CN101186796A - Method for preparing epoxy resin adhesive - Google Patents
Method for preparing epoxy resin adhesive Download PDFInfo
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- CN101186796A CN101186796A CNA2007101718902A CN200710171890A CN101186796A CN 101186796 A CN101186796 A CN 101186796A CN A2007101718902 A CNA2007101718902 A CN A2007101718902A CN 200710171890 A CN200710171890 A CN 200710171890A CN 101186796 A CN101186796 A CN 101186796A
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Abstract
The invention discloses a process for preparing epoxy resin adhesive. Epoxy phenyl silicone oil(PEPDMS) is employed as toughening modifiers of the epoxy-resin adhesive, the mixing compatibility of organic silicon resin and epoxy resin is improved by introducing phenyl group to the molecular structure of the epoxy silicone oil, simultaneously, the impact ductility and bending intensity of cured resin can be increased owing to the mutual effects of soft Si-O-Si chain and the rigid phenyl group, thereby the invention has toughening and strengthening effects, and the invention has the advantages of sound heat-resistance and electric insulation. The beginning heat decomposition temperature is more than 400 DEG C, volume resistivity is more than 10 17 omega*cm at room temperature, the medium loss is less than 2% at room temperature and at the temperature of 155 DEG C, and the invention is in particular adaptable for casting and the packaging of electronic materials and the manufacture of electric insulation materials.
Description
Technical field
The present invention relates to a kind of preparation method's of tackiness agent, particularly a kind of epoxyn preparation method.
Background technology
Resins, epoxy has advantages such as good mechanical property, electric property, chemical proofing, adhesive property, and be widely used in the matrix of coating, tackiness agent, electric insulated with material and advanced composite material, this year, electric insulating material develops to high performance, this just needs material to have higher performance, as high tenacity, inner low stressization, heat-resisting, moisture-proof etc., and deficiencies such as the most matter of epoxy resin cured product is crisp, thermotolerance is not high, the easy moisture absorption.
The method of epoxy resin roughening mainly contains at present: rubber elastomer is toughness reinforcing, thermoplastic resin is toughness reinforcing, thermotropic liquid crystal is toughness reinforcing, interpenetrating(polymer)networks are toughness reinforcing, organosilicon is toughness reinforcing etc., and every kind of method has relative merits.Wherein organosilicon polymer is owing to contain a large amount of flexible Si-O-Si chains in the molecular structure, have low surface energy, heat-resisting, advantages such as oxytolerant aging, hydrophobicity is good, excellent insulation performance, can remedy the deficiency of Resins, epoxy, can satisfy the needs of high performance composite development, but both consistencies are very poor.The functional polysiloxane modified epoxy especially contains the polyoxy alkane of epoxy group(ing), owing to the consistency of itself and Resins, epoxy better receives much concern, as patent CN 1747985A, CN1189847A, CN1932149A, CN1875071A, but used epoxy group(ing) polysiloxane is the low polymerization degree molecule mostly, still there are problems such as consistency is bad in high molecular weight epoxy silicone oil and Resins, epoxy, even still have phenomenon of phase separation to take place after pre-reaction is solidified, and cause system thermotolerance, mechanical property to descend.The method of the silicon oil modified epoxy resin composite material of epoxy group(ing) is disclosed among the patent CN1796455A, mainly be by epoxy group(ing) silicone oil and the pre-reaction of amine curing agent elder generation, mix with Resins, epoxy again, but performance can sharply descend after addition increased to certain proportion, had had a strong impact on the operability of application art.
Summary of the invention:
The object of the invention is to improve flexural strength decline and the relatively poor shortcoming of electrical property when consistency is bad, toughness reinforcing in the silicon oil modified epoxyn process of epoxy group(ing), realize good consistency, do not reduce flexural strength, thermotolerance and insulating property in the time of toughness reinforcing.
The preparation method of a kind of epoxyn of the present invention is as follows, below all represents with weight part:
With 100 parts of Resins, epoxy 80-100 ℃ of following fusion, the final vacuum de-bubbled that stirs 0.5-1.0 hour, be warming up to 100-160 ℃ and add curing catalyst 0.01-10 part, be stirred to the curing catalyst fusion evenly, be cooled to 80-100 ℃ and add 0-100 part filler, add 0.1-200 part epoxy and phenyl silicone oil, 10-150 part solidifying agent after being uniformly dispersed again, stirring obtains a kind of epoxyn.
