CN101671483A - Curable silicone resin composition, cured product thereof, and opaque silicone adhesive sheet formed from the composition - Google Patents
Curable silicone resin composition, cured product thereof, and opaque silicone adhesive sheet formed from the composition Download PDFInfo
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- CN101671483A CN101671483A CN200910174354A CN200910174354A CN101671483A CN 101671483 A CN101671483 A CN 101671483A CN 200910174354 A CN200910174354 A CN 200910174354A CN 200910174354 A CN200910174354 A CN 200910174354A CN 101671483 A CN101671483 A CN 101671483A
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
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- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
- C08G77/70—Siloxanes defined by use of the MDTQ nomenclature
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- 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
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Abstract
Disclosed are a curable silicone resin composition, a cured product thereof, and the opaque silicone adhesive sheet formed from the conposition. The curable silicone resin composition is solid at roomtemperature, the composition including: (A) an organopolysiloxane having a resin structure consisting of specific siloxane units, (B) an organohydrogenpolysiloxane having a resin structure consistingof specific siloxane units, (C) a platinum group metal-based catalyst, (D) either one or both of an opaque pigment and an opaque dye, and (E) a reaction retarder, in which a layer of thickness 100 [mu]m formed from a cured product of the composition exhibits a light transmittance of not more than 5% across the entire visible light range. The composition is solid at room temperature and thereforeeasy to handle. Further, the composition is useful for producing an opaque silicone adhesive sheet. A cured product obtained by curing the composition can be used to protect a liquid crystal electrodeand shield the electrode from light, thereby preventing malfunction of the driver IC, and also exhibits excellent mechanical properties and flexibility, and displays minimal surface tack.
Description
Technical field
The opacifying property organosilicon adhesive sheet that the present invention relates to solidified nature organosilicon resin composition, its cured article and make by said composition.
Background technology
Usually, in liquid-crystal display (below, abbreviate LCD sometimes as), drive IC is installed being equipped with on the electrode that glass carries chip (chipon glass).The running that can make a mistake when accepting strong illumination of known this drive IC.Especially the mobile telephone that has photographic camera, because the effect of high lights such as camera flashlamp, drive IC is done the running that makes mistake easily.For the electrode of protecting LCD (below, be sometimes referred to as liquid crystal electrode) and shading, prevented the mistake running of drive IC in the past, and developed and used the electrode protecting agent that is added with opacifying property pigment.As such electrode protecting agent, use the resin of types such as solvent-borne type or dealcoholizing-type usually, but the time that spends during these resin solidifications is long, and its cured article has the strong shortcoming of surface viscosity (タ Star Network).In order to overcome this shortcoming, also developed the electrode protecting agent that uses the fast and uv curing resin that reliability is high of curing speed, but owing to add opacifying property pigment, thereby the inside solidification reduction, poor practicability.So, developed with uv curing resin again and coated liquid crystal electrode, and make solidify when ultra-violet solidified after, with the method for photo-shield strip protection, but because operation is long and complicated, so productivity reduces easily, and the problem that exists cost to increase.
In addition, as prior art related to the present invention, for example, can enumerate the technology of putting down in writing in the following patent documentation.
The prior art document
Patent documentation
[patent documentation 1] TOHKEMY 2001-013513 communique
Summary of the invention
The problem that invention will solve
The object of the present invention is to provide a kind of solidified nature organosilicon resin composition, solidify cured article that obtains and the opacifying property organosilicon adhesive sheet of making by said composition by making said composition; described solidified nature organosilicon resin composition is owing to be solid at room temperature; therefore be easy to handle; described cured article plays the effect of protection and shading to liquid crystal electrode; can prevent the mistake running of drive IC; and mechanical characteristics, flexible are good, and surface viscosity is little.
The method of dealing with problems
In order to address the above problem, processes such as the present inventor are concentrated on studies, found that by adopting following solidified nature organosilicon resin composition, its cured article and can addressing the above problem, so finished the present invention by the opacifying property organosilicon adhesive sheet that said composition is made.
That is to say, the first, the invention provides a kind of solidified nature organosilicon resin composition, it is a solid state at room temperature, it contains:
(A) organopolysiloxane of resin structure, it comprises following structure: this structure is by R
1SiO
1.5Unit, R
2 2SiO unit and R
3 aR
4 bSiO
(4-a-b)/2The unit constitutes, and described R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50, wherein, and R
1, R
2And R
3Represent hydroxyl, methyl, ethyl, propyl group, cyclohexyl or phenyl independently of one another, R
4Represent vinyl or allyl group independently, a is 0,1 or 2, and b is 1 or 2, and a+b is 2 or 3;
(B) the organic hydride polysiloxane of resin structure, it comprises following structure: this structure is by R
1SiO
1.5Unit, R
2 2SiO unit and R
3 cH
dSiO
(4-c-d)/2The unit constitutes, and described R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50, wherein, and R
1, R
2And R
3Represent hydroxyl, methyl, ethyl, propyl group, cyclohexyl or phenyl independently of one another, c is 0,1 or 2, d is 1 or 2, and c+d is 2 or 3, and the amount that (B) is bonded in the hydrogen atom on the Siliciumatom in the composition is 0.1～4.0 with respect to the mol ratio of vinyl in (A) composition and allylic total amount;
(C) platinum metals class catalyzer: significant quantity;
(D) opacifying property pigment, opacifying property dyestuff or opacifying property pigment and opacifying property dyestuff; And
(E) reaction suppressor, and,
The layer of the thickness 100 μ m that made by the cured article of described solidified nature organosilicon resin composition has the transmittance below 5% in whole visible region.
