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WO1999050349A1 - Composition de caoutchouc pour production de tuyaux flexibles et tuyau flexible - Google Patents

Composition de caoutchouc pour production de tuyaux flexibles et tuyau flexible Download PDF

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Publication number
WO1999050349A1
WO1999050349A1 PCT/JP1999/001624 JP9901624W WO9950349A1 WO 1999050349 A1 WO1999050349 A1 WO 1999050349A1 JP 9901624 W JP9901624 W JP 9901624W WO 9950349 A1 WO9950349 A1 WO 9950349A1
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WO
WIPO (PCT)
Prior art keywords
rubber
rubber composition
composition according
acrylate
hose
Prior art date
Application number
PCT/JP1999/001624
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English (en)
Japanese (ja)
Inventor
Mitsunori Abe
Daisuke Tsugawa
Original Assignee
Nippon Zeon Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nippon Zeon Co., Ltd. filed Critical Nippon Zeon Co., Ltd.
Publication of WO1999050349A1 publication Critical patent/WO1999050349A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59

Definitions

  • the present invention relates to a rubber composition for producing a hose and a hose produced by using the rubber composition. More specifically, the present invention relates to an acrylic rubber copolymerized with a monoester fumarate as a carboxyl group-containing monomer. The present invention relates to a rubber composition for producing an oil-resistant hose to be used, and an oil-resistant hose produced by using the rubber composition. Background technology
  • Oil-resistant hoses are generally manufactured by steam vulcanization after molding into a hose shape using acrylate copolymer rubber such as epoxy group-containing acrylic rubber or ethylene-acrylate copolymer rubber as raw material rubber. ing.
  • an oil-resistant hose using acryl rubber obtained by copolymerizing a monoalkyl maleate as a carboxyl group-containing monomer as a raw rubber is disclosed in Japanese Patent Application Laid-Open No. 6-95915. Have been. In this hose, the deterioration of vulcanization properties due to steam vulcanization and the adhesiveness during extrusion molding are improved.
  • hoses made of acryl rubber copolymerized with a monoalkyl maleate as a raw material rubber have a problem in that the pressure resistance, particularly after heat load, is insufficient.
  • JP-A-50-45031 discloses a butenedioic acid monoester such as maleic acid monoalkyl ester and acrylic acid alkyl ester, or acryl rubber obtained by copolymerizing these with ethylene. . These acrylic rubbers In the vulcanizable composition using the composition, scorch hardly occurs. However, the physical properties of the vulcanized product obtained by press vulcanizing the vulcanizable composition are not known, and the physical properties of the steam vulcanized product are not known. Disclosure of the invention
  • the present invention provides a rubber composition for producing an oil-resistant hose, in which a steam vulcanizate has the same vulcanizate properties as a press vulcanizate, and has a small decrease in pressure resistance after heat load. It is to provide a manufactured oil resistant hose.
  • the present inventors have conducted studies to achieve the above object in consideration of these known techniques, and as a result, as a carboxyl group-containing monomer, fumaric acid monoester is relatively coexistent with alkyl acrylate.
  • the present inventors have found that the object can be achieved by using acryl rubber which can be polymerized and obtained, and have completed the present invention.
  • a rubber composition for an oil-resistant hose comprising an acryl rubber obtained by copolymerizing an alkyl acrylate and a monoester of fumaric acid, and a vulcanizing agent, and a rubber composition for a hose.
  • An oil-resistant hose formed and vulcanized is provided.
  • the acryl rubber used in the present invention is obtained by polymerizing a monomer mixture containing a monoester of fumaric acid and an alkyl acrylate, and preferably polymerizing a monomer mixture containing these and an alkoxyalkyl acrylate. That is what we do.
