルトなどで固定されているガスケットでは、Oリングやゴムシートなどのソフトガスケットに対して、目的に応じた各種材料が使用されている。また、パッキンは、ポンプやモーターの軸、バルブの可動部のような回転部分、ピストンのような往復運動部分、カプラーの接続部、水道蛇口の止水部などに使われる。本発明のゴム組成物は、これら部材の引張強度や硬度を高めることができる。これにより、従来のゴム組成物では困難であった高負荷がかかる用途でも使用できるシールを製造することが可能である。
ゴムロールは、鉄芯などの金属製の芯をゴムで接着被覆することによって製造されるものであり、一般に金属鉄芯にゴムシートを渦巻き状に巻き付けて製造される。ゴムロールには、製紙、各種金属製造、フィルム製造、印刷、一般産業用、籾摺りなどの農機具用、食品加工用などの種々の用途の要求特性に応じて、NBRやEPDM、CRなどのゴム材料が用いられている。CRは搬送する物体の摩擦に耐え得る良好な機械的強度を有していることから、幅広いゴムロール用途に使用されている。一方で、製鉄用、製紙用の工業用材料や製品の製造時など、油が付着する環境下で用いられるゴムロールには耐油性が不十分であり、改良が求められている。また、金、銀、ニッケル、クロム及び亜鉛など、製品にメッキ処理を施す際に酸やアルカリに晒される場合もあり、これらに対する耐性も求められている。さらに、重量物を搬送するゴムロールは荷重により変形するという課題があり、改良を求められている。本発明のゴム組成物は、ゴムロールの引張強度や硬度を高めることが可能である。これにより、従来のゴム組成物では困難であった高テンション下で用いられるゴムロールを製造することが可能である。
産業用ケーブルは、電気や光信号を伝送するための線状の部材である。銅や銅合金などの良導体や光ファイバなどを絶縁性の被覆層で被覆したものであり、その構造や設置個所によって、多岐にわたる産業用ケーブルが製造されている。本発明のゴム組成物は、産業用ケーブルの引張強度を高めることが可能である。これにより、従来のゴム組成物では困難であった高負荷がかかる用途でも使用できる産業用ケーブルを製造することができる。
産業用コンベアベルトは、ゴム製、樹脂製、金属製のベルトがあり、多種多様な使用方法に合わせて選定されている。これらの中でもゴム製のコンベアベルトは、安価で多用されているが、特に搬送物との摩擦や衝突の多い環境下で使用すると、劣化による破損などが発生していた。本発明のゴム組成物は、産業用コンベアベルトの引張強度を高めることが可能である。これにより、従来のゴム組成物では困難であった高負荷がかかる環境下で用いられる産業用コンベアベルトを製造することができる。
スポンジは、内部に細かい孔が無数に空いた多孔質の物質であり、具体的には、防振部材、スポンジシール部品、ウェットスーツ、靴などに利用されている。本発明のゴム組成物は、スポンジの引張強度を高めることが可能である。また、クロロプレン系ゴムを用いているためスポンジの難燃性を高めることも可能である。これにより、従来のゴム組成物では困難であった高テンション下で使用されるスポンジや、難燃性に優れたスポンジを製造することができる。さらに、発泡剤の含有量などの調整により得られるスポンジの硬度も適宜調整可能である。
加熱冷却ジャケット及び攪拌機を備えた内容積3Lの重合缶に、クロロプレン(単量体)24質量部、アクリロニトリル(単量体)24質量部、ジエチルキサントゲンジスルフィド0.5質量部、純水200質量部、ロジン酸カリウム(ハリマ化成株式会社製)5.00質量部、水酸化ナトリウム0.40質量部、及び、β-ナフタレンスルホン酸ホルマリン縮合物のナトリウム塩(花王株式会社製)2.0質量部を添加した。次に、重合開始剤として過硫酸カリウム0.1質量部を添加した後、重合温度40℃にて窒素気流下で乳化重合を行った。上述のクロロプレンは、重合開始20秒後から分添し、重合開始からの10秒間の冷媒の熱量変化を元に分添流量を電磁弁で調整し、以降10秒毎に流量を再調節することで連続的に行った。クロロプレン及びアクリロニトリルの合計量に対する重合率が50%となった時点で、重合停止剤であるフェノチアジン0.02質量部を加えて重合を停止させた。その後、減圧下で反応溶液中の未反応の単量体を除去することでクロロプレン-アクリロニトリル共重合体を含む、クロロプレン系ラテックスA-2を得た。