The second, the invention provides a kind of silicone resin cured article, it is solidified to form above-mentioned solidified nature organosilicon resin composition.
The 3rd, the invention provides a kind of opacifying property organosilicon adhesive sheet, it is to be made by above-mentioned solidified nature organosilicon resin composition.
The effect of invention
Because solidified nature organosilicon resin composition of the present invention at room temperature is a solid, it has following advantage: the first, be easy to handle, easily be processed into different shape (for example, sheet); Second; even through after the prolonged preservation; the Opacifying pigment of filling in the said composition etc. also is difficult for separate and subside, for example protection and the shading of liquid crystal electrode and the mistake running that prevents drive IC of the electronic unit that can stably be used for electronic unit, especially needs shading.And, even said composition is with in the past also moulding easily of shaped device.Said composition just can easily be solidified under lower Heating temperature, so just can easily obtain mechanical characteristics, opacifying property is good, the cured article of the present invention that surface viscosity is little.Though this cured article is a hard, flexible is good.Said composition can easily be processed into the uniform tunicle of thickness.By with said composition or according to the method described above the opacifying property organosilicon adhesive sheet of gained press sticking or be fitted in electronic unit, the electronic unit that especially the needs shading surface of liquid crystal electrode for example; can be to electronic unit, especially need the electronic unit of shading to play the effect of protection and shading; more particularly; liquid crystal electrode is played the protection and the effect of shading, can prevent that the mistake of drive IC from operating.Like this, solidified nature organosilicon resin composition of the present invention is preferably as the protection coating of liquid crystal electrode, but is not limited to liquid crystal electrode, also can be at electronic unit, especially need to be extensive use of in the purposes such as protection coating of electronic unit of shading.
Embodiment
Below, the present invention will be described in more detail.Need to prove that in this manual, " room temperature " is meant 15～30 ℃ temperature.And Ph represents that phenyl, Me represent that methyl, Et represent that ethyl, Vi represent vinyl.
[solidified nature organosilicon resin composition]
Solidified nature organosilicon resin composition of the present invention contains following (A)～(E) composition.Composition of the present invention is easy to handle owing to be solid state at room temperature.Preferred composition of the present invention at room temperature is the plasticity-solid.
Below, describe with regard to each composition that contains in the solidified nature organosilicon resin composition of the present invention.
-(A) organopolysiloxane of resin structure-
(A) composition as one of important composition composition in the present composition is the organopolysiloxane of resin structure (being tridimensional network), and it contains following structure as part-structure: this structure is by R
1SiO
1.5Unit, R
2 2SiO unit and R
3 aR
4 bSiO
(4-a-b)/2The unit constitutes, and described R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50, preferred 8～40, more preferably 10～35 structure, wherein, and R
1, R
2And R
3Represent hydroxyl, methyl, ethyl, propyl group, cyclohexyl or phenyl independently of one another, R
4Represent vinyl or allyl group independently, a is 0,1 or 2, and b is 1 or 2, and a+b is 2 or 3.
Need to prove above-mentioned R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is that 5～50 structure is meant the two organo-siloxane chain structures of straight chain shown in the following general formula (1).
[Chemical formula 1]
(herein, m is 5～50 integer)
Preferred whole R that exist in the organo-siloxane of (A) composition
2 2At least a portion in the SiO unit, preferred 50 moles of % above (50～100 moles of %), preferred especially 80 moles of % above (80～100 moles of %) form the chain structure shown in the described general formula (1) in molecule.
In the molecule of (A) composition, R
2 2The unitary effect of SiO is to make polymer molecule extend into straight chain shape, R
1SiO
1.5The unit makes polymer molecule produce branch or makes its three-dimensional nettedization.R
3 aR
4 bSiO
(4-a-b)/2R in the unit
4Hydrosilation (hydrosilication takes place with the hydrogen atom (being the SiH yl) that is bonded on the following Siliciumatom in (being vinyl or allyl group independently), ヒ De ロ シ リ カization) addition reaction, performance makes composition solidified of the present invention effect thus, and described Siliciumatom is for containing the R of aftermentioned (B) composition
3 cH
dSiO
(4-c-d)/2Unitary Siliciumatom.
Consider the mol ratio of three kinds of essential siloxane units that comprise in preferred (A) composition, i.e. R from the characteristic of gained cured article
1SiO
1.5Unit: R
2 2SiO unit: R
3 aR
4 bSiO
(4-a-b)/2Unitary mol ratio is 90～24: 75～9: 50～1, preferred especially 70～28: 70～20: 10～2 (total amount is 100).
In addition, by gel permeation chromatography (GPC) record should (A) composition weight-average molecular weight (polystyrene conversion) in 3000～1000000, especially 10000～100000 scopes the time, this polymkeric substance is solid or semisolid, and operability, solidified nature etc. are good, and is therefore preferred.
The organopolysiloxane of such resin structure can be synthetic by following method: each unitary starting compound is made up, make that the amount of above-mentioned three kinds of siloxane units is desired mol ratio in the polymkeric substance that generates, for example, can be in the presence of acid, by carrying out cohydrolysis, next synthesizing of condensation (Jia Shui Fen Xie Shrink closes altogether).
Here, as R
1SiO
1.5Unitary raw material can be enumerated MeSiCl
3, EtSiCl
3, PhSiCl
3, chlorosilane classes such as propyltrichlorosilan, cyclohexyl trichlorosilane, with the corresponding respectively alkoxyl silicone alkanes such as methoxy silane class of these chlorosilane classes etc.
