CN109749359A - one-component epoxy resin composition - Google Patents
one-component epoxy resin composition Download PDFInfo
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- CN109749359A CN109749359A CN201711065813.9A CN201711065813A CN109749359A CN 109749359 A CN109749359 A CN 109749359A CN 201711065813 A CN201711065813 A CN 201711065813A CN 109749359 A CN109749359 A CN 109749359A
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Abstract
A kind of one-component epoxy resin composition, latent curing agent, liquid phenolic resin and epoxy-silane copolymer compound including liquid-state epoxy resin, for solidifying the liquid-state epoxy resin.
Description
Technical field
The present invention relates to a kind of one-component epoxy resin composition, in particular to a kind of single group using latent curing agent
Divide composition epoxy resin.
Background technique
During epoxy resin has been used for being widely applied, such as coating material, electricity and electrical insulating material and adhesive.Especially
It is that in recent years, in order to improve the productivity in electronic material application, it is necessary to have the lists of excellent curing properties and storage stability
Component epoxy composition.
Summary of the invention
In view of this, using latent curing agent, having preferable it is necessary to provide a kind of one-component epoxy resin composition
Curing properties and storage stability.
A kind of one-component epoxy resin composition, including liquid-state epoxy resin, for solidifying the liquid-state epoxy resin
Latent curing agent, liquid phenolic resin and epoxy-silane copolymer compound.
Compared with the prior art, the viscosity of the one-component epoxy resin composition of the technical program is lower, solidification temperature
Spend it is relatively low, it is superior in terms of machinability and storage characteristics, and there is long working life.
Detailed description of the invention
Nothing
Main element symbol description
Nothing
The present invention will be further illustrated in following specific embodiment.
Specific embodiment
Technical solution of the present invention embodiment provides a kind of one-component epoxy resin composition, it includes:
(a) liquid-state epoxy resin；
(b) latent curing agent；
(c) liquid phenolic resin；And
(d) epoxy-silane copolymer compound.
The liquid-state epoxy resin of said components (a) is at room temperature or be liquid at 25 DEG C.The liquid-state epoxy resin can be with
It is made of a kind of epoxy resin, or can be the mixture of two or more epoxy resin.
In one embodiment, the liquid-state epoxy resin includes being selected from bisphenol A type epoxy resin, bisphenol F type epoxy
At least one of resin, catechol and resorcinol.
As the latent curing agent of the component (b), one or more latent curing agents can be selected from usually commercially available
Latent curing agent and use.In particular, amido latent curing agent is preferred, the reality of the amido latent curing agent
Example includes the hitherto known amine compounds and modified amine such as amine adduct with latency.The modified amine includes core
Shell mould curing agent, the modified product that wherein surface of the core of amine compounds (or amine adduct) is surrounded by amine (are transformed into adduct
Surface) shell and masterbatch type curing agent, wherein the hud typed curing agent is in the state that mixes with epoxy resin.
The example of the amine compounds with latency includes aromatic primary amine such as diaminodiphenylmethane and diamino hexichol
Sulfone；Imidazoles such as 2- heptadecyl imidazole, 1- cyanoethyl -2- undecyl imidazole trimellitate, 2,4- diamino -6- [2-
Methylimidazolyl-(1)]-ethyl-S- triazine, 1- dodecyl -2- methyl-3-benzyl imidazole chloride, 2- phenylimidazole
Isocyanuric acid ester and 2 phenyl 4 methyl 5 hydroxy methylimidazole；Borontrifluoride boron-amine complex；Such as double cyanogen of cyanoguanidine derivative
Amine, OTBG o tolylbiguanide and α -2,5- methyl biguanides；Organic acid hydrazides such as amber acid dihydrazide and adipic dihydrazide；Diamino
Maleic dintrile and its derivative；With melamine derivative such as melamine and diallyl melamine.
In general, the latent curing agent refers to powder solid latent curing agent.
It is anti-with epoxide, isocyanate compound and/or a carbamide compound that the amine adduct is amine compounds
Answer product.
