WO2005087704A1 - 化合物及びそれを含む組成物 - Google Patents
化合物及びそれを含む組成物 Download PDFInfo
- Publication number
- WO2005087704A1 WO2005087704A1 PCT/JP2005/003899 JP2005003899W WO2005087704A1 WO 2005087704 A1 WO2005087704 A1 WO 2005087704A1 JP 2005003899 W JP2005003899 W JP 2005003899W WO 2005087704 A1 WO2005087704 A1 WO 2005087704A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- general formula
- compound represented
- bis
- compound
- hydroxyphenyl
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/50—Sebacic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/40—Succinic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/34—Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom
- C07C69/44—Adipic acid esters
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
Definitions
- the present invention relates to a novel composition or compound for improving the adhesion durability to a metal reinforcing material such as a steel cord used for rubber articles such as pneumatic tires and industrial belts.
- the rubber composition has good processability when blended with the rubber composition, and can exhibit initial adhesion and wet heat resistance to a metal reinforcing material stably regardless of the storage period of the rubber composition.
- the present invention relates to a compound having a specific structure and a composition containing the compound as a main component.
- RF resin resorcinol or resorcinol formaldehyde resin
- resorcinol and RF resin have very high polarity, and therefore have poor compatibility with rubber. Therefore, depending on conditions such as mixing, blending, and storage, resorcinol and RF resin are precipitated by so-called bloom. , The appearance of the rubber article may be impaired. In addition, due to the blooming, the adhesive property decreases when the rubber composition is blended and stored for a long time until vulcanization bonding. Then, since a problem arises, the rubber composition containing resorcinol and RF resin needs to be quickly vulcanized and bonded, which may impair the productivity of rubber articles.
- an adhesive material comprising a mixed polyester resin having a resorcinol skeleton having a weight average molecular weight of 3000 to 45000 has been reported (JP-A-7-118621).
- mixed polyesters with higher molecular weights have improved compatibility with rubber compared to RF resins, but have not been completely satisfactory.
- a high-molecular weight mixed polyester is compounded with rubber, there is a problem that the viscosity of the compounded rubber increases and the processability decreases, and the wet heat and heat resistance is also insufficient.
- the rubber composition when compounded with rubber has high processability and high! ⁇ While maintaining moisture and heat resistance, the bloom seen when resorcinol or RF resin is blended is suppressed as much as possible, and the decrease in adhesion during storage of the rubber composition can be reduced, resulting in excellent adhesion stability. It is an object of the present invention to provide a compound having a specific structure and a composition containing the compound as a main component.
- the present inventors have conducted intensive studies to achieve the above object, and as a result, by compounding a rubber with a compound having a specific structure or a composition containing the compound as a main component, it has been found that resorcinol and RF resin can be mixed with rubber. While maintaining the same or better wet and heat resistance, it maintains the processability of the rubber composition obtained by compounding it with rubber, which is a problem with resorcinol and RF resin, and suppresses blooming, compounding and storage. It has been found that excellent adhesion stability is exhibited irrespective of the conditions such as the above, and the present invention has been completed.
- the present invention provides:
- R represents a divalent aliphatic group having 11 to 16 carbon atoms.
- R represents a divalent aliphatic group having 11 to 16 carbon atoms.
- the composition does not include a pure substance in which the compound represented by the general formula (2) is 100% by weight.
- R represents a divalent aliphatic group having 11 to 16 carbon atoms, and n represents an integer of 2 to 6).
- the rubber composition obtained by compounding with rubber keeps the processability and the high heat-moisture and heat-resistant adhesion while minimizing the bloom seen when resorcinol or RF resin is compounded.
- R in the general formula (1) represents a divalent aliphatic group having 1 to 16 carbon atoms.
- Examples of the compound represented by the general formula (1) include a compound represented by the general formula (2).
- R in the general formula (2) has the same meaning as R in the general formula (1).
- examples of the divalent aliphatic group having 1 to 16 carbon atoms include a methylene group and an ethylene group.
- Butylene, isobutylene, otathylene, 2-ethylhexylene, etc. Is a straight-chain or branched-chain alkylene group such as a branched alkylene group, a biylene group (ethylene group), a butylene group, and an otate-len group; a hydrogen atom of the alkylene group or the alkylene group.
- Examples thereof include an alicyclic group such as an alkylene group in which an atom is substituted with a hydroxyl group or an amino group, an alkenylene group, and a cyclohexylene group.