As R
2 2The unitary raw material of SiO can be enumerated ClMe
2SiO (Me
2SiO)
jSiMe
2Cl,
ClMe
2SiO(Me
2SiO)
k(PhMeSiO)
LSiMe
2Cl、
ClMe
2SiO(Me
2SiO)
k(Ph
2SiO)
LSiMe
2Cl、
(HO)Me
2SiO(Me
2SiO)
jSiMe
2(OH)、
(HO)Me
2SiO(Me
2SiO)
k(PhMeSiO)
LSiMe
2(OH)、
(HO)Me
2SiO(Me
2SiO)
k(Ph
2SiO)
LSiMe
2(OH)、
(MeO)Me
2SiO(Me
2SiO)
jSiMe
2(OMe)、
(MeO)Me
2SiO(Me
2SiO)
k(PhMeSiO)
LSiMe
2(OMe)、
(MeO) Me
2SiO (Me
2SiO)
k(Ph
2SiO)
LSiMe
2(OMe) etc., the integer (mean value) of the integer (mean value) of the integer (mean value) of the integer of j=3～48 (mean value), k=0～47, L=1～48 and k+L=3～48 herein.
In addition, R
3 aR
4 bSiO
(4-a-b)/2R is represented to be selected from the unit
3R
4SiO unit, R
3 2R
4 bSiO
0.5Unit, R
4 2SiO unit and R
3R
4 2SiO
0.5Unitary a kind of siloxane unit or the combination of siloxane unit more than 2 kinds.As its raw material, can enumerate Me
2ViSiCl, MeViSiCl
2, Ph
2ViSiCl, PhViSiCl
2Deng the chlorosilane class, the alkoxyl silicone alkanes such as methoxy silane class corresponding etc. with these chlorosilane classes difference.
In addition, in the present invention, when cohydrolysis by the above-mentioned raw materials compound and condensation manufacturing (A) composition organopolysiloxane, at R
1SiO
1.5Unit, R
2 2SiO unit, R
3 aR
4 bSiO
(4-a-b)/2Comprise siloxane unit in the combination more than 2 kinds in unit or these unit with silanol group.Usually, with respect to whole siloxane units, (A) the composition organopolysiloxane comprises the described siloxane unit that contains silanol group of about 10 moles of % following (0～10 mole of %), about preferred about 5 moles of % following (0～5 mole of %).As the described siloxane unit that contains silanol group, can enumerate, for example, (HO) SiO
1.5Unit, R
2' (HO) SiO unit, (HO)
2SiO unit, R
4(HO) SiO unit, R
4 2(HO) SiO
0.5Unit, R
3' R
4(HO) SiO
0.5Unit, R
4(HO)
2SiO
0.5Unit (R here,
2' and R
3' be outer above-mentioned of hydroxyl-removal about R
2And R
3Defined group, R
4As above-mentioned definition).Need to prove R
1, R
2And R
3In hydroxyl be meant hydroxyl in the above-mentioned siloxane unit that contains silanol group.
-(B) the organic hydride polysiloxane of resin structure-
(B) composition as one of important composition composition in the present composition is the organic hydride polysiloxane of resin structure (being tridimensional network), and it contains following linear siloxanes structure as part-structure: this structure is by R
1SiO
1.5Unit, R
2 2SiO unit and R
3 cH
dSiO
(4-c-d)/2The unit constitutes, and described R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50, preferred 8～40, more preferably 10～35, wherein, and R
1, R
2And R
3Represent hydroxyl, methyl, ethyl, propyl group, cyclohexyl or phenyl independently of one another, c is 0,1 or 2, and d is 1 or 2, and c+d is 2 or 3.
Need to prove, about said above-mentioned R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50 a structure, and the above-mentioned narration relevant with (A) composition is similar, is meant the R that exists in (B) composition
22The unitary at least a portion of SiO, preferred 50 moles of % above (50～100 moles of %), preferred especially 80 moles of % above (80～100 moles of %) form the straight chain organopolysiloxane chain structure shown in the above-mentioned general formula (1) in the molecule of (B) composition.
In the molecule of (B) composition, R
2 2The unitary effect of SiO is to make polymer molecule extend into straight chain shape, R
1SiO
1.5The unit makes polymer molecule produce branch or makes its three-dimensional nettedization.Be bonded in R
3 cH
dSiO
(4-c-d)/2Hydrogen atom on the Siliciumatom in the unit and above-mentioned (A) alkenyl generation hydrosilylation addition reaction that composition contained, thus performance makes composition solidified of the present invention effect.
Consider the mol ratio of three kinds of essential siloxane units that comprise in preferred (B) composition, i.e. R from the characteristic of gained cured article
1SiO
1.5Unit: R
2 2SiO unit: R
3 cH
dSiO
(4-c-d)/2Unitary mol ratio is 90～24: 75～9: 50～1, preferred especially 70～28: 70～20: 10～2 (total amount is 100).
In addition, consider that preferably the weight-average molecular weight (polystyrene conversion) of this (B) composition that records by gel permeation chromatography (GPC) is in 3000～1000000, especially 10000～100000 scopes from the aspects such as characteristic of operability, cured article.
The organic hydride polysiloxane of such resin structure can be synthetic by following method: each unitary starting compound is made up, make that the amount of above-mentioned three kinds of siloxane units is desired mol ratio in the polymkeric substance that generates, for example, can in the presence of acid, synthesize by carrying out cohydrolysis.
