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WO2012020661A1 - Composition de résine époxy et durcissant - Google Patents

Composition de résine époxy et durcissant Download PDF

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Publication number
WO2012020661A1
WO2012020661A1 PCT/JP2011/067633 JP2011067633W WO2012020661A1 WO 2012020661 A1 WO2012020661 A1 WO 2012020661A1 JP 2011067633 W JP2011067633 W JP 2011067633W WO 2012020661 A1 WO2012020661 A1 WO 2012020661A1
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WO
WIPO (PCT)
Prior art keywords
epoxy resin
resin composition
weight
parts
epoxy
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
PCT/JP2011/067633
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English (en)
Japanese (ja)
Inventor
篤彦 片山
スレスタ・二ランジャン・クマール
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Nippon Steel Chemical and Materials Co Ltd
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Nippon Steel Chemical Co Ltd
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Priority to JP2012528644A priority Critical patent/JP5826751B2/ja
Publication of WO2012020661A1 publication Critical patent/WO2012020661A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/32—Epoxy compounds containing three or more epoxy groups
    • C08G59/38—Epoxy compounds containing three or more epoxy groups together with di-epoxy compounds
    • 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
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/027—Polycondensates containing more than one epoxy group per molecule obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/226—Mixtures of di-epoxy compounds
    • 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
    • C08G59/20—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 epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • 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
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1515—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend

Definitions

  • the present invention relates to an epoxy resin composition having a low viscosity and excellent workability, and an epoxy resin cured product having excellent heat resistance and mechanical properties obtained by curing the epoxy resin composition.
  • Epoxy resins are generally cured with various curing agents, resulting in cured products with excellent mechanical properties, water resistance, chemical resistance, heat resistance, electrical properties, etc., adhesives, paints, laminates, moldings It is used in a wide range of fields such as materials and casting materials.
  • bisphenol A type epoxy resin or bisphenol F type epoxy resin is mainly used as an epoxy resin in a liquid epoxy resin composition, but a reactive diluent may be added because the viscosity of the resin is relatively high. There were many.
  • reactive diluents butyl glycidyl ether, allyl glycidyl ether, and phenyl glycidyl ether have been representatively used.
  • Patent Document 2 proposes compounds having a cyclohexyl group, but the viscosity of these compounds is 240 cps to 3200 cps, which is higher than that of a conventional reactive diluent, and the function as a diluent is sufficient. Not.
  • polyepoxybenzenes are used as a reactive diluent. These are reactive diluents that can lower the viscosity of the entire composition, have the same reactivity as epichlorohydrin type epoxy, and do not lower the heat resistance and mechanical properties of the cured product.
  • epichlorohydrin type epoxy epichlorohydrin type epoxy
  • it is an aromatic compound, there is a problem that transparency and light resistance are slightly inferior to those of alicyclic compounds.
  • JP 7-97431 A Japanese Patent No. 3415047
  • the reactive diluent can reduce the viscosity of the entire composition, has the same reactivity as epichlorohydrin type epoxy, and does not reduce the heat resistance and mechanical properties of the cured product.
  • the appearance of is desired.
  • Epoxy resins having a low chlorine concentration are desired for use in electrical and electronic parts, and the emergence of reactive diluents having a low chlorine content is awaited. Further, in the optical component field, transparency and light resistance are also required.
  • the present inventors have intensively studied for a reactive diluent having a sufficiently low viscosity and not lowering the heat resistance and mechanical properties of the cured product and having a low chlorine content. It was found that the epoxy compound represented by) satisfies these requirements, and the present invention was completed.
  • the present invention includes an epoxy resin having a viscosity at 25 ° C. of 1000 mPa ⁇ s or more and polyepoxyethylcyclohexane represented by the following formula (1), and the content of the polyepoxyethylcyclohexane is the epoxy resin:
  • the present invention relates to an epoxy resin composition characterized by being 1 part by weight or more and 90 parts by weight or less with respect to 100 parts by weight.
