WO2012157225A1 - 室温硬化性ポリオルガノシロキサン組成物 - Google Patents
室温硬化性ポリオルガノシロキサン組成物 Download PDFInfo
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- WO2012157225A1 WO2012157225A1 PCT/JP2012/003071 JP2012003071W WO2012157225A1 WO 2012157225 A1 WO2012157225 A1 WO 2012157225A1 JP 2012003071 W JP2012003071 W JP 2012003071W WO 2012157225 A1 WO2012157225 A1 WO 2012157225A1
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- 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
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- 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
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
- C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
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- 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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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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- 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
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
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- 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
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
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- 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
- C08K5/54—Silicon-containing compounds
- C08K5/544—Silicon-containing compounds containing nitrogen
- C08K5/5445—Silicon-containing compounds containing nitrogen containing at least one Si-N bond
Definitions
- the present invention relates to a room temperature curable polyorganosiloxane composition, and in particular, consists of two components, a main agent composition and a crosslinking agent composition, which are cured at room temperature by mixing them in the air and are rubbery elastic bodies. Relates to a polyorganosiloxane composition.
- Condensation reaction type polyorganosiloxane that cures at room temperature to produce a rubbery elastic body is widely used as an elastic adhesive, coating material, electrical insulating sealing material, and as a building sealing material in the electrical and electronic industries. It is used.
- one-component type (one-packaging type) polyorganosiloxane which undergoes a curing reaction when it comes into contact with moisture in the air, weighs and mixes the base polymer and the crosslinking agent, catalyst, etc. immediately before use.
- the curing rate is slow and the deep part curability is poor.
- the two-component room temperature curable polyorganosiloxane has a high curing rate and excellent deep part curability.
- This composition is prepared by dividing into a main component composed of a polydiorganosiloxane having a molecular end blocked with a hydroxyl group and / or an alkoxy group and an inorganic filler, and a crosslinking component. And it is used as what is called a multi-packaging type room temperature curable composition preserve
- the crosslinking component is composed only of a crosslinking agent and a curing catalyst from the viewpoint of storage stability, so that the blending ratio of the crosslinking component to the main component is 1 to 3.
- the mass was extremely low, and variations in measurement and poor mixing were likely to occur.
- the mixing ratio of the main ingredient component and the crosslinking component may be set to about 100: 10 or an integer ratio in which the ratio of the crosslinking component is more than that from a practical viewpoint.
- the crosslinking component is composed only of the crosslinking agent and the curing catalyst.
- the same polymer as the base polymer (for example, silanol group-terminated polydiorganosiloxane) blended in the main component is used to increase the blending ratio of the crosslinking component. It can be considered that it is also added to a crosslinking component as an extender.
- a crosslinking component as an extender.
- the base polymer, the cross-linking agent and the catalyst coexist in the cross-linking component, not only the storage stability of the cross-linking component is deteriorated, but also the base polymer and the cross-linking agent Due to the poor compatibility, there was a problem of separation.
- the present invention has been made to solve these problems, and in a two-component room temperature curable polyorganosiloxane composition, it does not deteriorate properties such as deep curable property, uniformity of curing, and storage stability.
- An object of the present invention is to make it possible to appropriately adjust the blending ratio of the main component and the crosslinking component in accordance with the use of an automatic mixing / discharging machine or the like.
- the room temperature-curable polyorganosiloxane composition of the present invention comprises (A) (a1) a polyorganosiloxane having a hydroxyl group or an alkoxy group at the molecular end, (a2) a main agent composition containing an inorganic filler, and (B) ( b1) an organosilicon compound having three or more hydrolyzable groups bonded to a silicon atom in one molecule, or a partial hydrolyzate thereof, and (b2) a general formula: Wherein R 1 is an alkyl group or an alkoxyalkyl group which may be the same or different from each other, and R 2 and R 3 may be the same or different from each other.
- the component (a1) is preferably a polyorganosiloxane having a hydroxyl group at the molecular end.
- the organic compound containing a nitrogen atom can be contained as said (b3) curing catalyst.
- the general formula: (R 4 O) 3 Si—R 5 —NH—R 6 (wherein R 4 may be the same as or different from each other, an alkyl group or An alkoxyalkyl group, R 5 is an unsubstituted divalent hydrocarbon group, R 6 is a hydrogen atom, a monovalent hydrocarbon group unsubstituted or substituted with a halogen or a cyano group, or an aminoalkyl group And an amino group-containing alkoxysilane represented by formula (1).
- the main component composition (A) contains 1 to 500 parts by mass of the inorganic filler (a2) with respect to 100 parts by mass of the component (a1), and 100 parts by mass of the component (a1).
- the component (b2) is 0.5 to 20 parts by mass
- the (b3) curing catalyst is 0.01 to 10 parts by mass, and with respect to one hydroxyl group or alkoxy group of the component (a1)
- the (B) crosslinker composition can be blended so that the component (b1) has 2 to 20 alkoxy groups.