  • Examples of the monoester of fumaric acid in the present invention include monomethyl fumarate, monoethyl fumarate, mono-n-propyl fumarate, monoisopropyl fumarate, mono-n-butyl fumarate, isobutyl fumarate, ter-butyl fumarate, ter-butyl fumarate, and fumarate Alkyl-based carbons such as mono-n-amyl fumarate, mono-n-hexyl fumarate, mono-n-heptyl fumarate, mono-n-hexyl fumarate, and mono- (2-ethylhexyl) fumarate Monoalkyl fumarate having a number of 1 to 10; monomethoxymethyl fumarate, monomethoxyl fumarate, monoethoxyxethyl fumarate, fumarate Monoalkoxyalkyl fumarate having an alkylene group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon
  • monomethyl fumarate monoethyl fumarate, mono-n-propyl fumarate, mono-n-butyl fumarate, monomethoxymethyl fumarate, monomethoxethyl fumarate, and more preferably monoethyl fumarate and mono-n-fumarate —Butyl and the like.
  • the alkyl acrylate to be copolymerized with the fumaric acid monoester is not particularly limited, and those conventionally used in known acrylic rubbers can be used.
  • alkyl acrylates having an alkyl group having 1 to 10 carbon atoms such as 2-cyanoethyl acrylate. Of these, acrylate ethyl ester or ⁇
  • the alkoxyalkyl acrylate used together with the alkyl acrylate is not particularly limited, and those used in conventionally known acrylic rubbers can be used.
  • An alkoxyalkyl acrylate having an alkylene group having 1 to 5 carbon atoms and an alkoxy group having 1 to 5 carbon atoms is exemplified. Among them, acrylic acid 2-methoxethyl ester and acrylic acid 2-ethoxyethyl ester are preferred.
  • alkoxyalkyl acrylates can be used alone or in combination of two or more.
  • a monomer copolymerizable with the above monomer can be used in the present invention.
  • examples of such a monomer include a, / 3-unsaturated nitrile monomer such as acrylonitrile and methacrylonitrile.
  • ⁇ -olefins such as ethylene and propylene
  • aromatic vinyl monomers such as styrene and ⁇ -methylstyrene
  • vinyls such as vinyl chloride, vinylidene chloride, vinyl acetate, ethyl vinyl ether, and butyl vinyl ether
  • monomers that are derivatives of acrylic acid and methacrylic acid such as alkoxyalkyl methacrylate, furfuryl acrylate, acrylamide, etc .
  • monomers such as isoprene, butadiene, chloroprene, piperylene, etc.
  • Conjugated diene monomer dicyclopentene, norbornene, ethylidene norbo
  • Non-conjugated diene monomers such as nene, hexadiene, norbornadiene; polyfunctional such as divinylbenzene, ethylene glycol diacrylate, propylene glycol diacrylate, ethylene glycol dimethacrylate, propylene glycol dimethacrylate Monomers. These can be used alone or in combination of two or more.
  • the acryl rubber used in the present invention can be obtained by radical polymerization of the above monomer in the same manner as ordinary polymerization of acryl rubber.
  • polymerization forms such as emulsion polymerization, solution polymerization, and suspension polymerization, polymerization systems such as batch system and continuous system, polymerization conditions such as polymerization temperature, and recovery methods are not particularly limited. It may be.
  • the proportion of each monomer in the monomer mixture at the time of producing the acryl rubber used in the present invention is appropriately determined according to the characteristics required for a hose using the acryl rubber, and is not particularly limited.
  • the proportion of the fumaric acid monoester in the monomer mixture is preferably from 0.1 to 40% by weight, more preferably from 0.2 to 20% by weight, particularly preferably from 0.5 to 10% by weight. .
  • the proportion of alkyl acrylate in the monomer mixture is preferably from 10 to 99.9% by weight, more preferably from 50 to 97.8% by weight, particularly preferably from 70 to 94.5% by weight. %.
  • the proportion of the alkoxyalkyl acrylate in the monomer mixture is preferably 0 to 50% by weight, more preferably 2 to 30% by weight, particularly preferably 2 to 30% by weight. Preferably it is 5 to 20% by weight. Can be copolymerized with these monomers if necessary ⁇
  • the monomer can be used within a range that does not impair the inherent properties of acryl rubber.
  • the unit amount of each monomer in the acryl rubber used in the present invention thus obtained coincides with the amount of each monomer used in the above-mentioned polymerization (the amount charged during the polymerization).
