WO2016117206A1 - 室温硬化性オルガノポリシロキサン組成物 - Google Patents
室温硬化性オルガノポリシロキサン組成物 Download PDFInfo
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Definitions
- the present invention relates to a room temperature curable organopolysiloxane composition, and more particularly to a room temperature curable organopolysiloxane composition that is cured and becomes a silicone rubber having excellent adhesion, and various articles using the cured product of the composition.
- An organopolysiloxane composition that cures at room temperature to become a silicone rubber (elastomer-like elastic body) has been conventionally known and has been widely used in the industry.
- the mechanisms for curing these organopolysiloxane compositions at room temperature include a mechanism for curing by hydrosilylation reaction, a mechanism for curing by ultraviolet light, and a mechanism for curing by a condensation reaction between a hydrolyzable group bonded to a silicon atom and a hydroxyl group. It has been known.
- an organopolysiloxane composition that cures by a condensation reaction can be easily cured at room temperature to give a rubber-like elastic body (silicone rubber), and also inhibits curing by impurities that occur in hydrosilylation reactions. It has the advantage of being difficult to do. Therefore, organopolysiloxane compositions that cure by a condensation reaction at room temperature are widely used in fields such as in-vehicle gaskets, sealing materials, architectural sealants, and electrical / electronic components.
- Silicone rubber When used in these applications, one important factor is the adhesion between the cured silicone rubber and the substrate and its water immersion adhesion. Silicone rubber is used in various outdoor applications because of its weather resistance and high chemical stability. However, silicone rubber has poor adhesion to various base materials, and in order to improve the adhesion of room temperature curable silicone rubber, a wide range of techniques for adding silane compounds having amino groups, epoxy groups, methacryl groups, mercapto groups, etc. It is used.
- amino group-containing alkoxysilane compounds include ⁇ -aminopropyltriethoxysilane, ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropylmethyldimethoxysilane, ⁇ -aminopropylmethyldiethoxysilane, N- ⁇ -aminoethyl.
- Patent Document 1 - ⁇ -aminopropylmethyldimethoxysilane, N-benzyl- ⁇ -aminopropyltrimethoxysilane, N-phenyl- ⁇ -aminopropyltrimethoxysilane, ⁇ -aminoethylaminomethylphenethyltrimethoxysilane, N- [m-amino Methylphenylmethyl] - ⁇ -aminopropyltrimethoxysilane and the like are known (Patent Document 1).
- epoxy group-containing alkoxysilane compounds examples include 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, and 3-glycidoxy.
- Propyltriethoxysilane and the like are known (Patent Document 2).
- methacryl group-containing alkoxysilane compounds include 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, and 3-methacryloxypropylmethyldiethoxysilane. (Patent Document 3).
- mercapto group-containing alkoxysilane compounds include 3-mercaptopropyltrimethoxysilane and 3-mercaptopropylmethyldimethoxysilane (Patent Document 4).
- Patent Document 4 a large number of alkoxysilane compounds have already been used as adhesion aids, but demands for improvement in adhesion to a substrate and in water-immersion adhesion are increasing year by year.
- the present invention has good workability in an uncured state and is cured to be used for general-purpose resins (acrylic (AC) resin, polybutylene terephthalate (PBT) resin, polycarbonate (PC) resin, acrylonitrile-butadiene-styrene). It is an object of the present invention to provide a room temperature-curable organopolysiloxane composition that gives a cured silicone rubber having good adhesion to (ABS) resin) and metals (aluminum, copper, stainless steel) and water-immersion adhesion.
- ABS room temperature-curable organopolysiloxane composition
- the present invention provides the following room temperature curable organopolysiloxane composition and various articles using the cured product (silicone rubber) of the composition.
- Z 1 is a divalent hydrocarbon group represented by C d H 2d (d represents an integer of 5 to 13). Curable organopolysiloxane composition.
- ⁇ 4> The room temperature-curable organopolysiloxane according to any one of ⁇ 1> to ⁇ 3>, wherein the component (C) is a silane compound represented by the following general formula (4) and / or a partial hydrolysis condensate thereof: Composition. (R'O) 3-c R 3 c Si-C 8 H 16 -NH-C 2 H 4 -NH 2 (4) (In the formula (4), c is an integer of 0 to 2, R′O is a hydrolyzable group, and R 3 is a substituted or unsubstituted monovalent hydrocarbon group.)
- ⁇ 6> An electrical component or electronic component having a cured product of the room temperature-curable organopolysiloxane composition according to any one of ⁇ 1> to ⁇ 4>.
- ⁇ 7> A building structure or a civil engineering structure having a cured product of the room temperature-curable organopolysiloxane composition according to any one of ⁇ 1> to ⁇ 4>.
- the room temperature curable organopolysiloxane composition of the present invention comprises a general-purpose resin (acrylic (AC) resin, polybutylene terephthalate (PBT) resin, polycarbonate (PC) resin, acrylonitrile-butadiene-styrene (ABS) resin) and metal (aluminum). , Copper, stainless steel) and a silicone rubber cured product (elastomer-like organopolysiloxane cured product) having good adhesion to water and water immersion.
- acrylic (AC) resin, polybutylene terephthalate (PBT) resin, polycarbonate (PC) resin, acrylonitrile-butadiene-styrene (ABS) resin acrylonitrile-butadiene-styrene (ABS) resin
- metal aluminum
- room temperature or “room temperature” usually means a temperature of 23 ° C. ⁇ 10 ° C., a humidity of 50% RH ⁇ 10% RH, particularly a temperature of 23 ° C. ⁇ 5 ° C., and a humidity of 50% RH ⁇ 5%. Refers to the state of RH.
- the component (A) is a diorganopolysiloxane having a hydroxyl group bonded to a silicon atom (that is, a silanol group) and / or a hydrolyzable group at both ends of the molecular chain, and the main component of the organopolysiloxane composition of the present invention ( Base polymer).
- the molecular structure of the diorganopolysiloxane is not particularly limited, and may be any of a straight chain, a branched chain, and a straight chain having a branched structure.