- the (A) main agent composition and the (B) crosslinking agent composition can be blended in a mass ratio of 100: 3 to 100: 20.
- the blending ratio of the main agent composition and the crosslinking agent composition can be appropriately adjusted according to the use of an automatic mixing / discharging machine or the like.
- the embodiment of the present invention is a two-component room temperature curable polyorganosiloxane composition obtained by blending (A) a main agent composition and (B) a crosslinking agent composition.
- the main agent composition contains (a1) a polyorganosiloxane having a hydroxyl group or an alkoxy group at the molecular end, and (a2) an inorganic filler.
- the cross-linking agent composition includes (b1) an organosilicon compound having three or more hydrolyzable groups as silicon functional groups in one molecule, or a partial hydrolyzate thereof, and (b2) a specific formula It contains a polyorganosiloxane having an alkoxy group at the molecular end represented, and (b3) a curing catalyst.
- each component which comprises (A) main ingredient composition and (B) crosslinking agent composition is demonstrated.
- (A1) component polyorganosiloxane having a hydroxyl group or an alkoxy group at the molecular end is usually used as a base polymer of a condensation type silicone rubber that can be cured at room temperature, and has a linear structure.
- the polydiorganosiloxane having is preferable. From the viewpoint of reaction rate, it is more preferable to use polyorganosiloxane having a hydroxyl group at the molecular end.
- examples of the organic group directly bonded to the silicon atom other than the hydroxyl group and the alkoxy group include an alkyl group such as a methyl group, an ethyl group, a propyl group, a butyl group, and a hexyl group; a vinyl group and an allyl group.
- Examples thereof include an alkyl group substituted with a halogen or cyano group. From the viewpoint of easy synthesis, a methyl group, a vinyl group or a phenyl group is preferred.
- the methyl group gives the lowest viscosity for the degree of polymerization of the siloxane, in addition to obtaining the raw material intermediate most easily.
- a polyorganosiloxane having a good balance between the extrusion workability of the composition before curing and the physical properties of the rubber-like elastic body after curing. Accordingly, those in which 85% or more of all organic groups are methyl groups are preferred, and those in which all organic groups other than hydroxyl groups and alkoxy groups are methyl groups are more preferred.
- a phenyl group is used. When oil resistance is particularly required, a 3,3,3-trifluoropropyl group is added to each organic group. It is desirable to have it as a part.
- the hydroxyl group or alkoxy group at the molecular terminal in the component (a1) contributes to curing by reaction with the hydrolyzable group or the like of the component (b1) described later.
- the alkoxy group include a methoxy group, an ethoxy group, and an isopropoxy group. From the viewpoint of reactivity, it preferably has a hydroxyl group or a methoxy group as a terminal group, and particularly preferably has a hydroxyl group.
- the viscosity of the component (a1) is preferably in the range of 0.1 to 1000 Pa ⁇ s at 23 ° C. If the viscosity is less than 0.1 Pa ⁇ s, the mechanical properties of the rubber-like elastic body after curing are not sufficient, and if it exceeds 1000 Pa ⁇ s, it is difficult to obtain a uniform composition when an inorganic filler described later is blended. Also, the moldability becomes worse.
- a more preferred viscosity is 0.3 to 100 Pa ⁇ s, and a particularly preferred viscosity is 0.3 to 50 Pa ⁇ s.
- A2 Inorganic filler (a2) The inorganic filler which is a component is mix
- Known inorganic fillers can be used, and examples include silica powder, fine mica powder, diatomaceous earth, calcium carbonate, zinc carbonate, iron oxide, titanium oxide, zinc oxide, pulverized quartz, and carbon black. .
- One kind may be used alone, or two or more kinds may be mixed and used.
- silica powder such as fumed silica (fumed silica), precipitated silica (wet silica), silica aerogel, ground quartz, and fused silica.
- the blending amount of the inorganic filler is 1 to 500 parts by mass, more preferably 3 to 200 parts by mass, and particularly preferably 3 to 150 parts by mass with respect to 100 parts by mass of the component (a1).
- A2 When the blending amount of the inorganic filler is less than 1 part by mass, the mechanical strength of the resulting cured product becomes insufficient, and when the blending amount exceeds 500 parts by mass, mixing becomes difficult and a uniform composition is obtained. I can't get it.
- (B1) An organosilicon compound having a hydrolyzable group or a partial hydrolyzate thereof
- (b1) An organosilicon compound having three or more hydrolyzable groups in one molecule as a component, or a partial hydrolyzate thereof,
- the component (a1) acts as a crosslinking agent, is hydrolyzed by moisture in the air, and easily undergoes a condensation reaction with the hydroxyl group (silanol group) or alkoxy group of the component (a1) to produce a cured product.
- Examples of the hydrolyzable group possessed by the component (b1) include alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group and a butoxy group; an alkoxyalkoxy group such as a methoxyethoxy group.