Be used to prepare amine adduct amine compounds can be intramolecular have can be with epoxy group, isocyanate group or urea
Compound, which carries out one or more reactive hydrogens of addition reaction and intramolecular, to be had selected from primary amino group, secondary amino group or tertiary amino extremely
The compound of a few substituent group.The example of this amine compound includes amine compounds such as diethylenetriamines, triethylene four
Amine, n-propylamine, 2- hydroxyethylamino propylamine, cyclohexylamine, dimethylamino propylamine, dibutyl amino propyl amine, dimethylaminoethyl
Amine, diethylaminoethylamiand and N methyl piperazine；Intramolecular includes the primary amine or secondary amine of tertiary amino, including imidazolium compounds such as 2-
Methylimidazole, 2- ethyl imidazol(e), 2-ethyl-4-methylimidazole and 2- phenylimidazole；Intramolecular includes alcohol, phenol, the sulphur of tertiary amino
Alcohol, carboxylic acid and hydrazides, such as 2-dimethylaminoethanol, 1- methyl -2-dimethylaminoethanol, 1- Phenoxymethyl -2- dimethylamino second
Alcohol, 2-diethylaminoethanol, 1- butoxymethyl -2-dimethylaminoethanol, 1- (2- hydroxyl -3- phenoxy propyl) -2- methyl
Imidazoles, 1- (2- hydroxyl -3- phenoxy propyl) -2-ethyl-4-methylimidazole, 1- (2- hydroxyl -3- butoxypropyl) -2- methyl
Imidazoles, 1- (2- hydroxyl -3- butoxypropyl) -2-ethyl-4-methylimidazole, 1- (2- hydroxyl -3- phenoxy propyl) -2- phenyl
Imidazoline, 1- (2- hydroxyl -3- fourth oxygen propyl group) -2- benzylimidazoline, 2- (dimethylaminomethyl) phenol, 2,4,6- tri- (two
Methylaminomethyl) phenol, N- beta-hydroxyethyl morpholine, 2- dimethylamino ethyl mercaptan, 2- mercaptopyridine, 2- sulfydryl benzo miaow
Azoles, 2-mercaptobenzothiazole, 4- mercaptopyridine, N, N- dimethylaminobenzoic acid, N, N- dimethylglycine, niacin, different cigarette
Acid, pyridine carboxylic acid, N, N- dimethylglycine hydrazides, N, N- neopentanoic acid hydrazides, hydroxyacyl hydroxyacyl hydrazine and isonicotinic acid hydrazide.
In addition, being used as the example for preparing the epoxide of raw material of amine adduct includes that polyphenol is (such as bisphenol-A, double
Phenol F, catechol and resorcinol) or the obtained bunching water of polyalcohol (such as glycerol and polyethylene glycol) and epichlorohydrin reaction
Glycerin ether；The glycidol ether that hydroxycarboxylic acid such as p- hydroxybenzoic acid and β oxynaphthoic acid and epichlorohydrin reaction obtain
Ester；The poly glycidyl ester that polybasic carboxylic acid such as phthalic acid and terephthalic acid (TPA) and epichlorohydrin reaction obtain；By 4,4'-
The glycidol amine compounds that diaminodiphenylmethane and m- amino-phenol obtain；Multi-functional epoxy compound's such as epoxidized phenol
Novolac resin, epoxidized cresol novolac resin and epoxidized polyolefin；And monofunctional epoxy compound such as butyl
Glycidol ether, phenyl glycidyl ether and glycidyl methacrylate.
