CN102443112A - Radiation-curable composition - Google Patents
Radiation-curable composition Download PDFInfo
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- CN102443112A CN102443112A CN2011103052860A CN201110305286A CN102443112A CN 102443112 A CN102443112 A CN 102443112A CN 2011103052860 A CN2011103052860 A CN 2011103052860A CN 201110305286 A CN201110305286 A CN 201110305286A CN 102443112 A CN102443112 A CN 102443112A
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- radiation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- 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
- C08K5/10—Esters; Ether-esters
- C08K5/101—Esters; Ether-esters of monocarboxylic acids
- C08K5/105—Esters; Ether-esters of monocarboxylic acids with phenols
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
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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)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
Abstract
The present invention provides a radiation-curable composition which has the following advantages: capability of quickly curing through irradiating a small amount of radiating ray for a short time, good adhesiveness for various substrates, and capability of forming a solidified coating film which has excellent corrosion resistance for the substrate at extreme conditions. The radiation-curable composition at least comprises the following components: (A) organic polysiloxane which is represented by a general formula (1), (B) phenyl derivative with propenyls and (C) radiation sensitizer, wherein, R1,R2,R3 in the general formula (1) are independent from one another and are univalent alkyl with 1-10 carbon atoms, X are groups which respectively comprise propenyl or methylpropenyl, and each X can be same or different. Besides, a and b are numbers between 0.1 and 0.9 and are independent from each other, c and d are numbers between 0 and 0.8 and are independent from each other (but c and d can not be 0 simultaneously), and simultaneously a,b,c,d satisfy a relationship of a+b+c+d=1.
Description
Technical field
The present invention relates to the good radiation-curing composition of corrosion such as electrode of electrical/electronic components or device; Particularly be suitable as electrical/electronic components sealing usefulness, low-light (level) solidified nature and few good radiation-curing composition of light quantity solidified nature, and the electricinstallation and/or the electronic installation that use said composition to form.
Background technology
Knownly come the solidified organopolysiloxane composition through the irradiation ultraviolet radiation isoradial.The organopolysiloxane that for example contains the ethene functional group with the organopolysiloxane composition that constitutes with the photopolymerization initiator, is that good radiation-curable optical fiber is with coating (patent documentation 1).But this compsn is low because of the tackyness to base material, and can't be as general sticking agent, or relevant coating or the cakingagent of electrical/electronic uses.
Its shortcoming is: though comprise the organopolysiloxane composition (patent documentation 2) that specific organopolysiloxane, photosensitizing agent, tetraalkyl silane or its partly hydrolysed condenses of (methyl) acryloxy with radioactive rays functionality form at molecular chain two ends and can improve through containing at least; But to the requirement of the requirement of the curing speed low-lightization of radiation exposure when solidifying, but fail fully to satisfy in recent years.
The prior art document
Patent documentation
Patent documentation 1: the special fair 4-25231 communique of Japan
Patent documentation 2: japanese kokai publication hei 11-302348 communique
Summary of the invention
The problem that the invention desire solves
For this reason; The 1st purpose of the present invention is to provide a kind of radiation-curing composition, and it only needs a spot of radioactive rays of short irradiation to get final product fast setting, various base materials are shown good tackyness, and can form under extreme conditions curing that the corrosion to base material has good effect by overlay film.
The 2nd purpose of the present invention is to provide good electricinstallation of product reliability and/or electronic installation.
Solve the means of problem
Above-mentioned each purpose of the present invention is to realize like this; A kind of radiation-curing composition; It is characterized in that; At least comprise: (A) with the organopolysiloxane of formula (1) expression, phenyl ester verivate that (B) has propenyl, and (C) radioactive rays sensitizer, and the electricinstallation and/or the electronic installation that use this radiation-curing composition.
General formula (1):
Wherein, the R in the general formula (1)
1, R
2, and R
3Be to be 1 valency alkyl of carbon number 1～10 independently of one another, X is the base that comprises propenyl or methylpropenyl, and each X can be identical or different respectively.In addition, a and b are to be more than 0.1 and less than 0.9 number independently of one another, and c and d are 0～0.8 (but c, d can not be 0 simultaneously) independently of one another, and it is the number that satisfies the relation of a+b+c+d=1 simultaneously.