- Examples of the group bonded to the silicon atom other than the hydrolyzable group include a substituted or unsubstituted monovalent hydrocarbon group similar to the organic group directly bonded to the silicon atom in the component (a1). From the viewpoint of ease of synthesis and crosslinking rate, an alkyl group having 1 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms and a phenyl group are preferred.
- such component (b1) include tetraethoxylane, tetramethoxysilane, methyltrimethoxysilane, vinyltrimethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, ethyl orthosilicate, propyl orthosilicate, and the like.
- examples thereof include alkoxysilanes and partial hydrolysates thereof.
- Preferred is tetraethoxysilane or a partial hydrolyzate of tetramethoxysilane, and more preferred is a hydrolytic condensate having a polymerization degree of 3 to 15. When the degree of polymerization is less than 3, deep curability may be insufficient, and when the degree of polymerization exceeds 15, workability may be deteriorated.
- the amount of component (b1) is adjusted so that the number of hydrolyzable groups is 2 to 20 per hydroxyl group or alkoxy group in component (a1).
- the blending amount of the component (b1) is less than this range, the crosslinking is not sufficiently performed and a cured product having sufficient hardness is not obtained, and the storage stability of the crosslinking agent composition is deteriorated.
- it exceeds this range it is not only economically meaningless, but the balance between the curability of the composition and the mechanical properties after curing may be significantly reduced.
- the number of hydrolyzable groups in the component (b1) is more preferably 2 to 15 per hydroxyl group or alkoxy group in the component (a1).
- the component (b2) constituting the (B) crosslinking agent composition together with the component (b1) is the component (b1) in the (B) crosslinking agent composition.
- R 1 is an alkyl group or an alkoxyalkyl group which may be the same or different from each other.
- Alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group and hexyl group; alkoxyalkyl groups such as methoxyethyl group are exemplified, but methyl group and ethyl group are preferable, and methyl group is particularly preferable.
- R 2 and R 3 are each a monovalent hydrocarbon group which may be the same as or different from each other and is unsubstituted or substituted with a halogen or a cyano group.
- R 2 and R 3 are the same groups as the organic group directly bonded to the silicon atom in the component (a1), but an alkyl group is preferable, and a methyl group is particularly preferable.
- Y is an oxygen atom (oxo group) or a divalent hydrocarbon group.
- Examples of the divalent hydrocarbon group include alkylene groups such as a methylene group, an ethylene group, a propylene group, a tetramethylene group, a hexamethylene group, and a methylethylene group, and an oxygen atom (oxo group) or a propylene group is preferable.
- alkylene groups such as a methylene group, an ethylene group, a propylene group, a tetramethylene group, a hexamethylene group, and a methylethylene group
- an oxygen atom (oxo group) or a propylene group is preferable.
- a is 0 or 1
- b is 0 or 1. From the viewpoint of ease of synthesis, a and b are preferably equal.
- n represents an integer of 1 to 30.
- the value of n is more preferably in the range of 1 to 20, and further preferably in the range of 3 to 15.
- the blending amount of the component (b2) varies depending on ease of handling and composition of the composition, but is preferably 0.5 to 20 parts by mass with respect to 100 parts by mass of the component (a1). If the blending amount is less than 0.5 parts by mass, there is no effect by blending. Conversely, if the blending amount exceeds 20 parts by mass, the rubber strength of the cured product may decrease.
- the component (b3) is a curing catalyst for reacting the hydroxyl group or alkoxy group of the component (a1) with the hydrolyzable group of the component (b1) in the presence of moisture.
- curing catalysts include iron octoate, manganese octoate, zinc octoate, tin naphthate, tin caprylate, tin oleate, carboxylic acid metal salts; dibutyltin diacetate, dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin dioleate, diphenyltin Organotin compounds such as diacetate, dibutyltin oxide, dibutyltin dimethoxide, dibutylbis (triethoxysiloxy) tin, dioctyltin dilaurate; tetraethoxytitanium, tetrapropoxytitanium, te
- Examples of the organic compound having a nitrogen atom include diethylhydroxylamine, dimethylhydroxylamine, 1,1,3,3-tetramethylguanidine, 1,3-diphenylguanidine, 1,2,3-triphenylguanidine, 1, Guanidine derivatives such as 1,3,3-tetramethyl-2- [3- (trimethylsilyl) propyl] guanidine, and the general formula: (R 4 O) 3 Si—R 5 —NH—R 6
- An amino group-containing alkoxysilane represented by the formula (also referred to as amino group-substituted alkoxysilane) can be used.
- R 4 is an alkyl group or an alkoxyalkyl group which may be the same or different from each other.
- R 4 include the same alkyl groups as methyl group, ethyl group, propyl group, isopropyl group, butyl group, and hexyl group; alkoxyalkyl groups such as methoxyethyl group and the like, similarly to R 1 in the component (b2).
- R 5 is a divalent hydrocarbon group.