As the isocyanate compound for preparing the raw material of amine adduct is used as, monofunctional isocyanates compound can be used
Such as n-butyl isocyanate, isopropyl isocyanate, phenyl isocyanate and benzyl mustard oil；Polyfunctional isocyanate compound such as six is sub-
It is methyl diisocyanate, toluene di-isocyanate(TDI), 1,5 naphthalene diisocyanate ester, diphenyl methane -4,4'- diisocyanate, different
Your ketone of fluorine diisocyanate, eylylene diisocyanate, to phenylene vulcabond, three isocyanide of 1,3,6- hexa-methylene
Acid esters and norbornane triisocyanate；And in its end contains the compound of isocyanate group (it is by above-mentioned multifunctional
Isocyanate compound reacts to obtain with active dydrogen compounds), also, the example of such compound includes toluene di-isocyanate(TDI)
That reacts with trimethylolpropane has the addition reaction product of isocyanate group in its end.
The example of carbamide compound as the raw material for preparing amine adduct includes urea, urea phosphate, urea oxalate, hydantoic acid, two
Acetylurea, dibenzoyl urea and trimethyl-urea.
The representative instance of commercially available amine adduct includes amine-epoxy adduct such as " ADEKA HARDENER H-3613S "
(trade name of Asahi Denka Co., Ltd), " ADEKA HARDENER H-3293S " be (Asahi Denka Co., Ltd
Trade name), " AMICURE PN-23 " (trade name of Ajinomoto Co., Ltd), " AMICURE MY-24 " (Ajinomoto
The trade name of Co., Ltd), " CUREDUCT P-0505 " (trade name of SHIKOKU chemical company)；Urea type adduct is such as
" FUJICURE FXE-1000 " (trade name of Fuji Kasei Kogyo Co., Ltd) and " FUJICURE FXR-1036 "
(trade name of Fuji Kasei Kogyo Co., Ltd).
In addition, by further with acid compound such as carboxylic acid compound and sulfoacid compound, isocyanate compound or ring
The surface of oxygen compound processing amine compounds (or amine adduct) to form the shell of modified product (adduct etc.) on the surface and
Obtain the hud typed curing agent.In addition, the masterbatch type curing agent is in the hud typed of the state mixed with epoxy resin
Curing agent.
The example of commercially available masterbatch type curing agent includes that " Novacure HX-3722 " (Asahi Kasei Epoxy is limited
The trade name of company), " Novacure HX-3742 " (trade name of Asahi Kasei Epoxy Co., Ltd), " Novacure
HX-3613 " (trade name of Asahi Kasei Epoxy Co., Ltd) etc..
In terms of the liquid-state epoxy resin of 100 parts by weight, in one embodiment, the content of the latent curing agent is
5 to 50 parts by weight.
In terms of the liquid-state epoxy resin of 100 parts by weight, in one embodiment, the content of the latent curing agent is
10 to 35 parts by weight.
The liquid phenolic resin of said components (c) is liquid under room temperature (i.e. 25 DEG C).The liquid phenolic resin can be with
It is made of a kind of phenolic resin, or can be the mixture of two or more phenolic resin.
The example of the liquid phenolic resin includes allylation novolac resin, diallyl bisphenol-A, acetylation
Phenol, diallyl Bisphenol F, and at 25 DEG C be liquid their mixture.The hydroxyl of the liquid phenolic resin
Equivalent is usually 80-200 grams per equivalent (g/eq).
Moreover it is preferred that novolac resin shown in above-mentioned formula (I) is the liquid epoxies.
In terms of the liquid-state epoxy resin of 100 parts by weight, in one embodiment, the content of the liquid phenolic resin is
0.1-25 parts by weight.
In addition it is also preferred that novolac resin shown in following formula is as the liquid phenolic resin:
In above-mentioned formula, R1 to R5 each independently represents H, the alkyl with 1 to 5 carbon atom or allyl and n table
Show 0 or bigger integer.R1 can each indicate different meanings into R5 on different phenyl ring.For example, leftmost
R3 on phenyl ring can be H, and the R3 on the phenyl ring of rightmost can be allyl.The liquid phenolic resin is preferably alkene
Propylated novolac resin, wherein at least one phenyl ring, R1 at least one expression allyl into R5.
Preferred liquid phenolic resin is that wherein R1 to R5 is H each independently, has 1 to 3 (preferably 1 or 2) a carbon
The alkyl or allyl and n of atom are novolac resins shown in the above-mentioned formula of 0 to 3 integer.