重合率={[(総仕込み量×固形分濃度/100)-蒸発残分]/単量体の仕込み量}×100 ・・・(A)
Mw=8.42×106、1.09×106、7.06×105、4.27×105、1.90×105、9.64×104、3.79×104、1.74×104、2.63×103
以上の製造方法で得られた、クロロプレン系ゴムA-2のアクリロニトリルの単量体単位の含有量は10.0量%であった。
重合工程におけるアクリロニトリル単量体の添加量を変更し、クロロプレン系ゴムに含まれるアクリロニトリル単量体単位の含有量が5.0質量%であるクロロプレン系ゴムA-1、アクリロニトリル単量体単位の含有量が15.0質量%であるクロロプレン系ゴムA-3、アクリロニトリル単量体単位の含有量が20.0質量%であるクロロプレン系ゴムA-4、アクリロニトリル単量体単位の含有量が25.0質量%であるクロロプレン系ゴムA-5を得た。
表1及び表2に記載のように各成分を混合し、8インチオープンロールで混練することにより実施例及び比較例のゴム組成物を得た。
クロロプレン系ゴム:
・上述のクロロプレン系ゴムA-1(クロロプレン・アクリロニトリル共重合体 AN(アクリロニトリル単量体単位)量5質量%)、
・クロロプレン系ゴムA-2(クロロプレン・アクリロニトリル共重合体 AN量10質量%)、
・クロロプレン系ゴムA-3(クロロプレン・アクリロニトリル共重合体 AN量20質量%)、
・クロロプレン系ゴムA-4(クロロプレン・アクリロニトリル共重合体 AN量25質量%)、
・クロロプレン系ゴムA-5(メルカプタン変性クロロプレンゴム(クロロプレンの単独重合体)、デンカ株式会社製「S-40V」)
反応型可塑剤:エポキシ系化合物A(分子量700)、4,5-エポキシシクロヘキサン-1,2-ジカルボン酸ジ(9,10-エポキシステアリル)、新日本理化株式会社、サンソサイザーE-PO
反応型可塑剤:エポキシ系化合物B(分子量370)、ビスフェノールAとエピクロロヒドリンの縮合物、三菱ケミカル株式会社製、JER-828
反応型可塑剤:エポキシ系化合物C(分子量250)、3',4'-エポキシシクロヘキシルメチル 3,4-エポキシシクロヘキサンカルボキシレート、株式会社ダイセル、セロキサイド2021P
反応型可塑剤:エポキシ系化合物D(分子量125)、1-ビニル-3,4-エポキシシクロヘキサン、株式会社ダイセル、セロキサイド2000
反応型可塑剤:エポキシ系化合物E(分子量Mw≧900)、エポキシ基含有ポリブタジエンゴム、日本曹達株式会社、JP-100
可塑剤:エーテルエステル系化合物、株式会社ADEKA製、アデカサイザーRS-700、
充填材:カーボンブラック(HAF)、旭カーボン株式会社製「旭#70」
充填材:シリカ、東ソー・シリカ株式会社、Nipsil AQ
シランカップリング剤:メタクリロキシプロピルトリメトキシシラン、信越化学工業株式会社、KBM-503
ハイドロタルサイト:化学式 Mg4.3Al2(OH)12.6CO3・3.5H2O、協和化学工業株式会社、DHT-4A
加工助剤:ステアリン酸:新日本理化株式会社製、ステアリン酸50S
酸化亜鉛:堺化学工業株式会社製、酸化亜鉛2種
有機過酸化物:1,4-ビス[(t-ブチルパーオキシ)イソプロピル]ベンゼン、日本油脂株式会社、パーブチルP
耐熱老化防止剤:4,4'-ビス(α、α-ジメチルベンジル)ジフェニルアミン、大内新興化学工業株式会社、ノクラックCD
硬化剤:カルボン酸ジヒドラジド、大塚化学株式会社、イソフタル酸ジヒドラジド
(スコーチタイム)
JIS K 6300-1に基づき、L型ロータ、試験温度125℃でムーニースコーチ試験を実施した。測定ムーニー粘度が5M増えた時間をスコーチタイムとした。得られたスコーチタイムを以下の評価基準で評価した。