- R 6 is a hydrogen atom, a monovalent hydrocarbon group which is unsubstituted or substituted with a halogen or a cyano group, or an aminoalkyl group.
- Examples of the unsubstituted monovalent hydrocarbon group include alkyl groups such as methyl group, ethyl group, propyl group, and butyl group; arylene groups such as phenylene group and tolylene group; alkylene arylenes such as methylenephenylene group and ethylenephenylene group Groups and the like.
- Examples of aminoalkyl groups include aminoethyl groups and N-aminoethylaminoethyl groups.
- amino group-containing alkoxysilane represented by the above general formula
- aminomethyltriethoxysilane ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, and N- ( ⁇ -aminoethyl) amino.
- examples include methyltributoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltriethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane, ⁇ -anilinopropyltriethoxysilane Is done.
- Preferred organic compounds having a nitrogen atom are ⁇ -aminopropyltriethoxysilane, N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltriethoxysilane, 1,1,3,3-tetramethyl-2- [ 3- (Trimethylsilyl) propyl] guanidine.
- the curing catalyst including an organic compound having such a nitrogen atom can be used alone or in combination of two or more.
- the organic compound having a nitrogen atom not only functions as a curing catalyst for promoting the reaction between the hydroxyl group or alkoxy group of the component (a1) and the hydrolyzable group of the component (b1), but also functions as an adhesion promoter. Also have. Therefore, when the organic compound having a nitrogen atom is used as a curing catalyst, a cured product having excellent adhesion can be obtained.
- the total amount of component (b3) is 0.01 to 10 parts by weight, preferably 0.05 to 5 parts by weight, particularly preferably 0.05 to 3 parts by weight per 100 parts by weight of component (a1). . If it is less than 0.01 part by mass, not only will it take a long time to cure, but in particular the curing in the deep part of the rubber layer far from the contact surface with air will be insufficient. When the component (b3) exceeds 10 parts by mass, there is no effect commensurate with the blending amount, which is meaningless and economically disadvantageous. From the viewpoint of improving adhesiveness, the compounding amount of the amino group-containing alkoxysilane in the component (b3) is more preferably 0.1 to 5 parts by mass per 100 parts by mass of the component (a1). When this compounding quantity exceeds 5 mass parts, there exists a possibility that the rubber strength of hardened
- the room temperature curable polyorganosiloxane composition of the present invention comprises (A) a main agent composition containing the above-described (a1) component and (a2) inorganic filler, and (b1) component and (b2) component which are crosslinking agents. And (b3) prepared separately from (B) a crosslinking agent composition containing a curing catalyst, and stored separately in a state where moisture is blocked.
- (A) the main agent composition and (B) the cross-linking agent composition are mixed at an appropriate blending ratio and exposed to moisture in the air, so that a condensation reaction occurs and cures and becomes rubbery. A cured product having elasticity is obtained.
- the blending ratio (mass ratio) of (A) the main agent composition and (B) the crosslinking agent composition is preferably 100: 3 to 100: 20. Further, from the viewpoint of ease of measurement / mixing and ease of handling, it is preferable to blend (A) the main agent composition and (B) the crosslinking agent composition in an integer ratio. When the blending ratio is out of the above range and the mass ratio of the (B) crosslinking agent composition is too low, curing becomes insufficient and a cured product cannot be obtained.
- a more preferable blending ratio of (A) the main agent composition and (B) the crosslinking agent composition is 100: 5 to 100: 15.
- the composition of the present invention further includes a pigment, a thixotropy imparting agent, a viscosity modifier for improving extrusion workability, an ultraviolet absorber, a fungicide, a heat resistance improver, a flame retardant, depending on the purpose.
- Various additives may be added. These additives are usually added and mixed in the (A) main agent composition.
- the blending ratio of (A) the main agent composition and (B) the crosslinker composition can be appropriately adjusted according to the use of an automatic mixing / discharging machine or the like.
- part means “part by mass”, and all physical properties such as viscosity are values at 23 ° C. and relative humidity 50%.
- Example 1 Linear polydimethylsiloxane ( ⁇ , ⁇ -bis-dihydroxypolydimethylsiloxane) having a hydroxyl group at both ends with a viscosity of 3 Pa ⁇ s (number average degree of polymerization 320) (a1) (hydroxyl group content 0.05 mmol / g)
- a1 hydroxyl group content 0.05 mmol / g
- silica powder ROX200; trade name of Nippon Aerosil Co., Ltd.
- polydimethylsiloxane (b2-1) having a polymerization degree of 7 blocked at both ends with a methyldimethoxy group was mixed with a tetraethoxysilane partial hydrolysis condensate (polymerization degree 7, alkoxy group content of 19.2 mmol / g).
- B1-1) 2 parts, dibutyltin dilaurate (b3-1) 0.05 part, and N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane (b3-3) 1 part are added and mixed.
- a crosslinking agent composition was prepared.