- an alkylene group having 2 to 10 carbon atoms is more preferable, and an ethylene group, a butylene group or an otaylene group is particularly preferable.
- Specific examples of the compound represented by the general formula (1) include bis (2-hydroxyphenyl) malonate, bis (2-hydroxyphenyl) succinate, and bis (2-hydroxyphenyl) fumarate.
- -Ester bis (2-hydroxyphenyl) maleate, bis (2-hydroxyphenyl) malate, bis (2-hydroxyphenyl) itaconate, bis (2-hydroxyphenyl) citrate —Hydroxyphenyl) ester, bis (2-hydroxyphenyl) adipate, bis (2-hydroxyphenyl) tartrate, bis (2-hydroxyphenyl) azelate, bis (sebacate) 2-Hydroxyphenyl) ester, bis (2-hydroxyphenyl) cyclohexanedicanolevonate, bis (3-hydroxyphenyl) malonate Ter, bis (3-hydroxyphenyl) succinate, bis (3-hydroxyphenyl) fumarate, bis (3-hydroxyphenyl) maleate, bis (3-hydroxyphenyl) phosphate -Ester
- the method for producing the compound represented by the general formula (1) is not particularly limited.
- R represents a divalent aliphatic group having 1-16 carbon atoms
- X represents a halogen atom.
- a compound represented by the following general formula (5) ... (5) is produced by reacting in the presence or absence of a base.
- R in the general formula (4) has the same meaning as R in the general formula (1), and X represents a halogen atom.
- a halogen atom a chlorine atom or a bromine atom is preferable.
- Examples of the compound represented by the general formula (4) include malonic acid dichloride, succinic acid dichloride, fumaric acid dichloride, maleic acid dichloride, glutaric acid dichloride, adipic acid dichloride, suberic acid dichloride, azelaic acid dichloride, Sebacic acid dichloride, 1,10-decanedicarboxylic acid dichloride, 1,12-dodecanedicarboxylic acid dichloride Alicyclic dicarboxylic acid dichlorides, such as 1,1,6-hexadecane dicarboxylic acid dichloride, etc., aliphatic dicarboxylic acid dichloride, cyclohexane dicarboxylic acid dichloride, cyclohexene dicarboxylic acid dichloride, malonic acid dibromide, succinic acid dibromide , Fumaric acid dibromide, maleic acid dibromide, glutaric acid dibromide, adip
- malonic acid dichloride succinic acid dichloride, adipic acid dichloride, azelaic acid dichloride, sebacic acid dichloride, malonic acid dibromide, succinic acid dibromide, adipic acid dibromide, azelaic dibromide, dibromide sebacic acid, etc. Is preferred.
- examples of the compound represented by the general formula (5) include catechol, resorcin, and hydroquinone.
- the base used when reacting the compound represented by the general formula (4) with the compound represented by the general formula (5) is usually pyridine, j8-picoline, N-methylmorpholine, Organic bases such as dimethylaniline, getylaniline, trimethylamine, triethylamine and tributylamine are used.
- the compound represented by the general formula (4) and the compound represented by the general formula (5) are usually used.
- the compounds represented by the formula are reacted in a molar ratio of 1: 4 to 1:30.
- a solvent can be used for the purpose of dissolving the raw materials and the like.
- the above-described organic base may be used as it is, or another organic solvent that does not inhibit the reaction may be used.
- examples of such a solvent include ether solvents such as dimethyl ether and dioxane.
- the reaction temperature at the time of reacting the compound represented by the general formula (4) with the compound represented by the general formula (5) is usually from ⁇ 20 ° C. to 100 ° C.
- the compound represented by the general formula (1) obtained by the above reaction can be isolated from the reaction mixture by a known method. That is, the organic base used in the reaction and the compound represented by the general formula (5), and if an organic solvent is used in the reaction, the organic solvent is distilled off to dryness by an operation such as vacuum distillation. A method of adding a poor solvent of the compound represented by the general formula (1) to the reaction mixture to cause reprecipitation, and adding water and water to the reaction mixture. ⁇ Adding an organic solvent and extracting into an organic layer And the like. In some cases, it may be purified by recrystallization.
- water As a poor solvent for the compound represented by the general formula (1), water is usually used.
- the water-immiscible organic solvent include esters such as ethyl acetate and butyl acetate, and ketones such as methyl isobutyl ketone and diisobutyl ketone.
- the compound represented by the general formula (2) is mainly composed of the compound represented by the general formula (2).
- a composition comprising the compound represented by the formula (3) is obtained.