Most preferred liquid phenolic resin be wherein R1 to R5 be H or allyl each independently and n be 0 to 3 it is whole
Novolac resin shown in several above-mentioned formulas, and it has allyl at least on the phenyl ring of part.As such allyl
Change novolac resin, it is known to MEH8000 (hydroxyl equivalent 141g/eq), the MEH8005 of Meiwa Plastics Industry Company manufacture
(hydroxyl equivalent 135g/eq), MEH8010 (hydroxyl equivalent 130g/eq) and MEH8015 (hydroxyl equivalent 134g/eq).
The epoxy of said components (d)-silane copolymer compound is selected from the copolymerization chemical combination shown in lower formula (I) or formula (II)
Object:
Or
In formula (I) and formula (II), R is each independently CH3 or OCH3；M, n, o, p are respectively the different lists for repeating ratio
Position.
The component (d) is preferably the commodity E-102B of waste river chemical production.
The one-component epoxy resin composition in technical solution of the present invention embodiment is by mixing the component (a)
To (d), and if necessary, it is additionally added function ingredients and is obtained such as suitable stabilizer, diluent and filler.It is described
The mixing of component can carry out at room temperature, or can be heated to solidification temperature or lower temperature at a temperature of carry out.As
Kneader or blender can be used in mixing apparatus.
Next, the content of component (a) to (c) in the one-component epoxy resin composition will be described.
The content of component (b) is to be suitable for the cured amount of component (a).The solidification of component (a) refers to so that solidified resin
Mechanical strength be higher than the mode of degree required for intended application and solidify the component (a).In this case, solidified resin
Preferred mechanical strength be considered as being approximately equal to the main mechanical strength using in the case where latent curing agent.Component (b)
Content be usually rule of thumb rule and determine.Relative to the component (a) of 100 parts by weight, the content of component (b) be usually 50 to
120 parts by weight, preferably 80 to 120 parts.When the content of component (b) is not in above range, the machinery of solidified resin is strong
Degree is insufficient.
The content of component (c) is suitable for assigning the amount of the one-component epoxy resin composition high solidification property.It is described
High solidification property refers to that solidification temperature is low and curing time is short.Relative to the component (a) of 100 parts by weight, the content of component (c)
It can be 30 parts by weight or less, preferably 0.1 to 25 parts by weight.It is described when the content of component (c) is not in above range
The curing properties of one-component epoxy resin composition deteriorate.
In terms of one-component epoxy resin composition gross mass, the content of the component (d) is preferably between 0.1wt% (quality
Percentage composition) between 10wt%.The component (d) itself can sol gel so that in the component (d) with Si-O key
The CH3 scission of link of knot, and the Si-O for losing CH3 bond can be bonded each other with the Si-O of surrounding and form cross-linked structure, this crosslinking knot
The single component epoxy constituent in technical solution of the present invention embodiment and the adhesion between metal or glass can be improved in structure,
And because the bond number of Si-O increases, the endurance of epoxy resin can also improved.
The one-component epoxy resin composition of technical solution of the present invention embodiment can also include that nano particle is filled out
Fill agent.The nano particle filler includes the nano particles such as silica, titanium oxide or aluminium oxide.The nanometer particle can be embedded in
The cross-linked structure of above-mentioned one-component epoxy resin composition is bonded, and has one-component epoxy resin constituent of the invention
Better adhesive force and stability.In addition, nano particle hardness itself is harder, it can also make one-component epoxy resin group after solidification
It is improved at the hardness of object, but nano particle will cause viscosity rising, optionally can be suitable for addition.With one-component epoxy resin
Composition gross mass meter, the nano particle filling agent content are preferably between 1wt% between 10wt%.