- the hardness variation (III) of the cured product and the surface state (IV) of the cured product were examined as follows. Further, in order to know the storage stability of the (B) crosslinking agent composition, the (B) crosslinking agent composition placed in a glass bottle was aged in an oven at 70 ° C. for 5 days. Then, (V) the state of (B) component after aging (uniformity of composition) and (VI) the curability by (B) component after aging were examined. At that time, in the same manner as described above, it was filled in a polystyrene cup having a capacity of 25 ml and allowed to stand in an atmosphere of 23 ° C. and 50% RH for 24 hours to be cured, and then the cured state inside the obtained cured product was observed. .
- Example 2 the component of the composition shown in Table 1 and Table 2 was mixed like Example 1, and the (B) crosslinking agent composition was prepared.
- (b2-2) is a polydimethylsiloxane having a polymerization degree of 20 blocked at both ends with methyldimethoxy groups
- (b2-3) is a polydimethylsiloxane having a polymerization degree of 25 having both ends blocked by methyldimethoxy groups.
- Dimethylsiloxane (b2-4) is a polydimethylsiloxane having a polymerization degree of 80 blocked at both ends with methyldimethoxy groups, and (b2-5) is a polydimethylsiloxane containing 10 mol% of phenyl groups (viscosity 0.05 Pa ⁇ s), (b2-6) are linear polydimethylsiloxanes having a viscosity of 0.1 Pa ⁇ s, (b2-7) is the same ⁇ , ⁇ -bis-dihydroxypolydimethylsiloxane as (a1), (b2-8) Represents octamethylcyclotetrasiloxane, respectively.
- the (B) crosslinker composition prepared in Examples 1 to 5 has excellent uniformity of the initial components and excellent storage stability, and even after aging. There is no separation. Then, such (B) crosslinker composition is mixed with (A) main agent composition in an appropriate ratio, and left to stand in the air to cure at normal temperature. A cured product having no variation in thickness can be obtained.
- the (B) crosslinking agent composition containing aminopropyltriethoxysilane (b3-2) and N- ( ⁇ -aminoethyl) - ⁇ -aminopropyltrimethoxysilane (b3-3) According to the blended compositions of Examples 1 and 2 and Example 5, cured products having excellent adhesion to substrates such as metals such as Al and resins such as PPS can be obtained.
- the room temperature curable polyorganosiloxane composition of the present invention comprises two components, (A) a main agent composition and (B) a crosslinker composition, and the blending ratio of these components is adapted to the use of an automatic mixing / discharging machine or the like. It can be adjusted appropriately.
- the room temperature curable polyorganosiloxane composition of the present invention can be used as an elastic adhesive, a coating material, an electrical insulating sealing material, an architectural sealing material, etc. in the electric / electronic industry.
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Abstract
Description
(a1)成分