  • the acrylic rubber used in the present invention has a viscosity of ML (ML 1 + 4 , 100 ° C), preferably from 10 to 150, more preferably from 15 to 100, and particularly preferably from 15 to 100. Preferably it is 20 to 60.
  • the amount of the fumaric acid monoester unit in the acryl rubber used in the present invention is preferably 0.0005 to 0.06 mol, more preferably 0 mol, based on the amount of carboxyl groups (ephr) in 100 g of the acryl rubber. 0.003 to 0.020 mol, particularly preferably 0.05 to 0.010 mol. If the amount of the fumaric acid monoester unit is too small, vulcanization becomes insufficient, and it is difficult to use as a vulcanized rubber. On the other hand, if the amount of fumaric acid monoester unit is too large, vulcanization will be excessive, elongation will be reduced, and strength and heat resistance will be insufficient.
  • the rubber composition for producing a hose of the present invention is obtained by blending a vulcanizing agent with the above acryl rubber.
  • vulcanization is originally used when vulcanizing an unsaturated rubber such as a gen-based rubber with sulfur or a sulfur-donating compound as a vulcanizing agent.
  • unsaturated rubber such as a gen-based rubber with sulfur or a sulfur-donating compound
  • these cross-linking agents are called vulcanizing agents, and cross-linking is called vulcanization. Therefore, also in the present invention, the crosslinking agent is referred to as a vulcanizing agent, and the crosslinking is referred to as vulcanizing.
  • any conventionally known vulcanizing agent used for vulcanizing a carboxyl group-containing acryl rubber can be used, and is not particularly limited.
  • Preferred vulcanizing agents include, for example, primary amines such as polyvalent aliphatic primary amines and polyvalent aromatic primary amines and derivatives thereof, and compounds containing a polyhydrazide group.
  • primary amines such as polyvalent aliphatic primary amines and polyvalent aromatic primary amines and derivatives thereof, and compounds containing a polyhydrazide group.
  • polyvalent aliphatic primary amines and derivatives thereof include hexamethylene diamine, hexamethylene diamine carbamate, tetramethylene pentamine, and g
  • Xamethylene diamine-cinnamaldehyde condensate and hexamethylene diamine-dibenzoate salt and the like examples include aromatic primary amines include 4, 4'-methylene dianiline, 4 , 4'-diaminodiphenyl ether, m-phenylenediamine, p-phenylenediamine, 4,4'-methylenebis (o-chloroaniline) and the like. Of these, hexamethylene diamine carbamate, hexamethylene diamine-cinnam aldehyde condensate, 4,4'-methylene dianiline, and 4,4 'diamino diphenyl ether are preferred. These can be used alone or in combination of two or more.
  • polyhydrazide group-containing compounds include, for example, isophthalic acid dihydrazide, terephthalic acid dihydrazide, phthalic acid dihydrazide, 2,6-dinaphthalenedene diluphthalide, ruponic acid dihydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, azidipine Reaction products of carboxylic acids such as aliphatic carboxylic acids and aromatic carboxylic acids such as acid dihydrazide, sebacic acid dihydrazide, maleic acid dihydrazide and fumaric acid hydrazide with hydrazine. These can be used alone or in combination of two or more.
  • a vulcanizing agent is often used together with a vulcanization accelerator, and the use of a vulcanization accelerator is also desirable in the present invention.
  • Examples of the vulcanization accelerator include (1) alkali metal salts and alkali metal hydroxides of inorganic weak acids (eg, sodium hydroxide, sodium carbonate, potassium hydroxide, sodium hydrogen carbonate, etc.), (2) organic weak acids Alkali metal salts, alkali metal alcoholates and phenolates (eg, sodium stearate, potassium stearate, sodium laurate, sodium benzoate, sodium ethoxide, etc.); Penium salts and quaternary phosphonium salts, hydroxides, alcoholates, phenolates, etc.
  • alkali metal salts and alkali metal hydroxides of inorganic weak acids eg, sodium hydroxide, sodium carbonate, potassium hydroxide, sodium hydrogen carbonate, etc.
  • organic weak acids Alkali metal salts, alkali metal alcoholates and phenolates (eg, sodium stearate, potassium stearate, sodium laurate, sodium benzoate, sodium ethoxide, etc.)