- silyl group and / or hydrolyzable silyl group (for example, diorganohydroxysilyl group and / or 1 to 3 hydrolyzed groups) consisting of repeating diorganosiloxane units and having both ends of the molecular chain bonded to silicon atoms It is a linear diorganopolysiloxane blocked with a triorganosilyl group containing a functional group (diorganoalkoxysilyl group, organodialkoxysilyl group, trialkoxysilyl group, etc.).
- the linear diorganopolysiloxane may have a small amount of a branched structure.
- the diorganopolysiloxane is present in the molecular chain (particularly, the connection between the silanol group and / or hydrolyzable silyl group at both ends of the molecular chain and the repeating structure of the diorganosiloxane unit constituting the main chain). It may have a silalkylene structure (—SiRSi—) or the like.
- R is a divalent hydrocarbon group having 1 to 20, preferably 2 to 6 carbon atoms (for example, a linear or branched alkylene group).
- part or all of the hydrogen atoms bonded to the carbon atom may be substituted with a halogen atom or a cyano group.
- the diorganopolysiloxane of component (A) has a viscosity at 25 ° C. of 20 to 1,000,000 mPa ⁇ s, preferably 100 to 300,000 mPa ⁇ s, more preferably 1,000 to 200,000 mPa ⁇ s, In particular, a material having a viscosity of 10,000 to 100,000 mPa ⁇ s is preferable.
- the viscosity of the diorganopolysiloxane is less than the lower limit (20 mPa ⁇ s), a large amount of the component (B) described later is required, which is economically disadvantageous.
- the viscosity of the diorganopolysiloxane exceeds the above upper limit (1,000,000 mPa ⁇ s), workability deteriorates, which is not preferable.
- the viscosity is measured with a rotational viscometer (for example, BL type, BH type, BS type, cone plate type, rheometer, etc.).
- the hydrolyzable group possessed by the (A) component diorganopolysiloxane is preferably an alkoxy group or an alkoxy-substituted alkoxy group.
- the number of hydroxyl groups (silanol groups) and hydrolyzable groups present at each end of the diorganopolysiloxane is not particularly limited.
- an alkoxy group bonded to a silicon atom that is, an alkoxysilyl group
- an alkoxy substituent bonded to a silicon atom at both ends of the molecular chain Two or three alkoxy groups (that is, alkoxyalkoxysilyl groups) (that is, dialkoxyorganosilyl groups or bis (alkoxyalkoxy) organosilyl groups, trialkoxysilyl groups, or tris (alkoxyalkoxy) silyl groups Present).
- the alkoxy group is preferably an alkoxy group having 1 to 10 carbon atoms, particularly 1 to 4 carbon atoms.
- the alkoxy-substituted alkoxy group is preferably an alkoxy-substituted alkoxy group having 2 to 10 carbon atoms, particularly 3 or 4 carbon atoms, and examples thereof include a methoxymethoxy group, a methoxyethoxy group, and an ethoxymethoxy group.
- Examples of the organic group bonded to the silicon atom other than the hydroxyl group and the hydrolyzable group include substituted or unsubstituted monovalent hydrocarbon groups having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms.
- Examples of the monovalent hydrocarbon group include alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, hexyl group, heptyl group, octyl group, and 2-ethylhexyl group.
- cycloalkyl groups such as cyclopentyl and cyclohexyl groups; alkenyl groups such as vinyl and allyl groups; aryl groups such as phenyl, tolyl and naphthyl groups; aralkyl groups such as benzyl, phenylethyl and phenylpropyl
- halogen atoms such as fluorine, bromine, chlorine or cyano groups
- halogenated compounds such as trifluoropropyl groups and chloropropyl groups
- cyanoalkyl groups such as ⁇ -cyanoethyl group and ⁇ -cyanopropyl group.
- a methyl group is preferred.
- the (A) diorganopolysiloxane is particularly preferably a compound represented by the following general formula (1).
- R 1 s are independently of each other a hydrogen atom; an alkyl group having 1 to 10 carbon atoms such as a methyl group, an ethyl group, a propyl group, a butyl group, and an octyl group; a methoxymethyl group, a methoxy group A group selected from an alkoxyalkyl group having 2 to 10 carbon atoms such as an ethyl group and an ethoxymethyl group.
- they are a hydrogen atom, a methyl group, or an ethyl group.
- R 2 is, independently of each other, a substituted or unsubstituted monovalent hydrocarbon group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms.
- the monovalent hydrocarbon group include organic groups other than the hydroxyl groups and hydrolyzable groups described above, and among them, a methyl group is preferable.
- a is 0, 1 or 2.
- n or degree of polymerization
- n or degree of polymerization
- a polymerization degree or molecular weight
- Y independently represents an oxygen atom, an unsubstituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, or the following general formula (2 ).
- R 2 is as in the above formula (1), and Z is an unsubstituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms.
- the divalent hydrocarbon group (Y or Z) may be linear or have a branched structure (for example, a methylethylene group), particularly a methylene group, an ethylene group, a propylene group (trimethylene group), A linear alkylene group such as a butylene group (tetramethylene group) or a hexylene group (hexamethylene group) is preferred. Among these, an ethylene group is particularly preferable.
- Y is an oxygen atom.
- the diorganopolysiloxane of the component (A) can be produced by a conventionally known method. These diorganopolysiloxanes may be used singly or in combination of two or more.
- diorganopolysiloxane having hydroxysilyl groups at both ends of the molecular chain that is, diorganopolysiloxane in which R 1 at both ends in the above formula (1) is a hydrogen atom
- the content is preferably 10 to 100 parts by mass, and more preferably 50 to 100 parts by mass.
- the component (A) is preferably contained in an amount of 99 to 20% by mass, particularly preferably 95 to 50% by mass, in the room temperature curable organopolysiloxane composition of the present invention.
- Component (B) is a hydrolyzable organosilane compound and / or a partially hydrolyzed condensate thereof having three or more hydrolyzable groups bonded to silicon atoms in the molecule (that is, three residual hydrolyzable groups).
- a siloxane compound such as a siloxane oligomer.