(a1)成分である分子末端に水酸基またはアルコキシ基を有するポリオルガノシロキサンは、通常室温で硬化し得る縮合型シリコーンゴムのベースポリマーとして用いられるものであり、直鎖状の構造を有するポリジオルガノシロキサンが好ましい。反応速度の観点から、分子末端に水酸基を有するポリオルガノシロキサンの使用がより好ましい。
(a2)成分である無機充填剤は、硬化後のゴム状弾性体に機械的強度や硬さを付与する目的で、(A)主剤組成物に配合される。公知の無機充填剤を使用することができ、例えば、シリカ粉末、微粉末マイカ粉、けいそう土、炭酸カルシウム、炭酸亜鉛、酸化鉄、酸化チタン、酸化亜鉛、粉砕石英、カーボンブラック等が挙げられる。1種を単独で用いても2種以上を混合して用いてもよい。特に、煙霧質シリカ(ヒュームドシリカ)、沈澱シリカ(湿式シリカ)、シリカエアロゲル、粉砕石英、溶融シリカのようなシリカ粉末の使用が望ましい。また、ポリジメチルシロキサン、オクタメチルシクロテトラシロキサン、ヘキサメチルジシラザン等の有機ケイ素化合物により、表面処理したシリカ粉末を用いてもよい。
(b1)加水分解性基を有する有機ケイ素化合物またはその部分加水分解物
(b1)成分である1分子中に3個以上の加水分解性基を有する有機ケイ素化合物またはその部分加水分解物は、前記した(a1)成分の架橋剤として作用するものあり、空気中の水分によって加水分解し、(a1)成分の水酸基(シラノール基)またはアルコキシ基と容易に縮合反応することにより硬化物を生成する。
本発明において、前記(b1)成分とともに(B)架橋剤組成物を構成する(b2)成分は、(B)架橋剤組成物中での(b1)成分を希釈し、(A)主剤組成物と(B)架橋剤組成物との配合比を、自動混合吐出機等の計量・混合に適した混合比に調整する働きをする成分である。
(b3)成分は、(a1)成分の水酸基またはアルコキシ基と(b1)成分の加水分解性基とが水分の存在下で反応するための硬化触媒である。このような硬化触媒としては、鉄オクトエート、マンガンオクトエート、亜鉛オクトエート、スズナフテート、スズカプリレート、スズオレートのようなカルボン酸金属塩;ジブチルスズジアセテート、ジブチルスズジオクトエート、ジブチルスズジラウレート、ジブチルスズジオレート、ジフェニルスズジアセテート、酸化ジブチルスズ、ジブチルスズジメトキサイド、ジブチルビス(トリエトキシシロキシ)スズ、ジオクチルスズジラウレートのような有機スズ化合物;テトラエトキシチタン、テトラプロポキシチタン、テトラブトキシチタン、1、3-プロポキシチタンビス(エチルアセチルアセテート)のようなアルコキシチタン類;アルミニウムトリスアセチルアセトナート、アルミニウムトリスエチルアセトアセテート、ジイソプロポキシアルミニウムエチルアセトアセテート、トリエトキシアルミニウムなどの有機アルミニウム化合物;ジルコニウムテトラアセチルアセトナート、テトライソプロポキシジルコニウム、テトラブトキシジルコニウム、トリブトキシジルコニウムアセチルアセトネート、トリブトキシジルコニウムステアレートなどの有機ジルコニウム化合物等が挙げられる。微量の存在で大きな触媒能を持つことから、有機スズ化合物およびアルコキシチタン類の使用が好ましい。深部硬化性に優れるため、有機スズ化合物がさらに好ましい。
(R4O)3Si-R5-NH-R6
で表されるアミノ基含有アルコキシシラン(アミノ基置換アルコキシシランともいう。)を使用することができる。
本発明の組成物には、さらに目的に応じて、顔料、チクソトロピー性付与剤、押し出し作業性を改良するための粘度調整剤、紫外線吸収剤、防かび剤、耐熱性向上剤、難燃化剤など、各種の添加剤を加えてもよい。これらの添加剤は、通常(A)主剤組成物中に添加され混合される。
粘度3Pa・s(数平均重合度320)の両末端に水酸基を有する直鎖状のポリジメチルシロキサン(α,ω-ビス-ジヒドロキシポリジメチルシロキサン)(a1)(水酸基含量0.05mモル/g)95部に、シラザンにより表面処理されたシリカ粉末(ROX200;日本アエロジル(株)の商品名)(a2)5部を加え、プラネタリーミキサーにより均一に混合した後、100℃、200mmHgで2時間加熱減圧混練を行い、均一な(A)主剤組成物を得た。
得られた(B)架橋剤組成物の混合の状態を観察した。各成分が均一に混合しているものを「均一」、成分の分離や白濁が見られるものを「不均一」、粘度の上昇が見られ流動性がなくなったものを「ゲル化」と評価した。なお、(B)成分調製の初期状態で「ゲル化」が見られたものについては、以後の評価を行わなかった。
(A)主剤組成物200gに対して、(B)架橋剤組成物を表1に示す配合比率になるように容量500mlのディスカップに計量し、直径5mmのガラス棒で1分間激しく撹拌した。その後減圧脱泡したものを、テフロン(登録商標)コーティング30×80×6mmの金型5個にそれぞれ流し入れ、23℃、50%RHで24時間放置して硬化させた。得られた5個の硬化物の硬さをそれぞれ硬度計(タイプE)により測定し、硬さの最大値と最小値との差を求めた。
前記(III)の測定で作製された硬化物の表面状態を観察し、オイルブリードの有無を調べた。そして、オイルブリードのないものを「良好」、オイルブリードが生じているものを「不良」と評価した。
(B)架橋剤組成物を50mlのガラス瓶に30g入れ、密閉後70℃のオーブンに5日間入れた後、状態を観察した。各成分が均一に混合しているものを「均一」、成分の分離や白濁が見られるものを「不均一」と評価した。
70℃で5日間エージングした後の(B)架橋剤組成物を使用し、前記と同様にして硬化物の深部硬化性を調べて評価した。これらの測定結果を表1に示す。
粘度3Pa・sのα,ω-ビス-ジヒドロキシポリジメチルシロキサン(水酸基含量0.05mモル/g)(a1-1)95部に、シラザンにより表面処理されたシリカ粉末(ROX200;日本アエロジル(株)の商品名)(a2)5部を加え、実施例1と同様に混練して(A)主剤組成物を調製した。
なお、表中の(b2-2)は両末端がメチルジメトキシ基で封鎖された重合度20のポリジメチルシロキサン、(b2-3)は両末端がメチルジメトキシ基で封鎖された重合度25のポリジメチルシロキサン、(b2-4)は両末端がメチルジメトキシ基で封鎖された重合度80のポリジメチルシロキサン、(b2-5)はフェニル基を10モル%含有するポリジメチルシロキサン(粘度0.05Pa・s)、(b2-6)は粘度0.1Pa・sの直鎖状ポリジメチルシロキサン、(b2-7)は(a1)と同じα,ω-ビス-ジヒドロキシポリジメチルシロキサン、(b2-8)はオクタメチルシクロテトラシロキサンをそれぞれ示している。
(A)主剤組成物と(B)架橋剤組成物とを表3に示す質量比で混合してなる組成物を、アルミニウム(JIS H4000合格品;1050P)基材とポリフェニレンサルファイド(PPS)基材およびポリブチレンテレフタレート(PBT)基材の上にそれぞれ塗布し、23℃、50%RHで7日間以上放置して硬化させた後、硬化物を基材から剥がして凝集破壊率を調べた。