  • E is an epoxy group
  • R is hydrogen, a vinyl group or an alkyl group
  • n represents an integer of 2 to 3
  • the present invention relates to a cured epoxy resin product obtained by blending and curing a curing agent in the above epoxy resin composition.
  • the present invention also relates to an epoxy resin composition characterized in that the polyepoxyethylcyclohexane is 1,2,4-triepoxyethylcyclohexane.
  • the present invention also relates to a reactive diluent for epoxy resin, characterized by comprising the above polyepoxyethylcyclohexane.
  • the epoxy resin composition of this invention contains the epoxy resin whose viscosity in 25 degreeC is 1000 mPa * s or more, and the polyepoxyethyl cyclohexane (henceforth an epoxy compound) represented by the said Formula (1).
  • the epoxy compound represented by the formula (1) one obtained by epoxidizing a corresponding vinyl compound with a peroxide can be used.
  • An epoxy compound in which a part of R is a vinyl group can be obtained by not epoxidizing all vinyl groups and reacting a part thereof when epoxidizing polyvinylcyclohexanes.
  • the epoxy compound obtained by this method has a feature that the chlorine content is low because epichlorohydrin is not used in the synthesis.
  • a peroxide used for epoxidation a normal peracid or an organic peroxide can be used.
  • this epoxy compound can be advantageously obtained by epoxidation by oxidation of polyvinylcyclohexanes (hereinafter also referred to as vinyl compounds). At this time, when the polyvinylcyclohexane is a stereoisomer mixture, this epoxy compound also becomes a stereoisomer mixture, but there is no problem.
  • R in the formula (1) is hydrogen, a vinyl group or an alkyl group. As the alkyl group, an alkyl group having 1 to 6 carbon atoms is preferable because of its low viscosity and particularly high effect as a diluent. Further, 6-n Rs may be the same or different.
  • all Rs are hydrogen, or 1 to 3 Rs are hydrogen, and the rest are vinyl groups or alkyl groups, particularly preferably derived from vinyl groups or alkyl groups.
  • the total number of carbon atoms to be performed is preferably 4 or less.
  • the epoxy resin having a viscosity at 25 ° C. of 1000 mPa ⁇ s or higher used in the epoxy resin composition of the present invention is not particularly limited as long as it satisfies the above viscosity.
  • epoxy resins such as cycloaliphatic epoxy resin, naphthalene novolac epoxy resin, diglycidyloxynaphthalene epoxy resin
  • bisphenol A type, bisphenol F type, bisphenol AD type, cresol novolac type glycidyl ether type epoxy resins and the like are particularly preferable in view of performance and economy.
  • Specific examples of these epoxy resins include bisphenol A-epichlorohydrin condensate epoxy resins such as EPICLON 850 (epoxy equivalent 188 g / eq) and EPICLON 1050 (epoxy equivalent 475 g / eq) manufactured by Dainippon Ink and Chemicals, Inc.
  • Noplac resin-epichlorohydrin such as EPICLON 30 N-670 (epoxy equivalent 210 g / eq), EPICLON N-670 (epoxy equivalent 210 g / eq), bisphenol F-epichlorohydrin condensate epoxy resin Condensate epoxy resin, Tetrabromobisphenol A-epichlorohydrin condensate epoxy resin such as EPICLON 152 (epoxy equivalent 360g / eq), EPICLON 430 (Epo Shi is equivalent 120 g / eq) aromatic glycidyl ether type epoxy resins such as glycidyl amine-type epoxy resins and the like.
  • the epoxy resin having a viscosity at 25 ° C. of less than 1000 mPa ⁇ s the effect of reducing the viscosity by the epoxy compound of the formula (1) is low.
  • the epoxy compound represented by the formula (1) used in the epoxy resin composition of the present invention has a function of reducing the viscosity of the epoxy resin composition.