- Component (B) is a crosslink in which three or more hydrolyzable groups in the molecule form a crosslinked structure by a hydrolysis / condensation reaction with the terminal silanol group and / or hydrolyzable silyl group in component (A). It acts as an agent (curing agent).
- the component (B) is a compound different from the component (A) and the component (C) described later.
- the component (B) is differentiated from the component (A) in that it does not essentially contain a repeating structure composed of a bifunctional diorganosiloxane unit in the molecule.
- the component B) is clearly different from the component (C) described later in that the component does not contain a nitrogen atom bonded to a silicon atom via a divalent hydrocarbon group having 5 or more carbon atoms in the molecule. It will be
- the hydrolyzable group possessed by the hydrolyzable organosilane compound or organosiloxane (partially hydrolyzed condensate, etc.) of the component (B) includes an alkoxy group, an alkoxy-substituted alkoxy group, an acyloxy group having 1 to 10 carbon atoms in total. Groups, alkenoxy groups, ketoxime groups, aminoxy groups, and amide groups.
- alkoxy groups such as methoxy group, ethoxy group and propoxy group
- alkoxy-substituted alkoxy groups such as methoxyethoxy group, ethoxyethoxy group and methoxypropoxy group
- acyloxy groups such as acetoxy group and octanoyloxy group
- Alkenoxy groups such as 1-ethyl-2-methylvinyloxy group
- ketoxime groups such as dimethyl ketoxime group, methyl ethyl ketoxime group and methyl isobutyl ketoxime group
- aminoxy groups such as dimethylaminoxy group and diethylaminoxy group
- N— Examples include amide groups such as methylacetamide group and N-ethylacetamide group.
- Examples of the organic group bonded to a silicon atom other than the hydrolyzable group include substituted or unsubstituted monovalent hydrocarbon groups having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms.
- alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, octadecyl, etc.
- a cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; an alkenyl group such as a vinyl group and an allyl group; an aryl group such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group; a benzyl group, a phenethyl group, and a phenylpropyl group Aralkyl groups; those in which some or all of the hydrogen atoms bonded to the carbon atoms of these groups are substituted with halogen atoms such as fluorine, bromine, chlorine, or cyano groups, such as 3-chloropropyl groups, 3, 3, 3 -Halogenated alkyl groups such as a trifluoropropyl group.
- halogen atoms such as fluorine, bromine, chlorine, or cyano groups, such as 3-chloropropyl groups, 3, 3, 3 -
- silane compound (B) examples include methyltrimethoxysilane, ethyltrimethoxysilane, decyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, ethyltriethoxysilane, and vinyltriethoxy.
- Alkoxysilanes such as silane, phenyltriethoxysilane, tetramethoxysilane, tetraethoxysilane; methyltris (dimethylketoxime) silane, methyltris (methylethylketoxime) silane, ethyltris (methylethylketoxime) silane, methyltris (methylisobutylketoxime) silane, Ketoxime silanes such as vinyltris (methylethylketoxime) silane; methyltri (methoxymethoxy) silane, ethyltri (methoxy Toxi) silane, vinyltri (methoxymethoxy) silane, phenyltri (methoxymethoxy) silane, methyltri (ethoxymethoxy) silane, ethyltri (ethoxymethoxy) silane, vinyltri (ethoxymethoxy) silane, phenyltri (methoxyme
- siloxane compound of a component As a siloxane compound of a component, the partial hydrolysis-condensation product of the said silane compound is mentioned.
- the mass average molecular weight (or mass average polymerization degree) of the siloxane is not particularly limited, but is preferably an oligomer in which 2 to 100, preferably 2 to 20, silane compounds are polymerized.
- the siloxane may be a mixture of oligomers having a plurality of polymerization degrees.
- a component may be used individually by 1 type or in combination of 2 or more types. Moreover, you may use together the silane compound and / or siloxane which have two hydrolyzable groups in 1 molecule in the range which does not prevent the effect of this invention.
- the amount of the component (B) is 0.1 to 40 parts by mass, preferably 1 to 20 parts by mass with respect to 100 parts by mass of the component (A). If the amount of the component (B) is less than the lower limit (0.1 part by mass), the curability and storage stability may be lowered. Moreover, when the said upper limit (40 mass parts) is exceeded, there exists a possibility that not only it may become disadvantageous in price, but the elongation of hardened
- the component (A) contains a diorganopolysiloxane having a hydroxyl group at the terminal, such an amount that the number of hydrolyzable groups in the component (B) exceeds the number of hydroxyl groups in the component (A) It is preferable to do.
- Component (C) has a hydrolyzable group and two nitrogen atoms in the molecule other than the components (A) and (B), and one nitrogen atom has 5 carbon atoms.
- a hydrolyzable silane compound and / or a partially hydrolyzed condensate thereof (a siloxane compound such as a siloxane oligomer) which is bonded to a silicon atom via the above divalent hydrocarbon group.
- component (C) is usually present in the middle or at the end of the same monovalent organic group (substituted monovalent hydrocarbon group) bonded to the silicon atom, Among them, the nitrogen atom closer to the silicon atom is bonded to the silicon atom via a divalent hydrocarbon group having 5 or more carbon atoms.
- Component (C) is a cured product (silicone rubber) of the room temperature curable organopolysiloxane composition of the present invention with excellent (initial) adhesion and water immersion adhesion to various substrates (particularly difficult-to-adhere substrates). It is an important component in expressing sex.
- the room temperature curable organopolysiloxane composition of the present invention is cured to a general-purpose resin (acrylic (AC) resin, polybutylene terephthalate (PBT) resin, polycarbonate (PC) resin, acrylonitrile-butadiene-styrene (ABS) resin) and It is presumed that the component (C) contributes greatly to the fact that it adheres well to metals (aluminum, copper, stainless steel) and has good submerged adhesion. The reason is that one of the two nitrogen atoms in the molecule is bonded to a silicon atom via a divalent hydrocarbon group having 5 or more carbon atoms.