  • Guanidines (diphenylguanidine, di-O-tolylguanidine, tetramethylguanidine, dibutyldanidine, etc.), (6) Heterocyclic tertiary amines (imidazole, pyridine, quinoline, etc.) Is mentioned. These can be used alone or in combination of two or more.
  • the amount of the vulcanizing agent is not particularly limited, but is preferably 0.1 to 10 parts by weight, more preferably 0.2 to 5 parts by weight, per 100 parts by weight of the acrylic rubber. If the amount of the vulcanizing agent is too small, it is difficult to obtain a vulcanizate having satisfactory tensile strength due to insufficient vulcanization, and if the amount of the vulcanizing agent is too large, the vulcanized product is hard. Too much, and the decrease in elongation becomes large.
  • the amount of the vulcanizing agent used is a general guide. More precisely, the amount of the functional group in the vulcanizing agent used per 100 g of the acrylic rubber is preferably 0.000.
  • the amount of the vulcanizing agent is adjusted so as to be 0.2 to 0.1 mol, more preferably 0.005 to 0.035 mol, and particularly preferably 0.02 to 0.02 mol. Decide.
  • the amount of the vulcanization accelerator used is preferably from 0.1 to 20 parts by weight, more preferably from 0.2 to 10 parts by weight, particularly preferably from 0 to 100 parts by weight, per 100 parts by weight of the acryl rubber of the present invention. 4 to 5 parts by weight. If the amount of the vulcanization accelerator is too small, it is difficult to obtain a vulcanizate with insufficient vulcanization and satisfactory tensile strength, and if the amount of the vulcanization accelerator is too large, the vulcanization properties may be reduced. The improvement effect is small and lacks processing stability.
  • the rubber composition for producing an oil-resistant hose of the present invention can be produced by mixing the acrylic rubber and the vulcanizing agent together with other compounding agents, if necessary. Mixing is usually performed by kneading using a mixer such as a roll, a Banbury or an internal mixer.
  • compounding agents include, for example, reinforcing materials, fillers, anti-aging agents, antioxidants, light stabilizers, anti-scorch agents, crosslinking retarders, plasticizers, processing aids, lubricants, adhesives, lubricants , A flame retardant, a fungicide, an antistatic agent, a coloring agent, and the like.
  • the type and amount of these compounding agents are not particularly limited, and the characteristics required for an oil-resistant hose are not limited. It can be determined appropriately depending on the situation.
  • Other rubber components include, for example, acrylic rubber other than the above acrylic rubber, ethylene-acrylate copolymer rubber, olefin rubber such as EPDM, natural rubber, polybutadiene rubber, polyisoprene rubber, styrene-butadiene copolymer Rubber, acrylonitrile-butadiene copolymer rubber, chloroprene rubber, vinyl chloride-based elastomer, polyester-based elastomer, polyamide-based elastomer, polyurethane-based elastomer, polysiloxane-based elastomer, and the like.
  • the use of ethylene acrylate copolymer rubber is preferred.
  • Ethylene monoacrylate copolymer rubber is obtained by copolymerizing ethylene and at least one of the above-mentioned alkyl acrylates or at least one of the above-mentioned alkoxy acrylates, and a monomer for a crosslinking site. This is the rubber obtained.
  • the proportion of each of these monomers used in the production of the copolymer rubber is not particularly limited.
  • the ethylene is preferably 20 to 75% by weight, more preferably 30 to 65% by weight, and still more preferably.
  • the crosslinked site monomer preferably 0 to 30% by weight of the crosslinked site monomer, more preferably 0.5 to 15% by weight, still more preferably 3 to 5% by weight, acrylic acid It is a copolymer rubber obtained by copolymerizing a monomer mixture with the remaining alkyl ester.
  • the alkyl acrylate is preferably methyl acrylate or ethyl acrylate.
  • butenedioic acid monoesters such as monoalkyl maleate, monoalkoxyalkyl maleate, monoalkyl fumarate and monoalkoxyalkyl fumarate are preferred.
  • the monoester in this case is the same as the above-mentioned monoester of fumaric acid monoester.