1 valency alkyl of aforementioned carbonatoms 1～10 can be aromatic hydrocarbyl.In addition, aforementioned (A) composition, (B) composition and (C) the allotment ratio of composition, with respect to 100 mass parts (A) composition, being preferably (B) composition is 0.1～10000 mass parts, and (C) composition is 0.1～100 mass parts.Radiation-curing composition of the present invention, being preferably according to the vapor transmission rate after the curing of JIS Z 0208 mensuration is 20g/mm
2Radiation-curing composition below day.
The invention effect
Radiation-curing composition of the present invention is owing to can easily solidifying with the less energy irradiation, and is therefore then particularly useful with coating as the protection of the liquid crystal electrode that influenced by ultraviolet isoradial, organic EL electrode, plasma display electrode etc.
Embodiment
Below specify the present invention.Moreover, in this specification sheets (methyl) acryloxy ((meth) acryloyl), (methyl) propenyl, (methyl) propenoate etc. are used as the term that comprises acryloxy (acryloyl) and methacryloxy (methacryloyl), propenyl and methylpropenyl, propenoate and methacrylic ester respectively.And " Me " is that on behalf of ethyl, " Pr ", represent methylidene, " Et " represent propyl group, " iPr " to represent sec.-propyl.
[(A) organopolysiloxane]
The organopolysiloxane of (A) composition that uses among the present invention is the host of radiation-curing composition of the present invention with formula (1) expression.
General formula (1):
Wherein, the R in the general formula (1)
1, R
2, and R
3Be to be 1 valency alkyl of carbon number 1～10 independently of one another, X is the base that comprises propenyl or methylpropenyl, and each X can be identical or different respectively.In addition, a and b are to be more than 0.1 and less than 0.9 number independently of one another, and c and d are 0～0.8 (but c, d can not be 0 simultaneously) independently of one another, and it is the number that satisfies the relation of a+b+c+d=1 simultaneously.
The concrete example of 1 valency alkyl of above-mentioned carbonatoms 1～10 for example can be enumerated: alkyl such as methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, hexyl, heptyl, 2-second hexyl, octyl group, nonyl; Naphthenic base such as cyclohexyl, suberyl; Thiazolinyls such as vinyl, allyl group, propenyl, pseudoallyl, crotonyl, hexenyl; Aryl such as phenyl, tolyl; Aralkyl such as benzyl, styroyl, 3-hydrocinnamyl; And at least a portion that will be binding on the Wasserstoffatoms on these basic carbon atoms is substituted by substituent chloromethyl, cyanoethyls, 3,3 such as halogen atom, cyanic acid, 3-trifluoro propyl etc.
In the organopolysiloxane of (A) composition that uses among the present invention, be preferably whole R especially
130 moles of % above be phenyl, be phenyl more than 50 moles of % more preferably.
In the general formula (1), X is the 1 valency organic radical that comprises propenyl or methylpropenyl.Its concrete example is shown in the following formula, but the present invention is not limited to this.
CH
2＝CHCOOCH
2 -、CH
2＝C(CH3)COOCH
2 -、CH
2＝CHCOOC
2H
4 -、CH2＝CHCOOC
3H
6 -、CH
2＝C(CH
3)COOC
3H
6 -、
In the present invention, be preferably the person of containing the propenyl among these, be preferably CH especially
2=CHCOOCH
2 -, CH
2=CHCOOC
3H
6 -
With the preferred concrete example of the organopolysiloxane of aforementioned formula (1) expression, for example can enumerate: with the represented person of following general formula (2).
General formula (2):
(PhSiO
3/2)
a((Me)
2SiO
2/2)
b(XSiO
3/2)
c
Wherein, a, b and c a, b and the c with general formula (1) separately are identical, and X is CH
2=CHCOOC
3H
6 -
(A) weight average molecular weight of the organopolysiloxane of composition is preferably 300～30000, more preferably 400～10000, is preferably 500～5000 especially.
The organopolysiloxane of this (A) composition is because of having (methyl) propenyl as radioactive rays polymerizability base; So, and compsn of the present invention is solidified via irradiation ultraviolet radiation, far ultraviolet rays yue, electronics line, X ray, the polymerization easily of gamma-rays isoradial.Have, the organopolysiloxane of this (A) composition can use a kind separately again, use more than 2 kinds also capable of being combined.