- AC acrylic
- PBT polybutylene terephthalate
- PC polycarbonate
- ABS acrylonitrile-butadiene-styrene
- the component (C) is an important component of the present invention as an adhesion improver (adhesion promoter).
- component (C) two nitrogen atoms present in the molecule are linked to each other by an unsubstituted or substituted divalent hydrocarbon group (for example, a linear or branched alkylene group).
- an unsubstituted or substituted divalent hydrocarbon group for example, a linear or branched alkylene group.
- the above (C) is more preferably a hydrolyzable silane compound represented by the following general formula (3), particularly a hydrolyzable silane compound represented by the following general formula (4).
- R′O 3-c R 3 c Si—Z 1 —NH—Z 2 —NH 2
- R'O 3-c R 3 c Si-C 8 H 16 -NH-C 2 H 4 -NH 2 (4)
- R′O is a hydrolyzable group, an alkoxy group having 1 to 10, preferably 1 to 6, more preferably 1 to 4 carbon atoms, Examples include alkoxy-substituted alkoxy groups, acyloxy groups, alkenoxy groups, ketoxime groups, aminoxy groups and amide groups.
- an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a tert-butoxy group; an alkoxy-substituted alkoxy group such as a methoxyethoxy group, an ethoxyethoxy group, and a methoxypropoxy group; an acetoxy group
- An acyloxy group such as octanoyloxy group; an alkenoxy group such as vinyloxy group, allyloxy group, propenoxy group, isopropenoxy group, 1-ethyl-2-methylvinyloxy group; dimethyl ketoxime group, methyl ethyl ketoxime group, methyl isobutyl ketoxime And ketoxime groups such as groups.
- an alkoxy group and a ketoxime group are preferable, an alkoxy group is more preferable, and a methoxy group or an ethoxy group
- R 3 is a substituted or unsubstituted monovalent group having 1 to 18 carbon atoms, preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
- a hydrocarbon group is mentioned.
- alkyl such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, octadecyl, etc.
- a cycloalkyl group such as a cyclopentyl group and a cyclohexyl group; an alkenyl group such as a vinyl group and an allyl group; an aryl group such as a phenyl group, a tolyl group, a xylyl group, and a naphthyl group; a benzyl group, a phenethyl group, and a phenylpropyl group Aralkyl groups; those in which some or all of the hydrogen atoms bonded to the carbon atoms of these groups are substituted with halogen atoms such as fluorine, bromine, chlorine, or cyano groups, such as 3-chloropropyl groups, 3, 3, 3 -Halogenated alkyl groups such as a trifluoropropyl group.
- halogen atoms such as fluorine, bromine, chlorine, or cyano groups
- substituted or unsubstituted monovalent hydrocarbon group a methyl group, an ethyl group, a propyl group, a vinyl group, and a phenyl group are preferable.
- c is an integer of 0 to 2, and 0 or 1 is preferable among them.
- Z 1 is an unsubstituted or substituted divalent hydrocarbon group having 5 or more carbon atoms, particularly 5 to 13 carbon atoms.
- the divalent hydrocarbon group may be linear or branched, but is preferably an alkylene group, represented by C d H 2d (d represents an integer of 5 to 13).
- pentylene group pentamethylene group
- hexylene group hexamethylene group
- heptylene group heptamethylene group
- octylene group octamethylene group
- nonylene group nonamethylene group
- decylene group decamethylene group
- an undecylene group (undecamethylene group), a dodecylene group (dodecamethylene group), a tridecylene group (dridecamethylene group) and the like are preferable.
- an octylene group, a nonylene group, a decylene group, and an undecylene group are preferable.
- Z 2 is an unsubstituted or substituted divalent hydrocarbon group having 1 to 20 carbon atoms, preferably 1 to 6 carbon atoms, more preferably 2 to 4 carbon atoms.
- the divalent hydrocarbon group may be linear or have a branched structure, but is preferably an alkylene group, particularly a methylene group, ethylene group, propylene group (trimethylene group), butylene group ( Tetramethylene group) and hexylene group (hexamethylene group) are preferable.
- an ethylene group, a propylene group (trimethylene group), and a butylene group (tetramethylene group) are preferable.
- the amount of component (C) is 0.001 to 10 parts by weight, preferably 0.01 to 7 parts by weight, and more preferably 0.05 to 5 parts by weight with respect to 100 parts by weight of component (A). Most preferably, it is 0.2 to 2 parts by mass.
- amount of component (C) is less than the lower limit (0.001 part by mass)
- desired adhesiveness cannot be obtained.
- the amount of the component (C) exceeds the above upper limit (10 parts by mass), not only is it disadvantageous in price, but there is a possibility that the elongation of the composition is lowered, the water resistance is lowered, or the durability is deteriorated. is there.
- (C) As a silane compound of a component, as what is represented by the said Formula (3), for example, N-2- (aminoethyl) -5-aminopentyltrimethoxysilane, N-2- (aminoethyl) -6-aminohexyltrimethoxysilane, N-2- (aminoethyl) -7-aminoheptyltrimethoxysilane, N-2- (aminoethyl) -8-aminooctyltrimethoxysilane, N-2- (aminoethyl) -9-aminononyltrimethoxysilane, N-2- (aminoethyl) -10-aminodecyltrimethoxysilane, N-2- (aminoethyl) -11-aminoundecyltrimethoxysilane, N-2- (aminoethyl) -12-amin
- a curing catalyst is preferably added to the composition of the present invention as the component (D) as necessary.
- a condensation catalyst is preferable.
- a condensation catalyst conventionally used as a curing accelerator for a room temperature-curable organopolysiloxane composition such as dibutyltin methoxide, dibutyltin diacetate, dibutyltin dioctate, Organotin compounds such as dibutyltin dilaurate, dioctyltin dilaurate, dioctyltin dioctate, dimethyltin dimethoxide, dimethyltin diacetate; tetrapropyl titanate, tetrabutyl titanate, tetra-2-ethylhexyl titanate, dimethoxy titanium diacetylacetonate, etc.
- Organic titanium compounds such as hexylamine, 3-aminopropyltrimethoxysilane, tetramethylguanidylpropyltrimethoxysilane, and the like, and salts thereof. Is, it is possible to use these alone or in combination of two or more.