Claims (6)
- (A)(a1)分子末端に水酸基またはアルコキシ基を有するポリオルガノシロキサンと、(a2)無機充填剤を含む主剤組成物と、
(B)(b1)1分子中にケイ素原子に結合した3個以上の加水分解性基を有する有機ケイ素化合物、またはその部分加水分解物と、(b2)一般式:
とを配合してなることを特徴とする室温硬化性ポリオルガノシロキサン組成物。 - 前記(a1)成分は、分子末端に水酸基を有するポリオルガノシロキサンであることを特徴とする請求項1記載の室温硬化性ポリオルガノシロキサン組成物。
- 前記(b3)硬化触媒として、窒素原子を含有する有機化合物を含有することを特徴とする請求項1記載の室温硬化性ポリオルガノシロキサン組成物。
- 前記(b3)硬化触媒として、一般式:(R4O)3Si-R5-NH-R6
(式中、R4は互いに同一であっても異なっていてもよい、アルキル基またはアルコキシアルキル基であり、R5は非置換の2価の炭化水素基であり、R6は水素原子、または非置換もしくはハロゲンまたはシアノ基で置換された1価の炭化水素基、またはアミノアルキル基である。)で示されるアミノ基含有アルコキシシランを含有することを特徴とする請求項3記載の室温硬化性ポリオルガノシロキサン組成物。 - 前記(A)主剤組成物が、前記(a1)成分100質量部に対して、前記(a2)無機充填剤を1~500質量部の割合で含み、かつ前記(a1)成分100質量部に対して、前記(b2)成分が0.5~20質量部、前記(b3)硬化触媒が0.01~10質量部となり、前記(a1)成分の水酸基またはアルコキシ基1個に対して、前記(b1)成分のアルコキシ基が2~20個となるように、前記(B)架橋剤組成物を配合してなることを特徴とする請求項1記載の室温硬化性ポリオルガノシロキサン組成物。
- 前記(A)主剤組成物と前記(B)架橋剤組成物とを、100:3~100:20の質量比で配合してなることを特徴とする請求項1記載の室温硬化性ポリオルガノシロキサン組成物。
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015067647A (ja) * | 2013-09-27 | 2015-04-13 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
CN105038689A (zh) * | 2015-07-03 | 2015-11-11 | 黑龙江省科学院石油化学研究院 | 一种无溶剂室温交联有机硅压敏胶及其制备方法 |
JP2020029525A (ja) * | 2018-08-23 | 2020-02-27 | 株式会社オリジン | 塗料組成物、塗装品及び塗装品の製造方法 |
WO2020203298A1 (ja) * | 2019-03-29 | 2020-10-08 | ダウ・東レ株式会社 | 室温硬化性オルガノポリシロキサン組成物および電気・電子部品の保護剤または接着剤組成物 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10231867B2 (en) | 2013-01-18 | 2019-03-19 | Auris Health, Inc. | Method, apparatus and system for a water jet |
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Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05331370A (ja) * | 1992-05-28 | 1993-12-14 | Toray Dow Corning Silicone Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
JPH07133430A (ja) | 1993-11-09 | 1995-05-23 | Toshiba Silicone Co Ltd | 室温硬化性ポリオルガノシロキサン組成物 |
JPH11209620A (ja) | 1998-01-20 | 1999-08-03 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
JP2006265529A (ja) * | 2005-02-28 | 2006-10-05 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
JP2008150491A (ja) * | 2006-12-18 | 2008-07-03 | Momentive Performance Materials Japan Kk | 室温硬化性ポリオルガノシロキサン組成物 |
JP2009292914A (ja) * | 2008-06-04 | 2009-12-17 | Momentive Performance Materials Inc | 室温硬化性シリコーンゴム組成物 |
JP2010084062A (ja) * | 2008-10-01 | 2010-04-15 | Momentive Performance Materials Inc | 室温硬化性オルガノポリシロキサン組成物 |
JP2010084063A (ja) * | 2008-10-01 | 2010-04-15 | Momentive Performance Materials Inc | 室温硬化性オルガノポリシロキサン組成物 |
JP2010120984A (ja) * | 2008-11-17 | 2010-06-03 | Momentive Performance Materials Inc | 電子部品封止用難燃性ポリオルガノシロキサン組成物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6534581B1 (en) * | 2000-07-20 | 2003-03-18 | Dow Corning Corporation | Silicone composition and electrically conductive silicone adhesive formed therefrom |
JP3714861B2 (ja) | 2000-09-20 | 2005-11-09 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
JP4088764B2 (ja) | 2002-07-01 | 2008-05-21 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
US20060089431A1 (en) * | 2004-10-25 | 2006-04-27 | Kaneka Corporation | Curable composition |