  • the proportions of these crosslinking site monomers used are the same as those used in the acrylic rubber of the present invention.
  • the Mooney viscosity of the ethylene-acrylate copolymer rubber is the same as that of the acryl rubber used in the present invention.
  • the acryl rubber is preferably 50 to 90% by weight, more preferably 70 to 85% by weight.
  • the copolymer rubber is preferably used in a mixture of 10 to 50% by weight, more preferably 15 to 30% by weight.
  • the copolymer rubber which has not been used can also be used.
  • the ethylene-acrylate copolymer rubber When the ethylene-acrylate copolymer rubber is cross-linked, it can be cross-linked using a cross-linking agent different from the acrylic rubber used in the present invention, but is preferably co-cross-linked with the same cross-linking agent as the acryl rubber.
  • the amounts of the cross-linking agent and the cross-linking accelerator used are appropriately adjusted so as to satisfy the performance required for the oil-resistant rubber hose.
  • a method for producing a hose using the rubber composition for producing a hose of the present invention may be in accordance with a conventionally known method for producing a hose, and is not particularly limited.
  • the structure of the hose is not particularly limited, and may be, for example, a fiber coating, a thread core, or a laminate with another rubber or resin.
  • a hose is formed by extruding a rubber composition into a hose shape using an extruder, performing primary vulcanization by steam vulcanization in a vulcanizer, and then performing secondary vulcanization under hot air in an oven. Manufactured in.
  • the hose of the present invention can be used, for example, as an oil-resistant hose such as an automotive fuel hose, an automotive ATF hose, and an educt hose.
  • the acryl rubber copolymerized with fumaric acid monoester used in the present invention and the acryl rubber of Comparative Example were produced by ordinary emulsion polymerization.
  • Table 1 shows the monomer composition of each of the acrylic rubbers and the amount of carboxylic acid groups in the rubbers.
  • Each vulcanizable rubber composition is press-vulcanized (primary vulcanization: 160 ° C, 30 minutes) to obtain a vulcanized sheet having a thickness of 2 mm, which is then secondary vulcanized with heated air ( (170 ° C, 4 hours).
  • the vulcanization conditions for steam vulcanization in a vulcanizer as the primary vulcanization are the same as the above-mentioned primary vulcanization conditions.
  • Copolymer rubber (1) 20 20 20 20 20 20 20 20 20 20 20 20
  • Tree t ⁇ tree + direction tree ⁇ tree f ⁇ tree 1 ⁇ tree ⁇
  • MAF carbon black (2) 60 60 60 60 60 60 60 60 Filling, linoleic acid 1 1 1 1 1 1 1 Lubricant (3) 2 2 2 2 2 2 Caro sulfurizer DPE (4) 0.44 0.42 0.45
  • hoses were produced by performing primary vulcanization by steam vulcanization and secondary vulcanization in an oven. All of the hoses made of the rubber composition of the comparative example showed a large decrease in the tensile strength after heat load as compared to the tensile strength in the state, which hindered use, whereas the hose of the present invention It was confirmed that the hose of the present invention under normal conditions and after heat load had excellent tensile strength.
  • the ethylene rubber is used as It can be seen that by blending the acrylate copolymer rubber, a vulcanizate having a high tensile strength and an excellent performance with a very small elongation change after thermal aging can be obtained.
  • the rubber composition for manufacturing a hose of the present invention When the rubber composition for manufacturing a hose of the present invention is used, the decrease in strength after heat load is remarkably small even in the case of steam vulcanization, as in the case of press vulcanization or vulcanization under heated air. A hose with excellent strength retention and excellent oil resistance can be obtained.
  • the hose of the present invention thus manufactured is suitable for an oil-resistant hose for transferring various control oils such as ATF oil transfer and power steering.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Rigid Pipes And Flexible Pipes (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)