  • the viscosity range of the epoxy compound is 10 to 500 mPa ⁇ s, it is preferable because of its excellent function of reducing the viscosity.
  • an epoxy resin having a viscosity at 25 ° C. of 1000 mPa ⁇ s or higher is a relatively general epoxy resin and has performance specific to the epoxy resin, but has a high viscosity.
  • an epoxy resin having a viscosity at 25 ° C. of 1000 mPa ⁇ s or more is also referred to as a high viscosity epoxy resin.
  • the addition amount of the epoxy compound represented by the formula (1) needs to be in the range of 1 to 90 parts by weight with respect to 100 parts by weight of the high viscosity epoxy resin.
  • the amount is preferably 5 to 80 parts by weight, more preferably 10 to 60 parts by weight.
  • the addition amount is less than 1 part by weight, the effect of reducing the viscosity is not sufficient, and when it exceeds 90 parts by weight, the physical properties of the original epoxy resin are reduced.
  • the epoxy compound represented by the formula (1) is excellent as an epoxy resin diluent.
  • the conventional epoxy resin diluent greatly reduces the Tg and strength of the cured product obtained by curing the epoxy resin composition, whereas the epoxy compound represented by the formula (1) used in the present invention has a low viscosity.
  • this epoxy compound has an alicyclic structure, there exists an effect that transparency is high.
  • the epoxy resin composition may be added with a flexible agent, a coupling agent, a flame retardant, a flame retardant aid, a colorant, a filler, etc. that are generally blended in the application field as necessary.
  • An agent may be added within a range not impairing the performance of the present invention.
  • a hardened epoxy resin is obtained by adding a curing agent to the epoxy resin composition of the present invention and curing it.
  • the curing agent used in the epoxy resin composition of the present invention may be a known curing agent as a general epoxy resin curing agent, for example, ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenetriamine.
  • Primary amines such as diethylaminopropylamine, metaphenylenediamine, p, p'-diaminodiphenylmethane, diaminodiphenylsulfone; secondary amines such as diethanolamine, N-methylethanolamine, bishydroxyethyldiethylenetriamine; triethylamine, piperidine, Tertiary amines such as benzyldimethylamine 2- (dimethylaminomethyl) phenol; phthalic anhydride, hexahydrophthalic anhydride, dodecenyl succinic anhydride, trimelli anhydride DOO acid, pyromellitic acid anhydride, include acid anhydrides such as HET acid, or these one or are formulated.
  • secondary amines such as diethanolamine, N-methylethanolamine, bishydroxyethyldiethylenetriamine; triethylamine, piperidine, Tertiary amines such as benzyldi
  • the mixing ratio of the epoxy resin and the curing agent is preferably in the range of 0.8 to 1.5 in terms of the equivalent ratio of the epoxy group and the functional group in the curing agent. Outside this range, unreacted epoxy groups or functional groups in the curing agent remain even after curing, and the physical properties of the cured product deteriorate.
  • the epoxy compound represented by Formula (1) is calculated as an epoxy resin.
  • epoxy resin composition of the present invention examples include paints, injection materials, cast products, composite materials such as CFRP, molded products, laminates and insulating materials such as printed boards, sealing materials for electrical and electronic parts, adhesion Agents, laminates, optical materials, FRP molded products, repair materials, flooring materials, road paving materials for civil engineering and the like.
  • Synthesis example 1 1,2,4-trivinylcyclohexane 80g (0.49mol), acetonitrile 323g (7.87mol), methanol 560g (17.5mol) and potassium carbonate 175g (1.27mol), thermometer, cooling tube, nitrogen inlet tube, stirring blade Into a 2 L five-necked separable flask. After purging with nitrogen, the internal temperature was adjusted to 20 to 25 ° C., and 630 g (5.55 mol) of 30% hydrogen peroxide was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was carried out for 5 hours while keeping the internal temperature between 25-45 ° C.