The one-component epoxy resin composition of technical solution of the present invention embodiment can further contain silicon as needed
Alkane coupling agent, the silane coupling agent are not particularly limited, and the example includes gamma-amino propyl trimethoxy silicane, gamma-amino
Propyl-triethoxysilicane, γ mercaptopropyitrimethoxy silane, γ-methacryloxypropyl trimethoxy silane,
γ-glycidoxypropyltrime,hoxysilane, SH6062, SZ6030 are (limited by DowCorning ToraySilicone
Company's production) and KBE903, KBM803 (being produced by Shin-Etsu Shilicone Co., Ltd).
The one-component epoxy resin composition of technical solution of the present invention embodiment can contain diluent.With epoxy group
Compound, vinyl ethers, oxetane compound and polyalcohol be both suitable as the diluent.In addition, having epoxy
The compound of base, which can consider, to be contained in component (a).
The specific example of such diluent includes aliphatic alkyl-monoglycidyl ether or diglycidyl ether such as hexamethylene
Dimethanol diglycidyl ether, butyl glycidyl ether, 2- hexyl glycidyl ether and allyl glycidyl ether；Alkyl
Ethylene oxidic ester such as glycidyl methacrylate and tertiary carboxylic acid ethylene oxidic ester；Styrene oxide；Aromatic alkyl list shrinks
Glycerin ether such as phenyl glycidyl ether, cresyl glycidyl ether, p-s- butylphenyl glycidyl ether and nonyl phenyl glycidyl
Glycerin ether；Tetrahydrofurfuryl alcohol glycidol ether；Simple function or polyfunctional vinyl ethers such as cyclohexanedimethanol vinethene, three sweet
Alcohol divinyl ether and hydroxybutyl divinyl ether.
The one-component epoxy resin composition of technical solution of the present invention embodiment is under lower solidification temperature in short-term
Interior solidification.In one preferred embodiment, the solidification temperature of the one-component epoxy resin composition e.g., about 70
DEG C or it is higher, more preferably from about 75 DEG C or higher.Curing time depends on solidification temperature, such as when solidification temperature is about 75 DEG C,
The curing time in about 60 minutes, preferably in about 45 minutes.When solidification temperature is about 100 DEG C, the curing time
In about 20 minutes, preferably in about 10 minutes.
The viscosity of the one-component epoxy resin composition of the technical program is lower, and solidification temperature is relatively low, can add
It is superior in terms of work and storage characteristics, and there is long working life.Therefore, the one pack system ring of technical solution of the present invention embodiment
Epoxy resin composition can be used for being widely applied the such as sealant of semiconductor and glassy bond and EL device display such as applied to use
Sealant.
Hereinafter, will by embodiment, the present invention will be described in more detail, but the invention is not limited to these embodiments.
In addition, unless otherwise mentioned, unit such as part of expression amount and % are by weight in embodiment.
Embodiment 1
A kind of one-component epoxy resin composition, comprising: bisphenol A type epoxy resin, the bisphenol A type epoxy resin is in 25
DEG C be liquid, viscosity 13000 to 17000mPa.s, epoxide equivalent be 175 to 190g/eq；The bisphenol A type epoxy resin is
Nippon Kayaku company manufactures " RE-310S "；Latent curing agent, the latent curing agent are Asahi Kasei company
It manufactures " Novacure HX-3722 "；Allylation phenol system phenolic resin, the allylation phenol system phenolic resin are in 25 DEG C
Liquid, viscosity are 2000 ± 1000mPa.s, and epoxide equivalent is 141 ± 2g/eq, and the allylation phenol system phenolic resin is
Meiwa Plastics Industry Company manufactures " MEH 8000H "；The epoxy of formula (I)-silane copolymer compound；Silane coupling agent, the silicon
Alkane couplant is γ-glycidyl ether oxypropyltrimethoxysilane；Nano alumina particles.
Wherein, in terms of by the liquid-state epoxy resin for 100 parts by weight, the content of the latent curing agent is 35 weight
Part, the content of the liquid phenolic resin is 10 parts by weight, and the epoxy-silane copolymer compound content is 5 parts by weight, institute
Stating nano particle filling agent content is 5 parts by weight.