The organopolysiloxane of aforementioned (A) composition be for example in the following formula represented as, can modulate through making the reaction that be hydrolyzed of corresponding alkoxyl silicone alkanes.
The phenyl ester verivate of propenyl [(B) have]
Among the present invention, the phenyl ester verivate with propenyl as (B) composition uses does not have special qualification, can enumerate for example with the following formula signifier.
X is OH, OMe, OEt
In the present invention, be preferably use vinylformic acid 2-hydroxyphenoxy propyl ester among them especially.
Among the present invention, (B) composition can use independent a kind of compound, use more than 2 kinds also capable of being combined.
In addition, (B) usage quantity of composition is preferably 0.1～10,000 mass parts with respect to 100 mass parts (A) composition, is preferably 1～1,000 mass parts especially.
[(C) radioactive rays sensitizer]
The radioactive rays sensitizer of (C) composition that uses among the present invention; Do not have special qualification; Be preferably benzoyl-compounds (or phenyl ketone compound) such as using diphenylketone, be preferably especially and use 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1-phenyl third-1-ketone, 1-(4-isopropyl phenyl)-2-hydroxy-2-methyl third-1-ketone etc. on the carbon atom of the alpha position of carbonyl, to have the benzoylation compound (or phenyl ketone compound) of hydroxyl.
Can oxidation 2,4 can be arranged for example in other preferred radioactive rays sensitizer of the present invention's use; 6-trimethylbenzoyl diphenylphosphine, bis oxide acyl group list organic radical phosphine, bis oxide (2,6-dimethoxy benzoyl-)-2,4; 4, oxidation organic phosphine compounds such as-tri-methyl-amyl phosphine; Benzoin ether compounds such as isobutyl-benzoin ether; Ketal compounds such as phenyl methyl ketone diethyl ketal; Thioxanthone (thioxanthone) based compound; Methyl phenyl ketone based compound etc.
Among the present invention, (C) the radioactive rays sensitizer of composition can only use independent a kind, use more than 2 kinds also capable of being combined.
The usage quantity of (C) composition among the present invention is so long as get final product the effective solidified amount of compsn of the present invention; Do not have special restriction; With respect to 100 mass parts aforementioned (A) composition, be generally 0.1～100 mass parts, be preferably 0.5～50 mass parts, 1.0～25 mass parts more preferably.
[other allocates composition]
Except above-mentioned (A)～(C) the composition, in the limit that does not undermine the object of the invention and effect, can suitably allocate other composition in the compsn of the present invention.Also adjustable shrinking percentage when for example solidifying with suitable adjustment, and the thermal expansivity of the cured article that obtains, physical strength, thermotolerance, resistance to chemical reagents, flame retardant resistance, thermal expansivity, air penetrability etc. are the various additives of purpose.
Among the present invention, inorganic fillers such as above-mentioned other allotment also adjustable for example aerosil of composition (fumed silica), aerosil, quartz powder, spun glass, red stone, titanium oxide, lime carbonate, magnesiumcarbonate; Radical polymerization inhibitors such as quinhydrones, methoxyl group quinhydrones, DBPC 2,6 ditertiary butyl p cresol (time limit of service prolongation agent) etc.
Radiation-curing composition of the present invention is above-mentioned through mixing (A)～(C) composition, and allocate composition according to other of needs and obtain.Through resultant composition is shone radioactive rays, compsn of the present invention solidifies apace, and after curing, manifests strong tackyness at once.
The radioactive rays that use among the present invention can be enumerated ultraviolet ray, far infrared rays, electronics line, X ray, gamma-rays etc., and easy by device, use viewpoint such as easy property, be preferably and use ultraviolet ray.Ultraviolet light source can be enumerated for example UVLED lamp, high voltage mercury lamp, ultrahigh pressure mercury lamp, metal halide lamp, carbon arc lamp, xenon lamp etc.(spike is long: 320～390nm) irradiation dose for the flap that for example compsn of the present invention is configured as the thickness of 2mm, is 100～2,400mJ/cm in ultraviolet ray
2, be preferably 200～800mJ/cm
2
Not only can be used as the for example protective membrane of the electrode of flat-panel monitor, plasma display etc. with the resulting cured article of compsn of the present invention; For also useful as the protective membrane or the sealing agent of various electrical/electronic portion article etc.; Even if under extreme condition, also has very good corrosion protection result.