  • the remaining peroxide in the reaction solution was decomposed using 186.6 g (0.15 mol) of a 10% aqueous sodium sulfite solution. 600 g (6.51 mol) of toluene was added, and the aqueous layer and the organic layer were separated. After separation, the organic layer was washed with water three times and dried using sodium sulfate. After evaporation of the organic layer (toluene layer) using an evaporator, the mixture was purified and separated by distillation under reduced pressure using an epoxy mixture (including monoepoxy, diepoxy, and triepoxy).
  • an epoxy mixture including monoepoxy, diepoxy, and triepoxy
  • TEpCH 1,2,4-triepoxyethyl hexane
  • the viscosity of the resin composition at 25 ° C. was measured with a B-type viscometer.
  • Jamaicacid MH-700 manufactured by Shin Nippon Chemical Co., Ltd. was added to the epoxy resin composition so that the equivalent ratio was 0.9 and mixed uniformly, then poured into a mold, 120 ° C., 1 hour, and then 150 C.
  • test piece for bending test having a length of 125 mm.times.width of 13 mm.times.thickness of 3 mm and a glass transition point test piece having a diameter of 5 mm.times.3 mm of thickness were prepared.
  • the bending test specified in JIS K7171 was performed at 25 ° C., and the bending strength was determined from the maximum strength. Also, the flexural modulus was determined from the initial slope of the strain-stress curve.
  • Comparative Examples 4-6 10 parts by weight, 25 parts by weight or 50 parts by weight of butyl glycidyl ether (BGE; manufactured by Tokyo Chemical Industry Co., Ltd.) is added to 100 parts by weight of the bisphenol A type epoxy resin (YD-128), and mixed to form an epoxy resin composition. I got a thing. To this epoxy resin composition, Jamaicacid MH-700 was added so as to have an equivalent ratio of 0.9 and mixed uniformly, and then the test piece for bending test and glass transition point measurement were performed in the same manner as in Examples 1 to 3. Test pieces were prepared and bending strength, flexural modulus and glass transition point were determined.
  • BGE butyl glycidyl ether
  • Example 4 50 parts by weight of 1,2,4-triepoxyethylcyclohexane (TEpCH) obtained in Synthesis Example 1 is added to 100 parts by weight of bisphenol F type epoxy resin (YD-170; manufactured by Tohto Kasei Co., Ltd.) and mixed. An epoxy resin composition was obtained. The viscosity of the resin composition at 25 ° C. was measured with a B-type viscometer. After adding Jamaicacid MH-700 to the epoxy resin composition so that the equivalent ratio becomes 0.9 and mixing it uniformly, in the same manner as in Examples 1 to 3, a test piece for bending test and a glass transition point measurement A test piece was prepared, and bending strength, flexural modulus and glass transition point were determined.
  • TEpCH 1,2,4-triepoxyethylcyclohexane
  • Example 5 50 parts by weight of 1,2,4-triepoxyethylcyclohexane (TEpCH) obtained in Synthesis Example 1 is added to and mixed with 100 parts by weight of phenol novolac type epoxy resin (YDPN-638; manufactured by Toto Kasei Co., Ltd.). An epoxy resin composition was obtained. To this epoxy resin composition, Jamaicacid MH-700 was added so as to have an equivalent ratio of 0.9 and mixed uniformly, and then the test piece for bending test and glass transition point measurement were performed in the same manner as in Examples 1 to 3. Test pieces were prepared and bending strength, flexural modulus and glass transition point were determined.
  • phenol novolac type epoxy resin YDPN-638; manufactured by Toto Kasei Co., Ltd.
  • Table 1 shows the composition and viscosity of the resin compositions of Examples 1 to 5 and Comparative Examples 1 to 6, and the measured physical properties of the cured products.
  • the compound addition amount is a compounding amount of the epoxy compound with respect to 100 parts by weight of the epoxy resin.
  • the viscosity was measured at 25 ° C.