The Resins, epoxy that the present invention uses is 1 as the mixture of bisphenol A epoxide resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio: 2-3: 1; The mixture of bisphenol A epoxide resin, cycloaliphatic epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 4-2: 1: 1; The mixture of bisphenol A epoxide resin, hydrogenated bisphenol A epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 4-2: 1: 1; The mixture of hydrogenated bisphenol A epoxy resin, cycloaliphatic epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 2-2: 1: 1; The mixture of bisphenol A epoxide resin, hydrogenated bisphenol A epoxy resin, cycloaliphatic epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 1: 6-3: 3: 1: 1; Wherein the epoxy equivalent (weight) of bisphenol A epoxide resin is 150-2000g/mol, the epoxy equivalent (weight) of linear phenol formaldehyde (PF) Resins, epoxy is 180-250g/mol, the epoxy equivalent (weight) of hydrogenated bisphenol A epoxy resin is 200-1100g/mol, the epoxy equivalent (weight) of linear phenol formaldehyde (PF) Resins, epoxy is 180-250g/mol, cycloaliphatic epoxy resin is 3,4-epoxy-cyclohexane formic acid-3 ', 4 '-epoxy-cyclohexane methyl esters, its epoxy equivalent (weight) is 131-143g/mol or 3,4-epoxy group(ing)-6-methylcyclohexane formic acid-3 ', 4 '-epoxy group(ing)-6-methylcyclohexane methyl esters, its epoxy equivalent (weight) is 152-156g/mol.
The structural formula of the epoxy and phenyl silicone oil that the present invention uses is:
Or
M=1-100 wherein, n=1-100.
The solidifying agent that the present invention uses is MALEIC ANHYDRIDE, methylhexahydrophthalic anhydride, Tetra Hydro Phthalic Anhydride, methyl carbic anhydride, diaminodiphenyl-methane or diamino diphenyl sulfone.
The curing catalyst that the present invention uses is aluminium acetylacetonate, acetylacetone copper, methyl ethyl diketone neodymium, 2,4,6-three (dimethylamino methyl) phenol or Bian Ji dimethylamine.
The filler that the present invention uses is SiO
2, Al
2O
3Or TiO
2, particle diameter is 1nm-100mm.
The preparation method of a kind of epoxyn of the present invention, utilize the plasticized modifier of epoxy and phenyl silicone oil as epoxyn, by in epoxy group(ing) silicone oil molecular structure, introducing phenyl group, improved the consistency of silicone resin and Resins, epoxy, simultaneously because the flexible Si-O-Si chain and the acting in conjunction of inflexible phenyl group, can improve the impelling strength and the flexural strength of cured article simultaneously, has toughness reinforcing enhanced effect, and have good thermotolerance and electrical insulation properties, its initial heat decomposition temperature is greater than 400 ℃ of (TGA measurement, N
2In 20 ℃ of temperature rise rates/min), room temperature lower volume resistivity is greater than 10
17Ω .cm, room temperature and 155 ℃ of following dielectric losses are specially adapted to the cast encapsulation of electronic material and the manufacturing of insulating material all less than 2%.
Embodiment:
Following enforcement is to further specify of the present invention, but not to limiting the scope of the invention.、
Shock strength, flexural strength, volume specific resistance and dielectric loss are tested by GB/T2571-1995, GB/T 2570-1995, GB/T 1410-2006 and GB/T 1409-1988 respectively in following examples, and the TGA thermal weight loss is tested at N
2Carry out under the condition that middle temperature rise rate is 20 ℃/min.
Embodiment 1:
With 25g bisphenol A epoxide resin (trade mark DER331, DOW Chemicals, epoxy equivalent (weight) are 182-192g/mol), 25g bisphenol A epoxide resin (trade mark 1050, Wuxi Di Aisheng, epoxy equivalent (weight) 450-500 are g/mol); With the linear phenol formaldehyde (PF) Resins, epoxy of 50g (trade mark F-44, Shanghai is striven sharp, epoxy equivalent (weight) is 205-213g/mol) 80～100 ℃ of following fusions, the final vacuum de-bubbled that stirs 0.5-1.0 hour is warming up to 140 ℃ and adds the 0.3g aluminium acetylacetonates, be stirred to aluminium acetylacetonate fusion evenly after, (structural formula is a to be cooled to 100 ℃ of adding 30g methylhexahydrophthalic anhydrides and 10g epoxy and phenyl silicone oil, m=20-25, n=23-26), stirring obtains the 140g epoxyn.Mix with curing front and back mixture and all be transparence, do not have the generation that is separated.Shock strength 15KJ/m
2, improve 40% than pure epoxy system; Flexural strength 107MPa improves 7% than pure epoxy system; Room temperature lower volume resistivity 4 * 10
17Ω .cm, dielectric loss 0.3%; 155 ℃ of following dielectric losses 1.1%; 430 ℃ of (N of the initial heat decomposition temperature of TGA
2, 20 ℃ of temperature rise rates/min).