Below, with synthetic example, embodiment etc. the present invention is detailed more, but the present invention is not as qualification with this.In addition, following " part " is that expression mass parts, " % " are expression quality %.
[synthetic example 1]
In the bottom of 2L has the separate type flask of embolism; Add phenyltrimethoxysila,e 295g (1.5 moles), dimethyldimethoxysil,ne 60.1g (0.5 mole), 3-acryloyl-oxy propyl trimethoxy silicane 23.4g (0.1 mole), toluene 270g, reach IPA (Virahol) 156g; After stirring under the room temperature, add 156g water and 17.2g 25% tetramethylammonium hydroxide aqueous solution.After stirring 3 hours under the room temperature, add 200g 10% biphosphate sodium water solution and neutralize.Separate the organic phase after washing, underpressure distillation obtains the product of representing with following formula.
Resulting organopolysiloxane is measured, is scaled cinnamic weight average molecular weight with GPC is 1612.
(PhSiO
3/2)
L((Me)
2SiO
2/2)
M(XSiO
3/2)
N
X is CH
2=CHCOOC
3H
6 -
In addition, L=0.71, M=0.24, N=0.05.
[synthetic example 2]
In the bottom of 5L has the separate type flask of embolism; Add phenyltrimethoxysila,e 237.9g (1.2 moles), dimethoxydiphenylsilane 244.36g (1.5 moles), 3-acryloyl-oxy propyl group methyl dimethoxysilane 174.6g (0.8 mole), 3-acryloyl-oxy propyl trimethoxy silicane 23.4g (0.1 mole), toluene 800g, reach IPA400g; After stirring under the room temperature, add the tetramethylammonium hydroxide aqueous solution of 400g water and 37.8g 25%.After stirring 3 hours under the room temperature, add 500g 10% biphosphate sodium water solution and neutralize.Separate the organic phase after washing, underpressure distillation obtains the product of representing with following formula.
Resulting organopolysiloxane is measured, is scaled cinnamic weight average molecular weight with GPC is 1145.
(PhSiO
3/2)
L((Ph)
2SiO
2/2)
M(MeXSiO
2/2)
N(XSiO
3/2)
O
Wherein, X is CH
2=CHCOOC
3H
6 -
In addition, L=0.33, M=0.42, N=0.22 and O=0.03.
[embodiment 1]
Mix following (A)～(C) composition, obtain radiation-curing composition of the present invention.
(A) synthetic routine 1 reaction products resulting: 50 mass parts
(B) vinylformic acid 2-hydroxyphenoxy propyl ester (the Japanese chemical drug system KAYARADR-128 of limited-liability company): 50 mass parts
(C) radioactive rays sensitizer (rich logical Chemiplas corporate system IRGACURE 907) 2.5 mass parts
Resultant composition is injected the mould of dark 1mm, wide 120mm, long 170mm, (illumination: 40W/cm in possessing the conveying belt stove of 2 metal halide mercury lamps
2) irradiation ultraviolet ray in 2 seconds (energy fluence: 200mJ), obtain cured article.
[embodiment 2]
Mix following (A)～(C) composition, obtain radiation-curing composition of the present invention.
(A) synthetic routine 2 reaction products resulting: 99 mass parts
(B) vinylformic acid 2-hydroxyphenoxy propyl ester (the Japanese chemical drug system KAYARADR-128 of limited-liability company): 1 mass parts
(C) radioactive rays sensitizer (Purakemu of Toyota Susho Corporation makes IRGACURE 907) 2.5 mass parts
Resultant composition is injected the mould of dark 1mm, wide 120mm, long 170mm, (illumination: 40W/cm in possessing the conveying belt stove of 2 metal halide mercury lamps
2) irradiation ultraviolet ray in 2 seconds (energy fluence: 200mJ), obtain cured article.
[embodiment 3]
Mix following (A)～(C) composition, obtain radiation-curing composition of the present invention.
(A) synthetic routine 1 reaction products resulting: 10 mass parts
(B) vinylformic acid 2-hydroxyphenoxy propyl ester (the Japanese chemical drug system KAYARADR-128 of limited-liability company): 90 mass parts
(C) radioactive rays sensitizer (Purakemu of Toyota Susho Corporation makes IRGACURE 907) 2.5 mass parts
Resultant composition is injected the mould of dark 1mm, wide 120mm, long 170mm, (illumination: 40W/cm in the conveying belt stove that possesses 2 metal halide mercury lamp lamps
2) irradiation ultraviolet ray in 2 seconds (energy fluence: 200mJ), obtain cured article.