- R in the general formula (3) has the same meaning as R in the general formula (1), and n represents an integer of 2-6.
- a composition comprising the compound represented by the general formula (2) and the compound represented by the general formula (3) is also similar to the method for isolating the compound represented by the general formula (1). Can be isolated from a reaction mixture containing these.
- the wet heat adhesion when compounded with rubber and bonded is improved.
- the content of the compound represented by the general formula (2) is more preferably from 70 to 100% by weight, and even more preferably from 80 to 100% by weight.
- the compound of the present invention and a composition containing the compound as a main component include resorcinol and RF resin. It has the characteristic that it is easily mixed with rubber components. Therefore, a rubber composition containing the compound of the present invention or a composition containing the compound as a main component tends to be less likely to bloom than a rubber composition containing resorcinol or RF resin. This is presumably because the compound of the present invention and the composition containing the compound as a main component have a lower polarity than resorcinol and RF resin. Further, the rubber composition containing the compound of the present invention and a composition containing the compound as a main component has excellent adhesion stability regardless of the storage period. Therefore, the compound of the present invention and a composition containing the compound as a main component are useful as an adhesion improver.
- a solution of 330.6 g (3.0 mol) of resorcinol in 600 Og of pyridine was kept at 15 ° C. or lower on an ice bath, and 54.9 g (0.30 mol) of adiboyl chloride was gradually added dropwise thereto. After the completion of the dropwise addition, the obtained reaction mixture was heated to room temperature, and left standing for one day to complete the reaction. Pyridine was distilled off from the reaction mixture under reduced pressure, and 1200 g of water was added to the residue. The deposited precipitate was filtered and washed with water, and the obtained wet body was dried under reduced pressure to obtain 84 g of a white light yellow powder.
- This powder was treated by liquid chromatography equipped with a fractionating device under the following conditions, and an eluent containing the main components was fractionated.
- the eluate was concentrated, and the precipitated crystals were collected by filtration and dried under reduced pressure to obtain crystals having a melting point of 140 to 143 ° C.
- the crystals were bis (3-hydroxyphenyl) adipate having a purity of 98%.
- HPLC conditions for the fractionation are as follows.
- the measurement conditions of the MS spectrum are as follows.
- n 2: 555.1 [M + H] +, 568.2 [M + NH4] +
- n 3: 771.2 [M + H] +, 788.2 [M + NH4] +
- HPLC analysis conditions are as follows.
- the obtained organic layer was washed five times with cold water, and then dried with magnesium sulfate. Thereafter, 500 g of toluene was added to the viscous substance obtained by distilling off the ethyl acetate to crystallize, filtered, washed with toluene, and sludged twice with 1 L of water. After dissolving the obtained wet body in 100 g of methanol, 1 L of water was charged and reprecipitated, and filtered, washed and dried to obtain 82.3 g of a pale yellow powder. As a result of HPLC analysis, it was found that the main component of the powder was a component corresponding to 91.0 area%. Also, this powder contained 0.7% by weight of resorcin. As a result of structural analysis, it was found that the main component in the powder was bis (3-hydroxyphenyl) succinate. [0041] The identification data of bis (3-hydroxyphenyl) succinate are as follows.
- the NMR ⁇ vector data is shown in Tables 3-1 and 3-2.
- Example 15 Using the composition prepared in Example 15 as a test conjugate, using a 2200 mL Banbury mixer, kneading and mixing according to the rubber compounding formulation shown in Table 4, an unvulcanized rubber composition was obtained. After the preparation, the bloom resistance, Mooney viscosity, adhesiveness immediately after compounding, and adhesiveness after leaving the compounded rubber were measured and evaluated by the following methods. Table 4 shows the results.
- the ML (1 + 4) of the unvulcanized rubber composition was measured at 130 ° C. in accordance with JIS K6300-2001. The results indicate that the lower the number, the better.
- Brass (Cu; 63% by mass; Zn; 37% by mass) steel cords (IX 5 structure, wire diameter 0.25mm) are arranged in parallel at 12.5mm intervals.
- the sample was immediately vulcanized under the conditions of 160 ° CXI for 5 minutes to produce a sample having a width of 12.5 mm.
- Initial adhesion was measured immediately after the vulcanization.
- the wet heat adhesiveness was measured after the vulcanization and after aging under the conditions of 70 ° C., 100% RH and 4 days of wet heat.