- the amount thereof is 0.001 to 20 parts by mass, preferably 0.005 to 5 parts by mass, more preferably 0.01 to 100 parts by mass with respect to 100 parts by mass of the component (A). 2 parts by mass.
- the amount of the component (D) is less than the above lower limit value, the catalytic effect may not be obtained, and when the amount of the component (D) exceeds the above upper limit value, not only is it disadvantageous in price, The durability of the composition may deteriorate, or the adhesiveness may deteriorate.
- additives generally known for resin compositions may be added as optional components as long as the effects of the present invention are not impaired.
- the additive include dry silica (fumed silica or fumed silica), wet silica (precipitated silica), sol-gel silica, colloidal silica, fused silica (spherical silica), crystalline silica (quartz fine powder) ) And other silica-based fillers, colloidal calcium carbonate, heavy (or pulverized) calcium carbonate, quartz fine powder, diatomaceous earth powder, aluminum hydroxide powder, particulate alumina, magnesia powder, zinc oxide powder, and silane Fine powdery inorganic fillers surface-treated with polysiloxanes, silazanes, low-polymerization polysiloxanes, etc .; coloring agents such as pigments, dyes, fluorescent brighteners;
- the cured silicone rubber obtained by curing the room temperature-curable organopolysiloxane composition of the present invention is a general-purpose resin (acrylic (AC) resin, polybutylene terephthalate (PBT) resin, polycarbonate (PC) resin, acrylonitrile-butadiene-styrene). (ABS) resin) and metal (aluminum, copper, stainless steel) and excellent in water adhesion. Therefore, the room temperature curable organopolysiloxane composition of the present invention is useful as an adhesive, a sealing material, a potting agent or a coating agent.
- AC acrylic
- PBT polybutylene terephthalate
- PC polycarbonate
- ABS acrylonitrile-butadiene-styrene
- a method of using the organopolysiloxane composition of the present invention as an adhesive, a sealing material, a potting agent or a coating agent may be a conventionally known method.
- the target articles include automobile parts, automobile oil seals, electric / electronic parts, electric wires / cables, construction structures, civil engineering structures, and the like.
- Example and a comparative example are shown and this invention is demonstrated in detail, this invention is not restrict
- all the parts in an Example mean a mass part.
- the viscosity is a value measured at 25 ° C. by a rotational viscometer according to the method specified in JIS Z 8803.
- A Component (A-1) Hydroxydimethylsiloxy group-blocked polydimethylsiloxane having both hydroxyl groups bonded to silicon atoms (silanol groups) at both ends of the molecular chain (made by Shin-Etsu Chemical Co., Ltd.) , Viscosity 50,000 mPa ⁇ s)
- B Component (B-1) Methyltrimethoxysilane (B-2) Methyltris (methylethylketoxime) silane (B-3) Vinyltriisopropenoxysilane
- (C-1) is obtained by dehydrohalogenation reaction between ethylenediamine and 5-bromopentyltrimethoxysilane
- (C-3) is obtained by dehydrohalogenation reaction between ethylenediamine and 11-bromoundecyltrimethoxysilane. Synthesized.
- the reaction may be carried out under known reaction conditions. Specifically, the reaction product can be obtained by heating and stirring.
- E-1 Hemitic silica (trade name: MU-215, dimethyldichlorosilane surface hydrophobized product, BET specific surface area: 120 m 2 / g, water content 0.5 mass%, manufactured by Shin-Etsu Chemical Co., Ltd.)
- Example 1 100 parts of molecular chain-terminated hydroxydimethylsiloxy group-blocked polydimethylsiloxane (A-1) each having one hydroxyl group (silanol group) bonded to a silicon atom at both ends of the molecular chain, and 10 parts of fumed silica (E) are uniformly mixed, and 5 parts of (B-1), 1 part of (C-1) and 0.1 part of (D-1) are sequentially added and mixed uniformly to obtain a room temperature curable organopolysiloxane composition. A product was prepared. The mixing was performed using a universal mixer.
- Examples 2 to 12 A room temperature curable organopolysiloxane composition having the composition shown in Table 1 was prepared in the same manner as in Example 1.
- Adhesion test About each composition obtained above, adhesiveness was evaluated by the method shown below. Each of the above compositions was applied on the adherend to a thickness of about 2 mm and allowed to stand at room temperature for 7 days. Then, the simple adhesiveness test pulled by hand was implemented. Further, the same simple adhesion test was carried out even when immersed in water at 40 ° C. for 7 days after standing at room temperature for 7 days. The case where the fracture state after pulling was cohesive failure was evaluated as good ( ⁇ ), and the case where it was adhesive failure (interfacial separation at the adhesive surface) was evaluated as defective (x).
- the adhesion improver has two nitrogen atoms in a molecule such as (C-1), (C-2), and (C-3), and one of the nitrogen atoms is
- a hydrolyzable silane compound as the component (C) of the present invention which is bonded to a silicon atom via a divalent hydrocarbon group having 5 or more carbon atoms, is blended, these compositions are cured.
- the cured silicone rubber obtained showed excellent adhesion to all the adherends tested this time both at room temperature 7 days and at 40 ° C. after 7 days of immersion [Examples 1 to 12].
- the nitrogen atom is not contained even if the molecule has two nitrogen atoms such as (C-4) and (C-5).
- a conventional adhesion improver such as a silane compound bonded to a silicon atom via a divalent hydrocarbon group having 3 carbon atoms, or a silane compound having only one nitrogen atom in the molecule is blended. In some cases, adhesion to various adherends was poor, and the result was that the adherend peeled off many adherends after the water immersion test [Comparative Examples 1 to 9].
- the product of the present invention can be used for general-purpose resins (acrylic (AC) resin, polybutylene terephthalate (PBT) resin, polycarbonate (PC) resin, acrylonitrile-butadiene-styrene (ABS) resin) and metals (aluminum, copper, stainless steel).