<A variety of performance evaluation>
Rerum natura
To embodiment 1～3 resulting cured article, according to JIS K 6301, measure its hardness with spring loaded A type trier, measure the vapor transmission rate according to JIS Z 0208.Its result is shown in table 1.
[comparative example 1]
Except the organopolysiloxane of (A) composition that will be used in embodiment 1 changes to the polyurethane propenoate (Japanese chemical drug corporate system UX-4101), carry out equally with embodiment 1, the modulation group compound carries out the test identical with embodiment 1.Its result is shown in table 1.
Table 1
Can know by the result of table 1 and to know that radiation-curing composition of the present invention not only shines less energy and can fully solidify, also confirm that the water vapor permeability of resulting cured article is very little.
The worker produces practicality
Radiation-curing composition of the present invention is because of can easily solidifying with the less energy irradiation; Coating is used in the protection that not only can be used as the liquid crystal electrode that influenced by ultraviolet isoradial, organic EL electrode, plasma display electrode; Coating is used in the protection that also can be used as various electrical/electronic portion article, and is extremely useful on industry.
Claims (6)
1. a radiation-curing composition is characterized in that, comprises at least: (A) with the organopolysiloxane of formula (1) expression, phenyl ester verivate that (B) has propenyl, and (C) radioactive rays sensitizer;
Wherein, the R in the general formula (1)
1, R
2, and R
3Be to be 1 valency alkyl of carbon number 1～10 independently of one another, X is the base that comprises propenyl or methylpropenyl, and each X is identical or different respectively; In addition, a and b are to be more than 0.1 and less than 0.9 number independently of one another, and c and d are 0～0.8 (but c, d can not be 0 simultaneously) independently of one another, and are the number of the relation that satisfies a+b+c+d=1.
2. radiation-curing composition according to claim 1 is characterized in that, aforementioned R
1, R
2, and R
3In at least one is the aromatic hydrocarbyl of carbon number 6～10.
3. radiation-curing composition according to claim 1 and 2; It is characterized in that; Aforementioned (A) composition, (B) composition reach (C) the allotment ratio of composition, and with respect to 100 mass parts (A) composition, (B) composition is that 0.1～10000 mass parts, (C) composition are 0.1～100 mass parts.
4. radiation-curing composition according to claim 1 and 2 is characterized in that, is 20g/mm according to the vapor transmission rate after the curing of JIS Z 0208 mensuration
2Below day.
5. radiation-curing composition according to claim 3 is characterized in that, is 20g/mm according to the vapor transmission rate after the curing of JIS Z0208 mensuration
2Below day.
6. electricinstallation and/or electronic installation; It is electricinstallation and/or electronic installation through the resin cured matter sealing; It is characterized in that the aforementioned resin cured article is by solidifying the resin cured matter that forms according to any described radiation-curing composition of claim 1 to 5.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010224725 | 2010-10-04 | ||
| JP2010-224725 | 2010-10-04 | ||
| JP2011177621A JP2012097251A (en) | 2010-10-04 | 2011-08-15 | Radiation-curable composition |
| JP2011-177621 | 2011-08-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102443112A true CN102443112A (en) | 2012-05-09 |
Family
ID=46006080
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011103052860A Pending CN102443112A (en) | 2010-10-04 | 2011-09-30 | Radiation-curable composition |
Country Status (2)
| Country | Link |
|---|---|
| KR (1) | KR20120035118A (en) |
| CN (1) | CN102443112A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63117024A (en) * | 1986-11-05 | 1988-05-21 | Toshiba Silicone Co Ltd | Ultraviolet-curable silicone composition |
-
2011
- 2011-09-30 CN CN2011103052860A patent/CN102443112A/en active Pending
- 2011-09-30 KR KR1020110099639A patent/KR20120035118A/en not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63117024A (en) * | 1986-11-05 | 1988-05-21 | Toshiba Silicone Co Ltd | Ultraviolet-curable silicone composition |
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| Publication number | Publication date |
|---|---|
| KR20120035118A (en) | 2012-04-13 |
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Application publication date: 20120509 |