  • a viscosity is a viscosity of the epoxy resin composition before mix
  • Comparative Example 7 After adding Jamaicacid MH-700 to bisphenol A type epoxy resin (YD-128) so that the equivalent ratio becomes 0.9 and mixing it uniformly, a test piece for bending test is carried out in the same manner as in Examples 1 to 3. And the test piece for glass transition point measurement was produced, and bending strength, a bending elastic modulus, and the glass transition point were calculated
  • Comparative Example 8 After adding Jamaicacid MH-700 to bisphenol F type epoxy resin (YD-170) so that the equivalent ratio becomes 0.9 and mixing it uniformly, a test piece for bending test was carried out in the same manner as in Examples 1 to 3. And the test piece for glass transition point measurement was produced, and bending strength, a bending elastic modulus, and the glass transition point were calculated
  • Comparative Example 9 After adding Rikacid MH-700 to a phenol novolac type epoxy resin (YDPN-638) so that the equivalent ratio becomes 0.9 and mixing it uniformly, a test piece for bending test was carried out in the same manner as in Examples 1 to 3. And the test piece for glass transition point measurement was produced, and bending strength, a bending elastic modulus, and the glass transition point were calculated
  • Table 2 shows the viscosity at 25 ° C. of the epoxy resins used in Comparative Examples 7 to 9 and the measured physical properties of the cured products. The compound addition amount is zero.
  • the hydrolyzable chlorine content was analyzed by the following method. That is, about 1 g of a sample is put in a 100 mL Erlenmeyer flask and accurately weighed to a unit of 1 mg. 30 mL of dioxane was added and dissolved completely using an ultrasonic cleaner. After correctly adding 5 mL of 1N potassium hydroxide / ethanol solution and shaking well, boiling stones were added and a condenser tube was attached. The mixture was heated to about 180 ° C. and refluxed. The reflux time was correctly set to 30 minutes after boiling started. After cooling to room temperature, the cooling tube was washed with 5 mL of methanol, and the washing solution was added to the sample solution.
  • the Erlenmeyer flask was removed from the condenser, and the sample solution was transferred to a 200 mL beaker. The flask was washed three times with 50 mL of 80% acetone water, and the washing solution was added to the sample solution. 5 mL of N / 400 sodium chloride solution was added correctly and a rotator was added. After adding 3 mL of acetic acid and stirring for 2 minutes, potentiometric titration was performed using the N / 100 silver nitrate solution under the following conditions. A blank test was performed by the same operation as above. The hydrolyzable chlorine concentration was determined by the following formula.
  • Hydrolyzable chlorine (%) F ⁇ (V ⁇ B) ⁇ 0.0355 / S F; Factor of N / 100 silver nitrate solution V; Amount of N / 100 silver nitrate solution required for titration of sample B; Amount of N / 100 silver nitrate solution required for titration of blank test S; Amount of sample (g)
  • Example 6 Hydrogenated bisphenol A glycidyl ether type epoxy resin (Licar Resin HBE-100; manufactured by Shin Nippon Chemical Co., Ltd.) 100 parts by weight of viscosity (1950 cps 25 ° C.) 1,2,4-triepoxyethylcyclohexane obtained in Synthesis Example 1 ( 50 parts by weight of TEpCH) was added and mixed to obtain an epoxy resin composition, which was then mixed uniformly with an equivalent ratio of 0.9 to an equivalent ratio of 0.9, followed by vacuum. Degassing and curing in a mold at 100 ° C. for 4 hours and further at 140 ° C. for 12 hours to produce resin plates having a thickness of 1 mm and 4 mm. Measurements of UV resistance and initial heat resistance were made, and bending test specimens and glass transition point measurement specimens were prepared in the same manner as in Examples 1 to 3, and bending strength and flexural modulus were measured. And the glass transition point .