Embodiment 2:
With 50g bisphenol A epoxide resin (trade mark DER331, DOW Chemicals, epoxy equivalent (weight) 182-192 are g/mol), 25g cycloaliphatic epoxy resin (trade mark ERL4221, Union Carbide,, epoxy equivalent (weight) is 131-143g/mol); With the linear phenol formaldehyde (PF) Resins, epoxy of 25g (trade mark F-44, Shanghai is striven sharp, epoxy equivalent (weight) is 205-213g/mol) 80～100 ℃ of following fusions, the final vacuum de-bubbled that stirs 0.5-1.0 hour is warming up to about 140 ℃ and adds the 0.25g aluminium acetylacetonate, be stirred to aluminium acetylacetonate fusion evenly after, be cooled to 100 ℃ and add 35g methylhexahydrophthalic anhydride and 10g epoxy and phenyl silicone oil (structural formula such as b, m=21-25 n=24-28), obtains the 145g epoxyn.Mix with curing front and back mixture and all be transparence, do not have the generation that is separated.Shock strength 13KJ/m
2, improve 34% than pure epoxy system; Flexural strength 114MPa improves 10% than pure epoxy system; Room temperature lower volume resistivity 6 * 10
17Ω .cm, dielectric loss 0.25%; 155 ℃ of following dielectric losses 1.5%; 507 ℃ of (N of the initial heat decomposition temperature of TGA
2, 20 ℃ of temperature rise rates/min).
Embodiment 3:
With the 25g bisphenol A epoxide resin (trade mark DER331, DOW Chemicals,, epoxy equivalent (weight) is 182-192g/mol), the 25g bisphenol A epoxide resin (trade mark 1050, Wuxi Di Aisheng,, epoxy equivalent (weight) is 450-500g/mol); With the linear phenol formaldehyde (PF) Resins, epoxy of 50g (trade mark F-44, Shanghai is striven sharp, epoxy equivalent (weight) is 205-213g/mol) 80～100 ℃ of following fusions, the final vacuum de-bubbled that stirs 0.5-1.0 hour, be warming up to and add the 0.3g aluminium acetylacetonate about 140 ℃, after being stirred to aluminium acetylacetonate fusion evenly, cool to that to add the 5g particle diameter about 100 ℃ be SiO about 15nm
2, being uniformly dispersed, (structural formula such as a, m=30-33 n=35-37), obtain the 147g epoxyn for back adding 32g methylhexahydrophthalic anhydride and 10g epoxy and phenyl silicone oil.Mix with curing front and back mixture and all be transparence, do not have the generation that is separated.Shock strength 18KJ/m
2, improve 46% than pure epoxy system; Flexural strength 126MPa improves 17% than pure epoxy system; Room temperature lower volume resistivity 8 * 10
17Ω .cm, dielectric loss 0.28%; 155 ℃ of following dielectric losses 1.9%; 475 ℃ of (N of the initial heat decomposition temperature of TGA
2, 20 ℃ of temperature rise rates/min).
Claims (6)
1. the preparation method of an epoxyn is characterized in that its preparation method is as follows, below is weight part and represents:
With 100 parts of Resins, epoxy 80-100 ℃ of following fusion, the final vacuum de-bubbled that stirs 0.5-1.0 hour, be warming up to 100-160 ℃ and add curing catalyst 0.01-10 part, be stirred to the curing catalyst fusion evenly, be cooled to and add 0-100 part filler below 100 ℃, add 0.1-200 part epoxy and phenyl silicone oil, 10-150 part solidifying agent after being uniformly dispersed again, stirring obtains a kind of epoxyn.