- An unvulcanized steel cord / rubber composite obtained by coating the steel cord with the rubber composition on both the upper and lower sides is left in a constant temperature and humidity chamber at 40 ° C. and 80% RH for 7 days, and then at 160 ° C. for 15 minutes. After vulcanization, the initial adhesiveness was measured and used as an index of adhesive stability.
- a rubber composition was prepared and evaluated in the same manner as in Reference Example except that the composition of the present invention was not used as a test compound. Table 4 shows the results.
- a rubber composition was prepared and evaluated in the same manner as in Reference Example except that 2 parts by mass of resorcin was added to the basic rubber compound as a test conjugate. Table 4 shows the results.
- a rubber composition was prepared and evaluated in the same manner as in Reference Example except that 2 parts by mass of RF resin was blended in the rubber base blend as a test conjugate. Table 4 shows the results.
- the RF resin was manufactured by the following method.
- a rubber composition was prepared and evaluated in the same manner as in the Example except that 2 parts by mass of the mixed polyester described in JP-A-7-118621 was mixed with the rubber base composition as a test conjugate. Table 4 shows the results.
- the mixed polyester was synthesized according to Example 1 described in the above patent.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES05720171.7T ES2558763T3 (es) | 2004-03-12 | 2005-03-07 | Compuesto y composición que contiene el mismo |
EP05720171.7A EP1724252B1 (en) | 2004-03-12 | 2005-03-07 | Compound and composition containing the same |
JP2005069771A JP4866009B2 (ja) | 2004-03-12 | 2005-03-11 | 化合物及びそれを含む組成物 |
US11/360,501 US7491840B2 (en) | 2004-03-12 | 2006-02-24 | Compound and composition containing the same |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004070791 | 2004-03-12 | ||
JP2004-070791 | 2004-03-12 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/360,501 Continuation US7491840B2 (en) | 2004-03-12 | 2006-02-24 | Compound and composition containing the same |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005087704A1 true WO2005087704A1 (ja) | 2005-09-22 |
Family
ID=34975500
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2005/003899 WO2005087704A1 (ja) | 2004-03-12 | 2005-03-07 | 化合物及びそれを含む組成物 |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP1724252B1 (ja) |
CN (1) | CN100445260C (ja) |
ES (1) | ES2558763T3 (ja) |
WO (1) | WO2005087704A1 (ja) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005290373A (ja) * | 2004-03-12 | 2005-10-20 | Bridgestone Corp | ゴム組成物及びそれを用いた空気入りタイヤ |
JP2007204668A (ja) * | 2006-02-03 | 2007-08-16 | Bridgestone Corp | 空気入りタイヤ |
JP2008231079A (ja) * | 2007-03-23 | 2008-10-02 | Mitsui Chemicals Inc | レゾルシン系ジエステル化合物の製造方法 |
JP2008239535A (ja) * | 2007-03-27 | 2008-10-09 | Mitsui Chemicals Inc | ジヒドロキシベンゼン誘導体の連続式製造方法 |
WO2009116156A1 (ja) | 2008-03-19 | 2009-09-24 | 三井化学株式会社 | ジヒドロキシベンゼン誘導体の製造方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2084347A5 (en) | 1970-03-09 | 1971-12-17 | Eastman Kodak Co | Fog inhibitors for silver halide emulsions - contg free acid groups |
JPS5290307A (en) | 1976-01-26 | 1977-07-29 | Canon Kk | Thermoodeveloping photoosensitive material for electrostatic printing master |
JPS58108527A (ja) | 1981-12-10 | 1983-06-28 | チバ・ガイギ−・ア−ゲ− | 写真材料 |
JPS63284291A (ja) * | 1987-05-18 | 1988-11-21 | Canon Inc | 高分子液晶組成物および液晶素子 |
EP0351832A2 (en) | 1988-07-20 | 1990-01-24 | Canon Kabushiki Kaisha | Nonlinear optical material and nonlinear optical device |