  • Licar Resin HBE-100 manufactured by Shin N
  • Comparative Example 10 50 parts by weight of diepoxyethylbenzene (DEpEB) obtained in Synthesis Example 2 is added to 100 parts by weight of hydrogenated bisphenol A glycidyl ether type epoxy resin (Licar Resin HBE-100; manufactured by Shin Nippon Chemical Co., Ltd. at 1950 cps 25 ° C). The mixture was mixed to obtain an epoxy resin composition, which was then mixed uniformly with an equivalent ratio of 0.9 to 0.9, and then vacuum degassed to remove the inside of the mold. Thus, a resin plate having a thickness of 1 mm and 4 mm was prepared by curing at 100 ° C. for 4 hours and further at 140 ° C. Using this test piece, the initial transmittance and UV resistance of the cured product were measured. The heat resistance was measured, and a bending test specimen and a glass transition point measurement specimen were prepared in the same manner as in Examples 1 to 3, and the bending strength, flexural modulus, and glass transition point were determined. .
  • DEpEB diepoxy
  • Example 6 the initial transmittance, UV resistance, and initial heat resistance of the cured product were measured by the following methods.
  • Table 3 shows the blending composition, viscosity, physical properties of the cured product, initial transmittance of the cured product, UV resistance, and initial heat resistance of Example 6 and Comparative Example 10.
  • the compound addition amount is a compounding amount of the epoxy compound with respect to 100 parts by weight of the epoxy resin.
  • the cured product containing TEpCH is excellent in initial transmittance, UV resistance, and initial heat resistance. That is, it is excellent in transparency and light resistance and is useful as an optical resin.
  • the epoxy resin composition of the present invention has low viscosity and excellent workability, and the cured epoxy resin obtained by curing it has excellent heat resistance, mechanical properties, transparency, and light resistance.

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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)
  • Epoxy Resins (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne une composition de résine époxy mélangée à une petite quantité de diluant réactif et se présentant ainsi sous la forme d'une solution de faible viscosité, les propriétés mécaniques et la résistance à la chaleur de ladite composition de résine époxy contenant ledit diluant réactif étant meilleures que celles de compositions de résine époxy ne contenant pas le diluant réactif. Une composition de résine époxy liquide de faible viscosité possédant une excellente aptitude au façonnage peut être préparée à partir d'une composition de résine époxy contenant de la résine époxy et du poly(époxy-éthylcyclohexane), la quantité de poly(époxy-éthylcyclohexane) ajoutée étant de 1 pour 90 parties en poids, pour 100 parties en poids de résine époxy. Selon l'invention, il est possible d'obtenir un matériau durci à base de résine époxy possédant d'excellentes propriétés mécaniques et de résistance à la chaleur en mélangeant un durcissant avec ladite résine époxy, puis en faisant durcir ledit durcissant.
PCT/JP2011/067633 2010-08-09 2011-08-02 Composition de résine époxy et durcissant Ceased WO2012020661A1 (fr)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014066717A1 (fr) * 2012-10-26 2014-05-01 Dow Global Technologies Llc Composés époxy inédits : dérivés de 1,3-dioxiranylcyclopentane
WO2014066718A1 (fr) * 2012-10-26 2014-05-01 Dow Global Technologies Llc Compositions durcissables contenant des composés époxy à base de 1,3-dioxiranylcyclopentane et résines thermodurcissables préparées à partir de celles-ci
JP2014094937A (ja) * 2012-10-11 2014-05-22 Mitsubishi Chemicals Corp 新規エポキシ化合物
JP2018165359A (ja) * 2017-03-28 2018-10-25 積水化学工業株式会社 樹脂組成物及びインダクタ
KR20220104959A (ko) * 2021-01-19 2022-07-26 한국화학연구원 삼관능성 지환족 에폭시 화합물을 포함하는 에폭시 수지 제조용 조성물 및 이를 이용한 경화물
CN118027606A (zh) * 2024-02-02 2024-05-14 重庆克那维环保科技有限公司 一种管道非开挖用修复材料及其制备方法

Citations (3)

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