Here, as R
1SiO
1.5Unitary raw material can be enumerated MeSiCl
3, EtSiCl
3, Ph SiCl
3, chlorosilane classes such as propyltrichlorosilan, cyclohexyl trichlorosilane, with the corresponding respectively alkoxyl silicone alkanes such as methoxy silane class of these chlorosilane classes etc.
As R
2 2The unitary raw material of SiO can be enumerated,
ClMe
2SiO(Me
2SiO)
jSiMe
2Cl、
ClMe
2SiO(Me
2SiO)
k(PhMeSiO)
LSiMe
2Cl、
ClMe
2SiO(Me
2SiO)
k(Ph
2SiO)
LSiMe
2Cl、
(HO)Me
2SiO(Me
2SiO)
jSiMe
2(OH)、
(HO)Me
2SiO(Me
2SiO)
k(PhMeSiO)
LSiMe
2(OH)、
(HO)Me
2SiO(Me
2SiO)
k(Ph
2SiO)
LSiMe
2(OH)、
(MeO)Me
2SiO(Me
2SiO)
jSiMe
2(OMe)、
(MeO)Me
2SiO(Me
2SiO)
k(PhMeSiO)
LSiMe
2(OMe)、
(MeO) Me
2SiO (Me
2SiO)
k(Ph
2SiO)
LSiMe
2(OMe) etc., the integer (mean value) of the integer (mean value) of the integer (mean value) of the integer of j=3～48 (mean value), k=0～47, L=1～48 and k+L=3～48 herein.
In addition, R
3 cH
dSiO
(4-c-d)/2R is represented to be selected from the unit
3HSiO unit, R
3 2HSiO
0.5Unit, H
2SiO unit and R
3H
2SiO
0.51 kind of siloxane unit in the unit or the combination of siloxane unit more than 2 kinds.As its raw material, can enumerate Me
2HSiCl, MeHSiCl
2, Ph
2HSiCl, PhHSiCl
2Deng the chlorosilane class, the alkoxyl silicone alkanes such as methoxy silane class corresponding etc. with these chlorosilane classes difference.
In addition, in the present invention, when the cohydrolysis by the above-mentioned raw materials compound and the organic hydride polysiloxane of condensation manufacturing (B) composition, at R
1SiO
1.5Unit, R
2 2SiO unit, R
3 cH
dSiO
(4-c-d)/2Comprise the siloxane unit that contains silanol group in the combination more than 2 kinds in unit or these unit.Usually, with respect to whole siloxane units, (B) composition organic hydride polysiloxane comprises the described siloxane unit that contains silanol group of about 10 moles of % following (0～10 mole of %), preferred about 5 moles of % following (0～5 mole of %).As the described siloxane unit that contains silanol group, can enumerate, for example, (HO) SiO
1.5Unit, R
2' (HO) SiO unit, (HO)
2SiO unit, H (HO) SiO unit, H
2(HO) SiO
0.5Unit, R
3' H (HO) SiO
0.5Unit, H (HO)
2SiO
0.5Unit (R here,
2' and R
3' be the outer above-mentioned R of hydroxyl-removal
2And R
3Defined group).Need to prove R
1, R
2And R
3In hydroxyl be meant hydroxyl in the above-mentioned siloxane unit that contains silanol group.
(B) use level of composition organic hydride polysiloxane is: the amount that makes the hydrogen atom (SiH group) that is bonded in (B) composition on the Siliciumatom is 0.1～4.0 amount with respect to the mol ratio of vinyl in (A) composition and allylic total amount, especially preferably making above-mentioned mol ratio is 0.5～3.0 amount, and more preferably making above-mentioned mol ratio is 0.8～2.0 amount.Above-mentioned mol ratio is lower than 0.1 o'clock curing reaction can't carry out, and is difficult to obtain the organosilicon cured article, and above-mentioned mol ratio is higher than at 4.0 o'clock because unreacted SiH remains in the cured article in a large number, the rerum natura that becomes cured article through the time reason that changes.
In the present invention, in order to give cementability, preferred (A) and (B) one of composition or both are contained silanol group.At the organopolysiloxane of (A) composition or (B) in the organic hydride polysiloxane of composition, the amount of this silanol group is 0.01～0.3 mole/100g, preferred 0.05～0.2 mole/100g.When if the content of silanol group is too much, the changes in hardness fierceness after the curing, therefore not preferred.In addition, if the content of silanol group is very few, then cementability can not be not fully exerted.
-(C) platinum metals class catalyzer-
This catalyst component is the catalyzer that adds for the addition curing reaction that causes the present composition, comprises catalyzer such as platinum class, palladium class, rhodium class.As this catalyzer, can use in the past as promoting the known any catalyzer of hydrosilation reaction.Consider cost etc., can enumerate, platinum class catalyzer such as platinum, platinum black, Platinic chloride, for example H
2PtCl
6PH
2O, K
2PtCl
6, KHPtCl
6PH
2O, K
2PtCl
4, K
2PtCl
4PH
2O, PtO
2PH
2O, PtCl
4PH
2O, PtCl
2, H
2PtCl
4PH
2O (herein, p is a positive integer) etc., or hydro carbons such as these catalyzer and alkene, alcohol or contain the complex compound etc. of the organopolysiloxane of vinyl.These catalyzer can use a kind separately, also can will be used in combination more than 2 kinds.
(C) use level of composition gets final product for being used for the solidified significant quantity, usually, the platinum metals meter, by mass conversion, with respect to above-mentioned (A) composition and (B) total amount of composition be the scope of 0.1～500ppm, preferred especially 0.5～100ppm.