- AC acrylic
- PBT polybutylene terephthalate
- PC polycarbonate
- ABS acrylonitrile-butadiene-styrene
- metals aluminum, copper, stainless steel
- the organopolysiloxane composition of the present invention is useful as an adhesive, a sealing material, a potting agent, a coating agent, and the like, and in particular, an automobile part or an automobile oil seal, an electrical part or an electronic part, and an architectural use. It can be suitably used as an adhesive for structures or civil engineering structures.
Abstract
Description
従って、本発明は、未硬化の状態で作業性が良好であると共に、硬化して汎用樹脂(アクリル(AC)樹脂、ポリブチレンテレフタレート(PBT)樹脂、ポリカーボネート(PC)樹脂、アクリロニトリル-ブタジエン-スチレン(ABS)樹脂)及び金属(アルミニウム、銅、ステンレス)への接着性及び浸水接着性が良好なシリコーンゴム硬化物を与える、室温硬化性オルガノポリシロキサン組成物を提供することを目的とする。
(A)ケイ素原子に結合した水酸基及び/又は加水分解性基を分子鎖両末端に有し、25℃における粘度が20~1,000,000mPa・sであるジオルガノポリシロキサン:100質量部、
(B)(A)成分以外の、ケイ素原子に結合した加水分解性基を分子中に3個以上有する加水分解性シラン化合物及び/又はその部分加水分解縮合物:(A)成分100質量部に対して0.1~40質量部、並びに
(C)(A)成分及び(B)成分以外の、分子中に加水分解性基及び2個の窒素原子を有し、かつ、その内1個の窒素原子が炭素原子数5個以上の二価炭化水素基を介してケイ素原子に結合したものである、加水分解性シラン化合物及び/又はその部分加水分解縮合物:(A)成分100質量部に対して0.001~10質量部
を含有する室温硬化性オルガノポリシロキサン組成物。
(C)成分が、下記一般式(3)で示されるシラン化合物及び/又はその部分加水分解縮合物である〈1〉記載の室温硬化性オルガノポリシロキサン組成物。
(R’O)3-c R3 c Si-Z1 -NH-Z2 -NH2 (3)
(式(3)中、cは、0~2の整数であり、R’Oは加水分解性基であり、R3は置換又は非置換の一価炭化水素基であり、Z1は炭素原子数5個以上の非置換又は置換の二価炭化水素基であり、Z2は非置換又は置換の二価炭化水素基である。)
(R’O)3-c R3 c Si-C8H16-NH-C2H4-NH2 (4)
(式(4)中、cは、0~2の整数であり、R’Oは加水分解性基であり、R3は置換又は非置換の一価炭化水素基である。)
〈1〉~〈4〉のいずれか1記載の室温硬化性オルガノポリシロキサン組成物の硬化物を有する自動車用部品又は自動車用オイルシール。
〈1〉~〈4〉のいずれか1記載の室温硬化性オルガノポリシロキサン組成物の硬化物を有する電気用部品又は電子用部品。
〈1〉~〈4〉のいずれか1記載の室温硬化性オルガノポリシロキサン組成物の硬化物を有する建築用構造物又は土木工事用構造物。
〈1〉~〈4〉のいずれか1記載の室温硬化性オルガノポリシロキサン組成物を含む接着剤、シーリング材、ポッティング剤又はコーティング剤。
(A)成分は、ケイ素原子に結合した水酸基(即ち、シラノール基)及び/又は加水分解性基を分子鎖両末端に有するジオルガノポリシロキサンであり、本発明のオルガノポリシロキサン組成物の主剤(ベースポリマー)である。該ジオルガノポリシロキサンの分子構造は特に制限されるものでなく、直鎖状、分岐鎖状、分岐構造を有する直鎖状のいずれであってもよいが、好ましくは、主鎖が基本的にジオルガノシロキサン単位の繰返しからなり、分子鎖両末端がケイ素原子に結合した水酸基(シラノール基)及び/又は加水分解性シリル基(例えば、ジオルガノヒドロキシシリル基及び/又は1~3個の加水分解性基を含有するトリオルガノシリル基(ジオルガノアルコキシシリル基、オルガノジアルコキシシリル基、トリアルコキシシリル基など))で封鎖された直鎖状のジオルガノポリシロキサンである。該直鎖状ジオルガノポリシロキサンは、分岐構造を少量有していてもよい。また、該ジオルガノポリシロキサンは分子鎖中(特には、分子鎖両末端のシラノール基及び/又は加水分解性シリル基と主鎖を構成するジオルガノシロキサン単位の繰返し構造との連結部等)にシルアルキレン構造(-SiRSi-)などを有するものであってもよい。前記式においてRは、炭素原子数1~20、好ましくは2~6の二価炭化水素基(例えば、直鎖状又は分岐状のアルキレン基等)である。また、炭素原子に結合する水素原子の一部又は全部がハロゲン原子、又はシアノ基で置換されているものであってもよい。
なお、粘度は回転粘度計(例えば、BL型、BH型、BS型、コーンプレート型、レオメーター等)などによって測定したものである。
アルコキシ置換アルコキシ基としては、全炭素原子数2~10、特に全炭素原子数3又は4のアルコキシ置換アルコキシ基が好ましく、例えば、メトキシメトキシ基、メトキシエトキシ基、エトキシメトキシ基が挙げられる。
特に、ジオルガノポリシロキサンの両末端に水酸基(シラノール基)、メトキシ基又はエトキシ基を有するのが好ましい。
(A)成分は、本発明の室温硬化性オルガノポリシロキサン組成物中、99~20質量%含有することが好ましく、特に95~50質量%含有することが好ましい。