Detection obtains, and the viscosity of the one-component epoxy resin composition is lower, the time needed for viscosity increases to twice
Greater than two weeks, that is, have preferable storage stability.
Embodiment 2
It equably mixes and solidifies above-mentioned one-component epoxy resin composition, to obtain cured epoxy resin.Wherein,
Condition of cure is 75 degrees Celsius 45 minutes lower.
Detection obtains, and the epoxy resin cure is complete, and mechanical strength is preferable, namely explanation, the single-component epoxy
Resin combination has lower solidification temperature.
It is understood that for those of ordinary skill in the art, can do in accordance with the technical idea of the present invention
Various other changes and modifications out, and all these changes and deformation all should belong to the protection model of the claims in the present invention
It encloses.
Claims (12)
1. a kind of one-component epoxy resin composition, including liquid-state epoxy resin, for solidifying the latent of the liquid-state epoxy resin
Volt property curing agent, liquid phenolic resin and epoxy-silane copolymer compound.
2. one-component epoxy resin composition as described in claim 1, which is characterized in that the liquid-state epoxy resin includes choosing
From at least one of bisphenol A type epoxy resin, bisphenol f type epoxy resin, catechol and resorcinol.
3. one-component epoxy resin composition as described in claim 1, which is characterized in that the latent curing agent includes choosing
From at least one of amine compounds, imidazolium compounds and their adduct.
4. one-component epoxy resin composition as described in claim 1, which is characterized in that with the liquid epoxy of 100 parts by weight
Resin meter, the content of the latent curing agent are 5 to 50 parts by weight.
5. one-component epoxy resin composition as claimed in claim 4, which is characterized in that with the liquid epoxy of 100 parts by weight
Resin meter, the content of the latent curing agent are 10 to 35 parts by weight.
6. one-component epoxy resin composition as described in claim 1, which is characterized in that with the liquid epoxy of 100 parts by weight
Resin meter, the content of the liquid phenolic resin are 0.1 to 25 parts by weight.
7. one-component epoxy resin composition as described in claim 1, which is characterized in that the epoxy-silane copolymer chemical combination
Object is selected from the copolymerization shown in lower formula (I) or formula (II):
Or
In formula (I) and formula (II), R is each independently CH3 or OCH3；M, n, o, p are respectively the different units for repeating ratio.
8. one-component epoxy resin composition as described in claim 1, which is characterized in that with one-component epoxy resin composition
Gross mass meter, the epoxy-silane copolymer compound content is between 0.1wt% (mass percentage) between 10wt%.
9. one-component epoxy resin composition as described in claim 1, which is characterized in that the one-component epoxy resin combination
Object also includes nano particle filler.
10. one-component epoxy resin composition as claimed in claim 9, which is characterized in that the nano particle filler packet
Include silica, titanium oxide or aluminum oxide nanoparticle.
11. one-component epoxy resin composition as claimed in claim 9, which is characterized in that combined with one-component epoxy resin
Object gross mass meter, between 1wt% (mass percentage) to 10wt%, (quality percentage contains the nano particle filling agent content
Amount) between.
12. one-component epoxy resin composition as described in claim 1, which is characterized in that the one-component epoxy resin group
It closes object and also contains silane coupling agent.
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| CN201711065813.9A CN109749359A (en) | 2017-11-02 | 2017-11-02 | one-component epoxy resin composition |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103105734A (en) * | 2011-11-09 | 2013-05-15 | 达兴材料股份有限公司 | Photosensitive resin composition |
| CN103228696A (en) * | 2010-11-19 | 2013-07-31 | 汉高公司 | One component epoxy resin composition |
-
2017
- 2017-11-02 CN CN201711065813.9A patent/CN109749359A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103228696A (en) * | 2010-11-19 | 2013-07-31 | 汉高公司 | One component epoxy resin composition |
| CN103105734A (en) * | 2011-11-09 | 2013-05-15 | 达兴材料股份有限公司 | Photosensitive resin composition |
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