-(D) any in opacifying property pigment and the opacifying property dyestuff or both-
(D) composition is any or both in opacifying property pigment and the opacifying property dyestuff, in order to give opacifying property to composition of the present invention, cured article and opacifying property organosilicon adhesive sheet, adds above-mentioned (D) composition in composition of the present invention.As (D) composition, be below 5% as long as can make the transmittance of layer in whole visible regions of the thick 100 μ m that make by the gained cured article, can be the opacifying property pigment and the opacifying property dyestuff of any known, preferred especially black pigment and/or dyestuff.As opacifying property pigment, for example can enumerate carbon class pigment such as carbon black or black oxidation iron oxide red pigment inorganic black pigments of opacifying property such as (?ベ Application ガ ラ) etc.As the opacifying property dyestuff, for example can enumerate opacifying property organic dye such as the organic black dyes of opacifying property etc.(D) particle diameter of composition is not particularly limited, particle diameter (for example, the accumulating weight average diameter D that records as the particle size distribution that is undertaken by the laser diffractometry that uses CILAS LASER determinator etc.
50Or meso-position radius) scope, preferred 10nm is above, more preferably 10～1000nm, preferred especially 10～500nm.The preferred inorganic black pigment of the above opacifying property of particle diameter 10nm that uses is as (D) composition.(D) composition can use a kind also can will be used in combination more than 2 kinds separately.
With respect to (A)～(C) composition of 100 mass parts altogether, the use level of preferred (D) composition in the scope of 0.01～10 mass parts, the more preferably scope of 0.5～5 mass parts.
-(E) reaction suppressor-
(E) composition is a reaction suppressor, in order to prevent that before using (E) composition composition of the present invention carries out addition reaction and causes said composition to be solidified, interpolation (E) composition in composition of the present invention.As (E) composition, as long as can suppress the promoted addition reaction of platinum metals class catalyzer, can be the reaction suppressor of any known, for example can enumerate, be selected from compound in contents of ethylene such as tetramethyl-tetrem thiazolinyl cyclotetrasiloxane high organopolysiloxane, vinyl silanes, triallyl isocyanurate, toxilic acid alkyl ester, alkynol class and silane-modified thing thereof and silicone-modified thing, hydrogen peroxide, Tetramethyl Ethylene Diamine, benzotriazole and composition thereof etc.(E) composition can use a kind also can will be used in combination more than 2 kinds separately.With respect to per 100 mass parts (A) composition, the use level of preferred (E) composition in the scope of 0.001～1.0 mass parts, the more preferably scope of 0.005～0.5 mass parts.
-other composition-
Except above-mentioned (A)～(E) composition, optionally also can the known various additives of interpolation itself in the composition of the present invention.
Inorganic filler:
Can add inorganic filler in the composition of the present invention.As inorganic filler, can be the inorganic filler of any known, for example can enumerate non-enhancing inorganic fillers such as enhancing property such as thermal silica, fumed titanium dioxide inorganic filler, lime carbonate, Calucium Silicate powder, titanium dioxide, zinc oxide etc.Inorganic filler can use a kind also can will be used in combination more than 2 kinds separately.With respect to (A) of 100 mass parts altogether and (B) composition, the use level of inorganic filler can be below 600 mass parts in the scope of (0～600 mass parts).
Bonding auxiliary agent
In order to give cementability, can optionally add bonding auxiliary agent (cementability imparting agent) in the composition of the present invention.Bonding auxiliary agent can use a kind also can will be used in combination more than 2 kinds separately.As bonding auxiliary agent, for example can enumerate, contain 2 kinds in molecule at least, preferably contain 2 kinds or 3 kinds and be selected from the hydrogen atom (SiH yl) that is bonded on the Siliciumatom, be bonded in alkenyl on the Siliciumatom (Si-CH=CH for example
2Base), the straight chain shape or the cyclic organic siloxane oligopolymer (several about 4～50, preferred about 4～20 of Siliciumatoms) of the functional group of alkoxysilyl (for example trimethoxysilyl), epoxy group(ing) (for example glycidoxy propyl group, 3,4-epoxy group(ing) cyclohexyl ethyl); Organic oxygen base silyl shown in the following general formula (2) (オ キ シ シ リ Le) modification tricarbimide ester cpds, its hydrolytic condensate (organic siloxane modified tricarbimide ester cpds); And the combination of these caking agents more than 2 kinds.
[Chemical formula 2]
(in the formula, R
5For organic group shown in the following formula (3) or contain the monovalence alkyl of aliphatics unsaturated link(age), and at least one R
5Be organic group shown in the formula (3).)
[chemical formula 3]
(R herein,
6Be the monovalence alkyl of hydrogen atom or carbonatoms 1～6, v is 1～6, especially 1～4 integer).
As the R in the general formula (2)
5The monovalence alkyl that contains the aliphatics unsaturated link(age), can enumerate cycloalkenyl group of carbonatoms 6～8 such as carbonatomss such as vinyl, allyl group, propenyl, pseudoallyl, butenyl, isobutenyl, pentenyl, hexenyl 2～8, particularly 2～6 alkenyl, cyclohexenyl etc.In addition, as the R in the formula (3)
6The monovalence alkyl, can enumerate, for example, alkyl such as methyl, ethyl, propyl group, sec.-propyl, butyl, isobutyl-, the tertiary butyl, amyl group, hexyl, cycloalkyl such as cyclohexyl, above-mentioned enumerate and R
5Relevant alkenyl and cycloalkenyl group, and carbonatomss such as aryl 1～8, especially 1～6 monovalence alkyl such as phenyl, preferred alkyl.