(B)成分は、ケイ素原子に結合した加水分解性基を分子中に3個以上有する、加水分解性オルガノシラン化合物及び/又はその部分加水分解縮合物(即ち、残存加水分解性基を3個以上有するシロキサンオリゴマー等のシロキサン化合物)である。(B)成分は分子中に3個以上存在する加水分解性基が上記(A)成分中の末端シラノール基及び/又は加水分解性シリル基と加水分解・縮合反応して架橋構造を形成する架橋剤(硬化剤)として作用するものである。但し、本発明において、該(B)成分は上記(A)成分及び後述する(C)成分とは異なる化合物とする。特に、(B)成分は、分子中に2官能性のジオルガノシロキサン単位からなる繰返し構造を本質的に含有しないものである点において(A)成分と差別化されるものであり、また、(B)成分は、炭素原子数5個以上の二価炭化水素基を介してケイ素原子に結合した窒素原子を分子中に含有しないものである点において、後述する(C)成分とは明確に差別化されるものである。
(C)成分は、(A)成分及び(B)成分以外の、分子中に加水分解性基及び2個の窒素原子を有し、かつ、その内1個の窒素原子が炭素原子数5個以上の二価炭化水素基を介してケイ素原子に結合したものである、加水分解性シラン化合物及び/又はその部分加水分解縮合物(シロキサンオリゴマー等のシロキサン化合物)である。
なお、(C)成分中に2個存在する窒素原子は、通常、ケイ素原子に結合した同一の1価有機基(置換一価炭化水素基)の途中又は末端に存在するものであって、その内、ケイ素原子により近い方の窒素原子が炭素原子数5個以上の二価炭化水素基を介してケイ素原子に結合しているものである。
(C)成分は、本発明の室温硬化性オルガノポリシロキサン組成物の硬化物(シリコーンゴム)が各種の基材(特に、難接着性の基材)に対する優れた(初期)接着性及び浸水接着性を発現する上で重要な構成要素である。本発明の室温硬化性オルガノポリシロキサン組成物が、硬化して汎用樹脂(アクリル(AC)樹脂、ポリブチレンテレフタレート(PBT)樹脂、ポリカーボネート(PC)樹脂、アクリロニトリル-ブタジエン-スチレン(ABS)樹脂)及び金属(アルミニウム、銅、ステンレス)に対して良好に接着し、かつ浸水接着性が良好であることに、(C)成分は大きく貢献していると推察される。その理由は、分子中の2個の窒素原子の内1個窒素原子が炭素原子数5個以上の二価炭化水素基を介してケイ素原子に結合したものであるため、分子中の窒素原子と加水分解性シリル基中のケイ素原子との間に長鎖アルキルスペーサーを有するため、上記汎用樹脂や金属と強く結合するためと推察される。そのため、(C)成分は、接着向上剤(接着促進剤)として、本発明の重要な構成要素である。
(R’O)3-c R3 c Si-Z1 -NH-Z2 -NH2 (3)
(R’O)3-c R3 c Si-C8H16-NH-C2H4-NH2 (4)
N-2-(アミノエチル)-5-アミノペンチルトリメトキシシラン、
N-2-(アミノエチル)-6-アミノヘキシルトリメトキシシラン、
N-2-(アミノエチル)-7-アミノヘプチルトリメトキシシラン、
N-2-(アミノエチル)-8-アミノオクチルトリメトキシシラン、
N-2-(アミノエチル)-9-アミノノニルトリメトキシシラン、
N-2-(アミノエチル)-10-アミノデシルトリメトキシシラン、
N-2-(アミノエチル)-11-アミノウンデシルトリメトキシシラン、
N-2-(アミノエチル)-12-アミノドデシルトリメトキシシラン、
N-2-(アミノエチル)-13-アミノトリデシルトリメトキシシラン、
N-2-(アミノプロピル)-8-アミノオクチルトリメトキシシラン、
N-2-(アミノブチル)-8-アミノオクチルトリメトキシシラン、及び、
これらの各例示シラン化合物においてメトキシ基が全てエトキシ基で置換されたものなどが挙げられる。
また、本発明の効果を阻害しない限りにおいて、上記(A)~(D)成分以外に、樹脂組成物(特には、シリコーンゴム組成物)用に一般に知られている添加剤を任意成分としてさらに含有することができる。該添加剤としては、乾式法シリカ(煙霧質シリカ又はヒュームドシリカ)、湿式法シリカ(沈降シリカ)、ゾル-ゲル法シリカ、コロイダルシリカ、溶融シリカ(球状シリカ)、結晶性シリカ(石英微粉末)等のシリカ系充填剤、コロイダル炭酸カルシウム、重質(又は粉砕法)炭酸カルシウム、石英微粉末、ケイソウ土粉末、水酸化アルミニウム粉末、微粒子状アルミナ、マグネシア粉末、酸化亜鉛粉末、及びこれらをシラン類、シラザン類、低重合度ポリシロキサン類等で表面処理した微粉末状の無機質充填剤;顔料、染料、蛍光増白剤等の着色剤;抗菌剤、防カビ剤、可塑剤等が挙げられる。
(A-1)分子鎖両末端にケイ素原子に結合した水酸基(シラノール基)をそれぞれ一つずつ有する、分子鎖両末端ヒドロキシジメチルシロキシ基封鎖ポリジメチルシロキサン(信越化学工業株式会社製、粘度50,000mPa・s)
(B-1)メチルトリメトキシシラン
(B-2)メチルトリス(メチルエチルケトオキシム)シラン
(B-3)ビニルトリイソプロペノキシシラン
(C-1)N-2-(アミノエチル)-5-アミノペンチルトリメトキシシラン
(C-2)N-2-(アミノエチル)-8-アミノオクチルトリメトキシシラン(信越化学工業株式会社製)
(C-3)N-2-(アミノエチル)-11-アミノウンデシルトリメトキシシラン
(C-4)N-2-(アミノエチル)-3-アミノプロピルトリメトキシシラン(信越化学工業株式会社製)
(C-5)3-アミノプロピルトリエトキシシラン(信越化学工業株式会社製)
(D-1)ジオクチルスズジラウレート
(E-1)煙霧質シリカ(商品名;MU-215、ジメチルジクロロシラン表面疎水化処理品、BET比表面積;120m2/g、水分量0.5質量%、信越化学工業株式会社製)
分子鎖両末端にケイ素原子に結合した水酸基(シラノール基)をそれぞれ一つずつ有する分子鎖両末端ヒドロキシジメチルシロキシ基封鎖ポリジメチルシロキサン(A-1)100部と、煙霧質シリカ(E)10部とを、均一に混合し、(B-1)5部、(C-1)1部、(D-1)0.1部を順次加えて均一に混合して、室温硬化性オルガノポリシロキサン組成物を調製した。尚、混合は、万能混合機を用いて行った。
表1に示す組成で実施例1と同様にして室温硬化性オルガノポリシロキサン組成物を調製した。
表2に示す組成で実施例1と同様にして室温硬化性オルガノポリシロキサン組成物を調製した。