Abstract

L'invention concerne une composition de caoutchouc destinée à produire un tuyau flexible résistant à l'huile, qui comporte un caoutchouc acrylique obtenu par polymérisation d'un mélange monomère comprenant un monoester fumarique, un acrylate d'alkyle et un agent de vulcanisation.
PCT/JP1999/001624 1998-03-30 1999-03-30 Composition de caoutchouc pour production de tuyaux flexibles et tuyau flexible WO1999050349A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
JP10/83713 1998-03-30
JP8371398 1998-03-30
JP29830198A JPH11343378A (ja) 1998-03-30 1998-10-20 耐油性ホース用ゴム組成物及び耐油性ホース
JP10/298301 1998-10-20

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WO1999050349A1 true WO1999050349A1 (fr) 1999-10-07

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1334995A1 (fr) * 2002-02-12 2003-08-13 Tokai Rubber Industries, Ltd. Compositions de caoutchouc acrylique et tuyaux thermo-résistants

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP4505913B2 (ja) * 1999-12-24 2010-07-21 ユニマテック株式会社 アクリル系エラストマー組成物およびその架橋性組成物
JP4273671B2 (ja) * 2001-03-06 2009-06-03 日本ゼオン株式会社 アクリルゴム組成物および加硫物
US7153918B2 (en) 2003-07-24 2006-12-26 E. I. Du Pont De Nemours And Company Random ethylene/alkyl acrylate copolymers, compounds and elastomeric compositions thereof with improved low temperature properties
US7521503B2 (en) 2003-07-24 2009-04-21 E. I. Du Pont De Nemours And Company Ethylene/alkyl acrylate copolymers, compounds and vulcanizates thereof
US7544757B2 (en) 2005-06-30 2009-06-09 E. I. Du Pont De Nemours And Company Ethylene/alkyl acrylate copolymers and compounds, vulcanizates and articles thereof
CN101253204B (zh) 2005-06-30 2012-05-23 纳幕尔杜邦公司 乙烯/丙烯酸烷基酯共聚物和其胶料和硫化橡胶
JP5433970B2 (ja) * 2008-04-11 2014-03-05 Ｎｏｋ株式会社 アクリルゴム組成物
EP3985039B1 (fr) * 2019-06-13 2024-04-24 Unimatec Co., Ltd. Caoutchouc acrylique et composition réticulable de ce dernier

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5045031A (fr) * 1973-08-09 1975-04-22
JPS62116651A (ja) * 1985-08-30 1987-05-28 Japan Synthetic Rubber Co Ltd 加硫ゴム組成物
JPH1192614A (ja) * 1997-09-19 1999-04-06 Nippon Mektron Ltd アクリルエラストマー組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5045031A (fr) * 1973-08-09 1975-04-22
JPS62116651A (ja) * 1985-08-30 1987-05-28 Japan Synthetic Rubber Co Ltd 加硫ゴム組成物
JPH1192614A (ja) * 1997-09-19 1999-04-06 Nippon Mektron Ltd アクリルエラストマー組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1334995A1 (fr) * 2002-02-12 2003-08-13 Tokai Rubber Industries, Ltd. Compositions de caoutchouc acrylique et tuyaux thermo-résistants

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