2. the preparation method of a kind of epoxyn according to claim 1 is characterized in that Resins, epoxy is the mixture of bisphenol A epoxide resin and linear phenol formaldehyde (PF) Resins, epoxy, and weight ratio is 1: 2-3: 1; The mixture of bisphenol A epoxide resin, cycloaliphatic epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 4-2: 1: 1; The mixture of bisphenol A epoxide resin, hydrogenated bisphenol A epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 4-2: 1: 1; The mixture of hydrogenated bisphenol A epoxy resin, cycloaliphatic epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 2-2: 1: 1; The mixture of bisphenol A epoxide resin, hydrogenated bisphenol A epoxy resin, cycloaliphatic epoxy resin and linear phenol formaldehyde (PF) Resins, epoxy, weight ratio are 1: 1: 1: 6-3: 3: 1: 1; Wherein the epoxy equivalent (weight) of bisphenol A epoxide resin is 150-2000g/mol, and the epoxy equivalent (weight) of linear phenol formaldehyde (PF) Resins, epoxy is 180-250g/mol; The epoxy equivalent (weight) of hydrogenated bisphenol A epoxy resin is 200-1100g/mol; Cycloaliphatic epoxy resin is 3,4-epoxy-cyclohexane formic acid-3 ', 4 '-epoxy-cyclohexane methyl esters, epoxy equivalent (weight) is 131-143g/mol or 3,4-epoxy group(ing)-6-methylcyclohexane formic acid-3 ', 4 '-epoxy group(ing)-6-methylcyclohexane methyl esters, epoxy equivalent (weight) is 152-156g/mol.
3. the preparation method of a kind of epoxyn according to claim 1 is characterized in that the structural formula of epoxy and phenyl silicone oil is:
M=1-100 wherein, n=1-100.
4. the preparation method of a kind of epoxyn according to claim 1 is characterized in that solidifying agent is MALEIC ANHYDRIDE, methylhexahydrophthalic anhydride, Tetra Hydro Phthalic Anhydride, methyl carbic anhydride, diaminodiphenyl-methane or diamino diphenyl sulfone.
5. the preparation method of a kind of epoxyn according to claim 1 is characterized in that promotor is aluminium acetylacetonate, acetylacetone copper, methyl ethyl diketone neodymium, 2,4,6-three (dimethylamino methyl) phenol or Bian Ji dimethylamine.
6. the preparation method of a kind of epoxyn according to claim 1 is characterized in that filler is SiO
2, Al
2O
3Or TiO
2, its particle diameter is 1nm-100mm.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101718902A CN101186796A (en) | 2007-12-06 | 2007-12-06 | Method for preparing epoxy resin adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007101718902A CN101186796A (en) | 2007-12-06 | 2007-12-06 | Method for preparing epoxy resin adhesive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN101186796A true CN101186796A (en) | 2008-05-28 |
Family
ID=39479419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNA2007101718902A Pending CN101186796A (en) | 2007-12-06 | 2007-12-06 | Method for preparing epoxy resin adhesive |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101186796A (en) |
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| CN101880515A (en) * | 2010-06-28 | 2010-11-10 | 深圳市库泰克电子材料技术有限公司 | High-reliability and low-viscosity underfill |
| CN102086365A (en) * | 2010-12-27 | 2011-06-08 | 东莞市腾威电子材料技术有限公司 | Adhesive, preparation method and application in integrated circuit board embedment thereof |
| CN102206322A (en) * | 2010-03-30 | 2011-10-05 | 江苏力宝建材工业有限公司 | Epoxy-modified organic silicone resin for manufacturing composite glue, and processing technology thereof |
| CN102286261A (en) * | 2011-07-14 | 2011-12-21 | 上海景涵实业有限公司 | Epoxy functional organic silicon conductive adhesive for amino curing system for light emitting diode (LED) |
| CN102642263A (en) * | 2012-05-11 | 2012-08-22 | 中国航空动力机械研究所 | Vacuum casting process method of photoelastic model |
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| CN102206322B (en) * | 2010-03-30 | 2012-09-26 | 江苏力宝建材工业有限公司 | Epoxy-modified organic silicone resin for manufacturing composite glue, and processing technology thereof |
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| CN102286261A (en) * | 2011-07-14 | 2011-12-21 | 上海景涵实业有限公司 | Epoxy functional organic silicon conductive adhesive for amino curing system for light emitting diode (LED) |
| CN102286261B (en) * | 2011-07-14 | 2014-07-09 | 上海本诺电子材料有限公司 | Epoxy functional organic silicon conductive adhesive for amino curing system for light emitting diode (LED) |
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| CN108342175A (en) * | 2018-02-07 | 2018-07-31 | 滕凤琴 | A kind of epoxyn and preparation method thereof |
| CN109385241A (en) * | 2018-10-11 | 2019-02-26 | 中国科学院长春应用化学研究所 | A kind of silicon Graft Epoxy Resin adhesive |
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| CN113831877A (en) * | 2021-09-27 | 2021-12-24 | 湖北晟特新材料有限公司 | Modified epoxy resin adhesive and application thereof in hard mica plate |
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