In addition, as bonding auxiliary agent, can enumerate 1,5-two (glycidoxy propyl group)-1,3,5,7-tetramethyl-ring tetrasiloxane, 1-glycidoxy propyl group-5-trimethoxysilylethylgroup group-1,3,5,7-tetramethyl-ring tetrasiloxane etc., and the compound shown in the following formula.
[chemical formula 4]
(in the formula, g and h are respectively the integer of 0～50 scope, and in the scope of g+h satisfied 2～50, preferred 4～20.)
[chemical formula 5]
[chemical formula 6]
In above-mentioned silicoorganic compound, the compound that can give good especially cementability to the gained cured article is to contain in a part to be bonded in the alkoxyl group on the Siliciumatom and to contain alkenyl or be bonded in the silicoorganic compound of the hydrogen atom (SiH yl) on the Siliciumatom.
With respect to 100 mass parts (A) composition, the use level of bonding auxiliary agent is generally about 10 mass parts following (i.e. 0～10 mass parts), preferably about 0.1～8 mass parts, 0.2～5 mass parts more preferably from about.If this use level is too much, then sometimes the hardness of cured article produced detrimentally affect, strengthens surface viscosity.
Preparation
Solidified nature organosilicon resin composition of the present invention can be by preparing desired composition uniform mixing.Usually cryopreservation solidifies to prevent it in refrigerator or refrigerator-freezer, makes its rapid curing by heating as required during use.
[cured article]
Cured article of the present invention can be by preferably being heated to composition of the present invention 50～150 ℃, more preferably being heated to 60～100 ℃, makes it to solidify and obtain.Be preferably 1～30 minute set time, more preferably 2～10 minutes.Also can 50～180 ℃, especially carry out 0.1～10 hour, 1～4 hour after fixing especially at 70～150 ℃.
The layer of the thick 100 μ m that made by cured article of the present invention has below 5% (promptly 0～5%), preferred 0～3% transmittance usually in whole visible regions.If this transmittance surpasses 5%, then the opacifying property of gained cured article easily becomes insufficient, promptly uses this cured article to coat liquid crystal electrode, can not play sufficient protection and shading and prevent the effect that the drive IC mistake operates this electrode sometimes.In the present invention, transmittance spectrophotometric determination.In addition, in the present invention, the visible region is meant the zone of 400～700nm.
[opacifying property organosilicon adhesive sheet]
Opacifying property organosilicon adhesive sheet of the present invention is the sheet of being made by above-mentioned solidified nature organosilicon resin composition, and its thickness is preferably 10～2000 μ m, 50～1000 μ m more preferably.This thickness can suitably be adjusted according to the transmittance of the cured article of said composition etc.
Opacifying property organosilicon adhesive sheet of the present invention can make by composition of the present invention is coated on the base material with film spreader or pressing machine etc.As base material, can enumerate PET film, the PET film that has been coated with releasing agent, fluoride resin class film etc.
Identical with solidified nature organosilicon resin composition of the present invention, opacifying property organosilicon adhesive sheet of the present invention cryopreservation in refrigerator or refrigerator-freezer solidifies to prevent it, makes its rapid curing by heating as required during use.Condition of cure is same as described above.
Embodiment
Below, provide synthesis example, embodiment and comparative example, the present invention is specifically described, but the present invention is not subjected to the restriction of following embodiment.Need to prove that the weight-average molecular weight in the following example is the polystyrene conversion value of measuring by gel permeation chromatography (GPC).
[synthesis example 1]
-contain the organopolysiloxane resins (A1) of vinyl-
With PhSiCl
3The organosilane of expression: 1142.1g (87.1 moles of %),
ClMe
2SiO (Me
2SiO)
33SiMe
2Cl:529g (3.2 moles of %),
MeViSiCl
2: after 84.6g (9.7 moles of %) is dissolved in the toluene solvant, be added drop-wise in the water, carry out cohydrolysis, wash again, neutralize, slough solvent after the dehydration, the synthetic resin (A1) that contains vinyl by neutralizing treatment.This resin is that weight-average molecular weight is 62000, fusing point is 60 ℃ solid.The contents of ethylene of this resin is 0.05 mole/100g.
[synthesis example 2]
-contain the organopolysiloxane resins (B1) of hydrogenation silyl (ヒ De ロ シ リ Le)-
With PhSiCl
3The organosilane of expression: 1142.1g (87.1 moles of %),
ClMe
2SiO (Me
2SiO)
33SiMe
2Cl:529g (3.2 moles of %),
MeHSiCl
2: after 69g (9.7 moles of %) is dissolved in the toluene solvant, be added drop-wise in the water, carry out cohydrolysis (adding water decomposition altogether), wash again, neutralize, slough solvent after the dehydration, the synthetic resin (B1) that contains the hydrogenation silyl by neutralizing treatment.This resin is that weight-average molecular weight is 58000, fusing point is 58 ℃ solid.The silyl content of this resin is 0.05 mole/100g.
[synthesis example 3]
-contain the organopolysiloxane resins (A2) of vinyl-
With PhSiCl
3The organosilane of expression: 5710.5g (81.8 moles of %),
ClMe
2SiO (Me
2SiO)
10SiMe
2Cl:2385g (9.1 moles of %),
Me
2After ViSiCl:361.5g (9.1 moles of %) is dissolved in the toluene solvant, be added drop-wise in the water, carry out cohydrolysis, wash again, neutralize, slough solvent after the dehydration, the synthetic resin (A2) that contains vinyl by neutralizing treatment.This resin is that weight-average molecular weight is 63000, fusing point is 63 ℃ solid.The contents of ethylene of this resin is 0.05 mole/100g.