上記で得られた各組成物について、下記に示す方法により接着性を評価した。
被着体上に厚さ約2mmとなるように、上記各組成物を塗布し、室温にて7日間静置した。その後、手で引っ張る簡易接着性試験を実施した。
また室温にて7日間静置後に、40℃の水に7日間浸漬した場合についても、同様の簡易接着性試験を実施した。
引っ張り後の破壊状態が凝集破壊である場合を良好(○)と評価し、接着破壊(接着面での界面剥離)である場合を不良(×)と評価した。
被着体には、アクリル(AC)樹脂、ポリブチレンテレフタレート(PBT)樹脂、ポリカーボネート(PC)樹脂、アクリロニトリル-ブタジエン-スチレン(ABS)樹脂、アルミニウム(Al)、銅(Cu)及びステンレス(SUS)を用いて評価を行った。
結果を表1,2に示す。なお、B-2硬化剤は銅に対する腐食性があるため、銅に対する接着性試験は行っていない。
一方、表2に示す通り、本発明の(C)成分の代わりに、(C-4)、(C-5)といった、分子中に2個の窒素原子を有するものであっても窒素原子が炭素原子数3個の二価炭化水素基を介してケイ素原子に結合したシラン化合物、あるいは、分子中に窒素原子を1個しか有さないシラン化合物のような、従来の接着向上剤を配合した場合には、各種被着体に対する接着性が悪く、浸水試験後は多くの被着体に対して剥離してしまう結果であった[比較例1~9]。
従って、本発明品は、汎用樹脂(アクリル(AC)樹脂、ポリブチレンテレフタレート(PBT)樹脂、ポリカーボネート(PC)樹脂、アクリロニトリル-ブタジエン-スチレン(ABS)樹脂)及び金属(アルミニウム、銅、ステンレス)への接着性に優れ、かつ浸水接着性に優れたシリコーンゴム硬化物を与える室温硬化性オルガノポリシロキサン組成物であることがわかる。
Claims (8)
- (A)ケイ素原子に結合した水酸基及び/又は加水分解性基を分子鎖両末端に有し、25℃における粘度が20~1,000,000mPa・sであるジオルガノポリシロキサン:100質量部、
(B)(A)成分以外の、ケイ素原子に結合した加水分解性基を分子中に3個以上有する加水分解性シラン化合物及び/又はその部分加水分解縮合物:(A)成分100質量部に対して0.1~40質量部、並びに
(C)(A)成分及び(B)成分以外の、分子中に加水分解性基及び2個の窒素原子を有し、かつ、その内1個の窒素原子が炭素原子数5個以上の二価炭化水素基を介してケイ素原子に結合したものである、加水分解性シラン化合物及び/又はその部分加水分解縮合物:(A)成分100質量部に対して0.001~10質量部
を含有する室温硬化性オルガノポリシロキサン組成物。 - (C)成分が、下記一般式(3)で示されるシラン化合物及び/又はその部分加水分解縮合物である請求項1記載の室温硬化性オルガノポリシロキサン組成物。
(R’O)3-c R3 c Si-Z1 -NH-Z2 -NH2 (3)
(式(3)中、cは、0~2の整数であり、R’Oは加水分解性基であり、R3は置換又は非置換の一価炭化水素基であり、Z1は炭素原子数5個以上の非置換又は置換の二価炭化水素基であり、Z2は非置換又は置換の二価炭化水素基である。) - (C)成分の一般式(3)において、Z1がCdH2d(dは5~13の整数を示す)で表される二価炭化水素基である請求項2記載の室温硬化性オルガノポリシロキサン組成物。
- (C)成分が、下記一般式(4)で示されるシラン化合物及び/又はその部分加水分解縮合物である請求項1~3のいずれか1項記載の室温硬化性オルガノポリシロキサン組成物。
(R’O)3-c R3 c Si-C8H16-NH-C2H4-NH2 (4)
(式(4)中、cは、0~2の整数であり、R’Oは加水分解性基であり、R3は置換又は非置換の一価炭化水素基である。) -
請求項1~4のいずれか1項記載の室温硬化性オルガノポリシロキサン組成物の硬化物を有する自動車用部品又は自動車用オイルシール。 - 請求項1~4のいずれか1項記載の室温硬化性オルガノポリシロキサン組成物の硬化物を有する電気用部品又は電子用部品。
- 請求項1~4のいずれか1項記載の室温硬化性オルガノポリシロキサン組成物の硬化物を有する建築用構造物又は土木工事用構造物。
- 請求項1~4のいずれか1項記載の室温硬化性オルガノポリシロキサン組成物を含む接着剤、シーリング材、ポッティング剤又はコーティング剤。
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CN109642079A (zh) * | 2016-08-26 | 2019-04-16 | 信越化学工业株式会社 | 脱醇型室温固化性有机聚硅氧烷组合物和用该组合物的固化物密封的物品 |
JP2021178933A (ja) * | 2020-05-15 | 2021-11-18 | 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及び物品 |
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JP7173302B2 (ja) * | 2019-04-10 | 2022-11-16 | 信越化学工業株式会社 | オイルシール用室温硬化性オルガノポリシロキサン組成物及び自動車用部品 |
CN111040724B (zh) * | 2019-12-26 | 2022-03-08 | 杭州矽能新材料有限公司 | 交联聚乙烯和硅橡胶的胶黏剂及制备方法、使用方法 |
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EP3249015A4 (en) | 2018-07-04 |
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CN107109064A (zh) | 2017-08-29 |
JPWO2016117206A1 (ja) | 2017-10-12 |
EP3249015A1 (en) | 2017-11-29 |
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