EP2021175A2 (en) * | 2006-04-18 | 2009-02-11 | Dow Corning Corporation | Metal foil substrates coated with condensation cured silicon resin compositions |
DE102007037198A1 (de) | 2007-08-07 | 2009-02-12 | Wacker Chemie Ag | Vernetzbare Massen auf der Basis von Organosiliciumverbindungen |
CN101945951B (zh) * | 2007-12-19 | 2015-07-29 | 迈图高新材料日本合同公司 | 室温固化性聚有机硅氧烷组合物 |
JP4984086B2 (ja) * | 2008-05-14 | 2012-07-25 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
JP2011042760A (ja) * | 2009-08-24 | 2011-03-03 | Nitto Denko Corp | 熱硬化性シリコーン樹脂用組成物 |
-
2012
- 2012-05-10 WO PCT/JP2012/003071 patent/WO2012157225A1/ja active Application Filing
- 2012-05-10 JP JP2012523543A patent/JP5265813B2/ja active Active
- 2012-05-10 EP EP12786117.7A patent/EP2708579B1/en active Active
- 2012-05-10 CN CN201280004452.6A patent/CN103328576B/zh active Active
- 2012-05-10 KR KR1020137013338A patent/KR101866595B1/ko active IP Right Grant
-
2013
- 2013-06-27 US US13/928,820 patent/US9034993B2/en active Active
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH05331370A (ja) * | 1992-05-28 | 1993-12-14 | Toray Dow Corning Silicone Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
JPH07133430A (ja) | 1993-11-09 | 1995-05-23 | Toshiba Silicone Co Ltd | 室温硬化性ポリオルガノシロキサン組成物 |
JPH11209620A (ja) | 1998-01-20 | 1999-08-03 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
JP2006265529A (ja) * | 2005-02-28 | 2006-10-05 | Shin Etsu Chem Co Ltd | 室温硬化性オルガノポリシロキサン組成物 |
JP2008150491A (ja) * | 2006-12-18 | 2008-07-03 | Momentive Performance Materials Japan Kk | 室温硬化性ポリオルガノシロキサン組成物 |
JP2009292914A (ja) * | 2008-06-04 | 2009-12-17 | Momentive Performance Materials Inc | 室温硬化性シリコーンゴム組成物 |
JP2010084062A (ja) * | 2008-10-01 | 2010-04-15 | Momentive Performance Materials Inc | 室温硬化性オルガノポリシロキサン組成物 |
JP2010084063A (ja) * | 2008-10-01 | 2010-04-15 | Momentive Performance Materials Inc | 室温硬化性オルガノポリシロキサン組成物 |
JP2010120984A (ja) * | 2008-11-17 | 2010-06-03 | Momentive Performance Materials Inc | 電子部品封止用難燃性ポリオルガノシロキサン組成物 |
Non-Patent Citations (1)
Title |
---|
See also references of EP2708579A4 |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2015067647A (ja) * | 2013-09-27 | 2015-04-13 | 信越化学工業株式会社 | 室温硬化性オルガノポリシロキサン組成物 |
CN105038689A (zh) * | 2015-07-03 | 2015-11-11 | 黑龙江省科学院石油化学研究院 | 一种无溶剂室温交联有机硅压敏胶及其制备方法 |
CN105038689B (zh) * | 2015-07-03 | 2018-05-11 | 黑龙江省科学院石油化学研究院 | 一种无溶剂室温交联有机硅压敏胶及其制备方法 |
JP2020029525A (ja) * | 2018-08-23 | 2020-02-27 | 株式会社オリジン | 塗料組成物、塗装品及び塗装品の製造方法 |
WO2020203298A1 (ja) * | 2019-03-29 | 2020-10-08 | ダウ・東レ株式会社 | 室温硬化性オルガノポリシロキサン組成物および電気・電子部品の保護剤または接着剤組成物 |
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JPWO2012157225A1 (ja) | 2014-07-31 |
US20130303676A1 (en) | 2013-11-14 |
CN103328576B (zh) | 2016-03-09 |
CN103328576A (zh) | 2013-09-25 |
US9034993B2 (en) | 2015-05-19 |
KR20140045294A (ko) | 2014-04-16 |
EP2708579B1 (en) | 2016-04-27 |
EP2708579A4 (en) | 2014-11-26 |
JP5265813B2 (ja) | 2013-08-14 |
KR101866595B1 (ko) | 2018-06-11 |
EP2708579A1 (en) | 2014-03-19 |
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