[synthesis example 4]
-contain the organopolysiloxane resins (B2) of hydrogenation silyl-
With PhSiCl
3The organosilane of expression: 5710.5g (81.8 moles of %),
ClMe
2SiO (Me
2SiO)
10SiMe
2Cl:2385g (9.1 moles of %),
Me
2After HSiCl:283.5g (9.1 moles of %) is dissolved in the toluene solvant, be added drop-wise in the water, carry out cohydrolysis, wash again, neutralize, slough solvent after the dehydration, the synthetic resin (B2) that contains the hydrogenation silyl by neutralizing treatment.This resin is that weight-average molecular weight is 57000, fusing point is 56 ℃ solid.The hydrogenation silyl content of this resin is 0.05 mole/100g.
[embodiment 1]
The resin that contains vinyl (A1) with synthesis example 1 gained: 189g,
The resin that contains silyl (B1) of synthesis example 2 gained: 189g,
Ethynylcyclohexanol as the alkynol class of reaction suppressor: 0.6g,
1 quality % octanol solution: 0.2g of Platinic chloride,
Denka Black (trade(brand)name, the carbon black that Denka makes, particle diameter: about 35nm): 2g,
Bonding auxiliary agent shown in the following chemical formula: 4g mixes, and fully stirs the preparation organosilicon resin composition with the planetary stirring machine that is heated to 60 ℃.
[chemical formula 7]
Said composition is coated on the EPFT film with spreader, makes the black patch of thick 200 μ m or 100 μ m.This black patch 80 ℃ of heat dryings 5 minutes, is obtained the film of uncured (A level).
1. mechanical characteristics
(measure according to tensile strength (0.2mm is thick), hardness that JIS K 6301 measures the gained film with D type spring testing machine.6mm thick (be 0.2mm thick * 30)) and extensibility (0.2mm is thick).
2. Biao Mian viscosity
Confirm the surface viscosity of gained film by finger touch.In addition, this film is placed commercially available silver powder (median size 5 μ m), take out the back blow air, whether the dust-like silver powder that test sticks to the surface can be blown off.
More than each measurement result as shown in table 1.
3.[apply the conductive test under the voltage]
Reliability when using adhesive sheet of the present invention to protect the LCD electrode in order to estimate is carried out following test.In comb-type electrode (live width: 25 μ m, distance between centers of tracks: the size of 25 μ m, integral body: 10mm * 10mm, material: above-mentioned black patch is set on surface aluminium),, solidified 10 minutes, obtain estimating and use sample at 80 ℃ from the top crimping.Apply at 85 ℃/85%RH/ under the condition of 5V constant voltage the gained evaluation is carried out conductive test with sample, measure the sample that the corrosion because of electrode causes opening circuit and account for all samples (50 s') ratio.The result is as shown in table 2.
4. transmittance
With the transmittance of spectrophotometric determination gained film (0.1mm is thick) in whole visible regions.The result is as shown in table 3.
[embodiment 2]
Replace the resin that contains vinyl (A1) of synthesis example 1 gained of use among the embodiment 1 and the resin that contains the hydrogenation silyl (B1) of synthesis example 2 gained with the resin that contains vinyl (A2) of synthesis example 3 gained and the resin that contains the hydrogenation silyl (B2) of synthesis example 4 gained respectively, in addition, prepare organosilicon resin composition according to method similar to Example 1, estimate.The result is shown in table 1～3.
[comparative example 1]
With the organosilicon resin composition that uses among commercially available ultra-violet solidified silicone resin KJC-7805 (trade(brand)name, SHIN-ETSU HANTOTAI's chemical industry (strain) is made) the replacement embodiment 1, and to use wavelength 365nm, intensity 80W/cm
2Ultraviolet ray replace for 2 seconds 80 ℃ of heating 10 minutes 40 ℃ of irradiations, in addition the preparation cured article, according to method operation similar to Example 1, is estimated.The result is shown in table 1～3.
[comparative example 2]
With the room temp solidified silicone resin X-35-116BS of commercially available condensed type (trade(brand)name, SHIN-ETSU HANTOTAI's chemical industry (strain) system) organosilicon resin composition that uses among the replacement embodiment 1, and replaced in 24 hours 80 ℃ of heating 10 minutes with at room temperature in air, placing, the preparation cured article, in addition, according to method operation similar to Example 1, estimate.The result is shown in table 1～3.