JPH06328429A (ja) | 1993-05-26 | 1994-11-29 | Sekisui Chem Co Ltd | セメント材料の原料供給装置 |
JPH07118621A (ja) | 1993-10-19 | 1995-05-09 | Sumitomo Chem Co Ltd | 接着剤およびそれのゴムへの適用 |
JPH07118621B2 (ja) | 1985-08-08 | 1995-12-18 | シ−メンス、アクチエンゲゼルシヤフト | パワ−トランジスタ装置 |
JP2001234140A (ja) | 2000-02-25 | 2001-08-28 | Bridgestone Corp | 接着性ゴム組成物 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP0292244B1 (en) * | 1987-05-18 | 1993-08-11 | Canon Kabushiki Kaisha | Polymeric liquid crystal composition and liquid crystal device |
EP1724302B1 (en) * | 2004-03-12 | 2011-07-20 | Bridgestone Corporation | Rubber composition and pneumatic tire using same |
US7823614B2 (en) * | 2004-12-08 | 2010-11-02 | Bridgestone Corporation | Pneumatic tire |
-
2005
- 2005-03-07 EP EP05720171.7A patent/EP1724252B1/en active Active
- 2005-03-07 CN CNB2005800078166A patent/CN100445260C/zh active Active
- 2005-03-07 ES ES05720171.7T patent/ES2558763T3/es active Active
- 2005-03-07 WO PCT/JP2005/003899 patent/WO2005087704A1/ja not_active Application Discontinuation
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
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FR2084347A5 (en) | 1970-03-09 | 1971-12-17 | Eastman Kodak Co | Fog inhibitors for silver halide emulsions - contg free acid groups |
JPS5290307A (en) | 1976-01-26 | 1977-07-29 | Canon Kk | Thermoodeveloping photoosensitive material for electrostatic printing master |
JPS58108527A (ja) | 1981-12-10 | 1983-06-28 | チバ・ガイギ−・ア−ゲ− | 写真材料 |
JPH07118621B2 (ja) | 1985-08-08 | 1995-12-18 | シ−メンス、アクチエンゲゼルシヤフト | パワ−トランジスタ装置 |
JPS63284291A (ja) * | 1987-05-18 | 1988-11-21 | Canon Inc | 高分子液晶組成物および液晶素子 |
EP0351832A2 (en) | 1988-07-20 | 1990-01-24 | Canon Kabushiki Kaisha | Nonlinear optical material and nonlinear optical device |
JPH06328429A (ja) | 1993-05-26 | 1994-11-29 | Sekisui Chem Co Ltd | セメント材料の原料供給装置 |
JPH07118621A (ja) | 1993-10-19 | 1995-05-09 | Sumitomo Chem Co Ltd | 接着剤およびそれのゴムへの適用 |
JP2001234140A (ja) | 2000-02-25 | 2001-08-28 | Bridgestone Corp | 接着性ゴム組成物 |
Non-Patent Citations (3)
Title |
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JIN J II ET AL., JOURNAL OF POLYMER SCIENCE, vol. 28, no. 4, 1990, pages 531 - 543 |
JIN J II ET AL: "Main chain thermotropic having flexible spacers - influence o ester group linking order between mesogenic unit and flexible spacer.", JOURNAL OF POLYMER SCIENCE, PART B: POLYMER PHYSICS, vol. 28, no. 4, 1990, pages 531 - 543, XP002989449 * |
See also references of EP1724252A4 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2005290373A (ja) * | 2004-03-12 | 2005-10-20 | Bridgestone Corp | ゴム組成物及びそれを用いた空気入りタイヤ |
JP2007204668A (ja) * | 2006-02-03 | 2007-08-16 | Bridgestone Corp | 空気入りタイヤ |
JP4637760B2 (ja) * | 2006-02-03 | 2011-02-23 | 株式会社ブリヂストン | 空気入りタイヤ |
JP2008231079A (ja) * | 2007-03-23 | 2008-10-02 | Mitsui Chemicals Inc | レゾルシン系ジエステル化合物の製造方法 |
JP2008239535A (ja) * | 2007-03-27 | 2008-10-09 | Mitsui Chemicals Inc | ジヒドロキシベンゼン誘導体の連続式製造方法 |
WO2009116156A1 (ja) | 2008-03-19 | 2009-09-24 | 三井化学株式会社 | ジヒドロキシベンゼン誘導体の製造方法 |
US8222446B2 (en) | 2008-03-19 | 2012-07-17 | Mitsui Chemicals, Inc. | Method for producing dihydroxybenzene derivative |
JP5362703B2 (ja) * | 2008-03-19 | 2013-12-11 | 三井化学株式会社 | ジヒドロキシベンゼン誘導体の製造方法 |
Also Published As
Publication number | Publication date |
---|---|
ES2558763T3 (es) | 2016-02-08 |
CN1930114A (zh) | 2007-03-14 |
CN100445260C (zh) | 2008-12-24 |
EP1724252B1 (en) | 2015-10-14 |
EP1724252A1 (en) | 2006-11-22 |
EP1724252A4 (en) | 2008-03-19 |
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