A:11分以上
B:9分以上、11分未満
C:7分以上、9分未満
D:7分未満
得られたゴム組成物をJIS K6299に基づき、160℃×40分の条件でプレス加硫することにより厚さ2mmのシート状の加硫成形体を作製した。
上述の加硫成形体の評価を以下のとおり行った。結果を表1及び表2に示す。
JIS K 6251に基づき、上述のシート状の加硫成形体を厚さ2mmのダンベル状3号形試験片に成形し、5枚の試験片を準備した。株式会社島津製作所製の加硫ゴム用長ストローク引張試験システムを用いて、引張速度500mm/minで各試験片の引張強度を測定した。得られた引張強度を以下の評価基準で評価した。
A:25MPa以上
B:23MPa以上、25MPa未満
C:21MPa以上、23MPa未満
D:21MPa未満
上述のシート状の加硫成形体を、アスカーゴム硬度計A型(高分子計器株式会社)を用いて、JIS K 6253で規定されるデュロメータ硬度(タイプA)を測定した。得られた硬度を以下の評価基準で評価した(デュロメータ硬度測定の詳細は、JIS K 6253-3)。
A:90以上
B:85以上、90未満
C:80以上、85未満
D:80未満
JIS K 6261に基づき、ゲーマンねじり試験を行い、T10を求めた。上述の加硫成形体について、180°ねじりモジュラスが、常温における180°ねじりモジュラスの10倍になる温度(T10)を求めた。得られたT10を以下の基準で評価した。
A:-30℃未満
B:-30℃以上、-20℃未満
C:-20℃以上、-10℃未満
D:-10℃以上
Claims (8)
- 不飽和ニトリル単量体単位の含有率が25質量%未満であるクロロプレン系ゴム、及び重量平均分子量が100を超え900未満のエポキシ系化合物を含むゴム組成物であって、
前記クロロプレン系ゴム100質量部に対して、前記エポキシ系化合物を0.1~25質量部含有するゴム組成物。 - 前記不飽和ニトリル単量体がアクリロニトリルである、請求項1に記載のゴム組成物。
- 前記エポキシ系化合物が、脂環式エポキシ化合物、エピクロロヒドリンとビスフェノールとの共重合体からなるエポキシ樹脂、及び、エポキシ化不飽和脂肪酸エステルから選ばれる少なくとも1種のエポキシ系化合物である、請求項1または請求項2に記載のゴム組成物。
- 前記クロロプレン系ゴム100質量部に対して、充填材を20~80質量部含有する、請求項1または請求項2に記載のゴム組成物。
- 前記エポキシ系化合物100質量部に対して、硬化剤を5質量部以上含有する、請求項1または請求項2に記載のゴム組成物。
- 前記ゴム組成物を、JIS K6299に基づき成形して得た加硫物の、JIS K6253に基づき測定したタイプAデュロメータ硬度が80以上である、請求項1または請求項2に記載のゴム組成物。
- 請求項1または請求項2に記載のゴム組成物の加硫物。
- 請求項7に記載の加硫物を用いた加硫成形体。
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- 2022-09-07 EP EP22869874.2A patent/EP4378993A1/en active Pending
- 2022-09-07 KR KR1020247012181A patent/KR20240056597A/ko unknown
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JPH08245842A (ja) * | 1995-03-13 | 1996-09-24 | Nichias Corp | 加硫ゴム組成物 |
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WO2022091518A1 (ja) * | 2020-10-26 | 2022-05-05 | デンカ株式会社 | ゴム組成物、加硫物及び加硫成形体 |
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