[table 1]
| Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 | |
| ??SiH/SiVi(*1) | ??1.0 | ??1.0 | ??1.0 | ??1.0 |
| Condition of cure | 80 ℃/10 minutes | 80 ℃/10 minutes | As described in specification sheets | As described in specification sheets |
| Hardness (TypeD) | ??40 | ??40 | 20 (A types) | 50 (A types) |
| Elongation (%) | ??15 | ??15 | ??100 | ??50 |
| Tensile strength (MPa) | ??7 | ??6 | ??1 | ??1 |
| Silver powder adheres to due to the surface adhesion | Do not have | Do not have | Have | Have |
(notes)
* 1: be bonded in hydrogen atom on the Siliciumatom in the resin that contains the hydrogenation silyl with respect to the mol ratio of the vinyl on the Siliciumatom that is bonded in the resin that contains vinyl
[table 2]
| Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 | |
| 100 hours | ??0/50 | ??0/50 | ??0/50 | ??0/50 |
| 200 hours | ??0/50 | ??0/50 | ??0/50 | ??0/50 |
| 300 hours | ??0/50 | ??0/50 | ??5/50 | ??0/50 |
| 400 hours | ??0/50 | ??0/50 | ??15/50 | ??0/50 |
| 500 hours | ??0/50 | ??0/50 | ??25/50 | ??10/50 |
[table 3]
| Measure wavelength | Embodiment 1 | Embodiment 2 | Comparative example 1 | Comparative example 2 |
| ??400nm | ??0％ | ??0％ | ??0％ | ??80％ |
| ??700nm | ??0％ | ??0％ | ??0％ | ??90％ |
。
Claims (9)
1. solidified nature organosilicon resin composition, it is a solid at room temperature, wherein contains:
(A) organopolysiloxane of resin structure, it comprises following structure: this structure is by R
1SiO
1.5Unit, R
2 2SiO unit and R
3 aR
4 bSiO
(4-a-b)/2The unit constitutes, and described R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50, wherein, and R
1, R
2And R
3Represent hydroxyl, methyl, ethyl, propyl group, cyclohexyl or phenyl independently of one another, R
4Represent vinyl or allyl group independently, a is 0,1 or 2, and b is 1 or 2, and a+b is 2 or 3;
(B) the organic hydride polysiloxane of resin structure, it comprises following structure: this structure is by R
1SiO
1.5Unit, R
2 2SiO unit and R
3 cH
dSiO
(4-c-d)/2The unit constitutes, and described R
2 2The unitary at least a portion of SiO repeats continuously, and its repeat number is 5～50, wherein, and R
1, R
2And R
3Represent hydroxyl, methyl, ethyl, propyl group, cyclohexyl or phenyl independently of one another, c is 0,1 or 2, d is 1 or 2, and c+d is 2 or 3, and the amount that (B) is bonded in the hydrogen atom on the Siliciumatom in the composition is 0.1～4.0 with respect to the mol ratio of vinyl in (A) composition and allylic total amount;
(C) platinum metals class catalyzer: significant quantity;
(D) opacifying property pigment, opacifying property dyestuff or opacifying property pigment and opacifying property dyestuff; And
(E) reaction suppressor, and,
The layer of the thickness 100 μ m that made by the cured article of described solidified nature organosilicon resin composition has the transmittance below 5% in whole visible region.
2. solidified nature organosilicon resin composition according to claim 1, wherein, above-mentioned (A) and (B) one of composition or both are contained silanol group.
3. solidified nature organosilicon resin composition according to claim 1, wherein, above-mentioned (D) composition is black pigment, black dyes or both combinations.
4. solidified nature organosilicon resin composition according to claim 1, wherein, above-mentioned (D) composition is the above inorganic black pigment of opacifying property of particle diameter 10nm.
5. solidified nature organosilicon resin composition according to claim 1 wherein also contains bonding auxiliary agent.
6. according to each described solidified nature organosilicon resin composition in the claim 1～5, it is used for the electrode protection and the shading of liquid-crystal display.
7. silicone resin cured article, it makes, and each described solidified nature organosilicon resin composition is solidified to form in the claim 1～6.
8. cured article, it solidifies by the solidified nature organosilicon resin composition that makes that claim 1 is described and contain (A)～(E) component to form and makes, and this cured article has the transmittance below 5% in whole visible region under the state of the layer of making thickness 100 μ m.
9. opacifying property organosilicon adhesive sheet, it is made by each described solidified nature organosilicon resin composition in the claim 1～6.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2008233104 | 2008-09-11 | ||
| JP233104/08 | 2008-09-11 | ||
| JP2009188095A JP2010090363A (en) | 2008-09-11 | 2009-08-14 | Curable silicone resin composition, cured product thereof, and opaque silicone adhesive sheet formed from the composition |
| JP188095/09 | 2009-08-14 |
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| Publication Number | Publication Date |
|---|---|
| CN101671483A true CN101671483A (en) | 2010-03-17 |
| CN101671483B CN101671483B (en) | 2012-08-08 |
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| CN105960437B (en) * | 2014-02-19 | 2019-01-22 | 美国陶氏有机硅公司 | Reactive silicon composition, the hot melt material being made from it and curable hot melt composition |
| US9994745B2 (en) | 2014-03-26 | 2018-06-12 | Suzhou T-Power Optronics Technical Service Co. Ltd | Transparent organosilicon gel adhesive |
| WO2015143591A1 (en) * | 2014-03-26 | 2015-10-01 | 苏州桐力光电技术服务有限公司 | Transparent organic silicone gel binder |
| CN109651425A (en) * | 2017-10-12 | 2019-04-19 | 弗洛里光电材料（苏州）有限公司 | Isocyanate compound and its application containing multiple si-h bonds |
| CN109651425B (en) * | 2017-10-12 | 2021-02-26 | 弗洛里光电材料（苏州）有限公司 | Isocyanate compound containing multiple silicon-hydrogen bonds and application thereof |
| CN115667408A (en) * | 2020-05-26 | 2023-01-31 | 信越化学工业株式会社 | Two-liquid addition curing type silicone rubber composition |
| CN113736267A (en) * | 2021-09-27 | 2021-12-03 | 世晨材料技术(上海)有限公司 | Reversibly-stretched shading organic silicon film and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| KR101497157B1 (en) | 2015-02-27 |
| CN101671483B (en) | 2012-08-08 |
| KR20100031076A (en) | 2010-03-19 |
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