WO2021246386A1 - 硬化性ポリオルガノシロキサン組成物及び電子部品 - Google Patents
硬化性ポリオルガノシロキサン組成物及び電子部品 Download PDFInfo
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- WO2021246386A1 WO2021246386A1 PCT/JP2021/020781 JP2021020781W WO2021246386A1 WO 2021246386 A1 WO2021246386 A1 WO 2021246386A1 JP 2021020781 W JP2021020781 W JP 2021020781W WO 2021246386 A1 WO2021246386 A1 WO 2021246386A1
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- curable
- polyorganosiloxane
- component
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- 239000000203 mixture Substances 0.000 title claims abstract description 146
- 125000000524 functional group Chemical group 0.000 claims abstract description 55
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- 238000004132 cross linking Methods 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
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- 238000000034 method Methods 0.000 claims description 22
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 238000009833 condensation Methods 0.000 claims description 11
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- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
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- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- OLTVTFUBQOLTND-UHFFFAOYSA-N tris(2-methoxyethoxy)-methylsilane Chemical compound COCCO[Si](C)(OCCOC)OCCOC OLTVTFUBQOLTND-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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Definitions
- the present invention relates to a curable polyorganosiloxane composition whose state of application to a substrate can be easily confirmed. It also relates to a method for confirming an application state of the composition to a substrate.
- compositions that cure at room temperature to produce a rubber-like elastic body have been conventionally known.
- This composition has applications such as coating materials and potting materials for electrical and electronic devices such as LCDs (Liquid Crystal Display).
- LCDs Liquid Crystal Display
- Such a composition has good workability, is less likely to corrode electrodes and wiring, and is also excellent in adhesiveness and the like.
- the adhesive using the polyorganosiloxane composition can be in the form of a two-component type in which the composition is divided into a main agent and a curing agent and mixed at the time of use from the viewpoint of operability and deep curability. ..
- the polyorganosiloxane composition In adhering a base material, it is necessary for the polyorganosiloxane composition as an adhesive to uniformly exert an adhesive force on the base material in order to ensure the strength and reliability of the adhesion.
- the main agent and the curing agent In the case of a two-component type consisting of a main agent and a curing agent, the main agent and the curing agent must be uniformly mixed before being applied to the substrate as a prerequisite for exhibiting uniform adhesive strength. Means for confirming the state have been studied (Japanese Patent Laid-Open No. 2019-143074).
- an adhesive may be colored by blending a pigment or the like, but on the other hand, there are various types of base materials including the color. Depending on the type of base material, the silicone adhesive and the base material may have similar colors. When the base material and the adhesive have similar colors, it may be difficult to confirm the applied state by discrimination using visible light. If it cannot be confirmed that the application is uniform, the adhesion to the substrate may be incomplete, which adversely affects the reliability of the product.
- the present invention provides a colored silicone adhesive, which makes it easy to confirm whether or not the adhesive is uniformly applied to a substrate of a similar color, and a method for confirming an applied state using the adhesive.
- the purpose is.
- a main aspect of the present invention is (a) a polyorganosiloxane having two or more curable functional groups in one molecule; (b) a crosslinked group having reactivity with the curable functional group of (a) above.
- a cross-linking agent having two or more of the above in one molecule (c) a curing catalyst capable of catalyzing the cross-linking reactions of (a) and (b) above; (d) a pigment that does not fluoresce itself; and (e).
- a curable polyorganosiloxane composition comprising a UV tracer.
- another aspect of the present invention is a step of providing the composition; a step of providing a base material having a color difference ( ⁇ E) of 20 or less from the composition; applying the composition to the base material.
- Step; A method for confirming the application state of the curable polyorganosiloxane composition to the substrate which comprises a step of irradiating the composition applied to the substrate with ultraviolet rays.
- the present invention provides an adhesive that makes it easy to confirm whether or not it has been uniformly applied to a substrate of a similar color. Further, there is provided a method of using a curable polyorganosiloxane composition as an adhesive and confirming an application state to a substrate having a similar color to the adhesive.
- organic group means a group containing carbon.
- the valence of an organic group is indicated by describing n as an arbitrary natural number as “n-valent”.
- n-valent organic group means a carbon-containing group having only one bond. The bond may be possessed by an element other than carbon. Even if the valence is not specified, a person skilled in the art can grasp a suitable valence from the context.
- the "hydrocarbon group” means a group containing carbon and hydrogen, from which one hydrogen atom has been desorbed from the molecule.
- the hydrocarbon group is not particularly limited, but may be substituted with one or more substituents, such as a hydrocarbon group having 1 to 20 carbon atoms, for example, an aliphatic hydrocarbon group. , Aromatic hydrocarbon groups and the like.
- the above-mentioned "aliphatic hydrocarbon group” may be linear, branched or cyclic, and may be saturated or unsaturated. Further, the hydrocarbon group may contain one or more ring structures.
- such a hydrocarbon group has one or more nitrogen atoms (N), oxygen atoms (O), sulfur atoms (S), silicon atoms (Si), amide bonds, and sulfonyls in its terminal or molecular chain. It may have a structure containing a hetero atom or a hetero atom such as a bond, a siloxane bond, a carbonyl group, or a carbonyloxy group.
- the substituent of the "hydrocarbon group” is not particularly limited, but may be, for example, a halogen atom; substituted with one or more halogen atoms, C 1-6 alkyl.
- a halogen atom substituted with one or more halogen atoms, C 1-6 alkyl.
- Examples include groups selected from groups, C 6-10 aryl groups and 5-10 membered heteroaryl groups.
- the alkyl group and the phenyl group may be unsubstituted or substituted unless otherwise specified.
- the substituent of such a group is not particularly limited, and for example, one or more groups selected from a halogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group and a C 2-6 alkynyl group may be used. Can be mentioned.
- the curable polyorganosiloxane composition of the present invention contains at least one polyorganosiloxane having two or more curable functional groups in the molecule as the component (a).
- the component (a) functions as a base polymer of the curable polyorganosiloxane composition.
- the "curable functional group” refers to a functional group capable of causing a curing reaction.
- the mechanism of the curing reaction is not particularly limited, and a method generally used for curing the resin can be adopted. As the curing reaction, a condensation reaction or an addition reaction is particularly adopted.
- each curable functional group contained in one molecule is the same functional group, but if it is a functional group that causes the same kind of curing reaction, even different kinds of functional groups are mixed in the same molecule. can do.
- the curable functional group is preferably present at least one at each end of the molecular main chain of the component (a). Further, here, in the present specification, the molecular main chain of the component (a) represents a relatively longest binding chain in the molecule of the component (a).
- the molecular skeleton of the component (a) is not particularly limited as long as the siloxane bond is the main skeleton.
- the siloxane skeleton may be interrupted by a divalent organic group.
- the structural unit of the siloxane compound may be described by the following abbreviations. Hereinafter, these structural units may be referred to as "M unit”, “D unit”, etc., respectively.
- the siloxane compound is constructed by combining the above structural units, but the methyl group of the structural unit is a halogen such as fluorine, a hydrocarbon group such as a phenyl group, etc. It may contain at least a partial replacement of the base of.
- the case of DH 20 D 20 is not intended to be followed by 20 DH units and then 20 D units, and each unit may be arbitrarily arranged.
- the siloxane compound can have various three-dimensional structures depending on the T unit or the Q unit. Therefore, the component (a) can take any molecular skeleton such as linear, branched chain, cyclic, and a combination of these structures.
- the component (a) preferably has a linear molecular skeleton.
- the component (a) is the following formula (1): (R a ) 3-p R p Si-O- (Si (R) r (R a ) 2-r O) n- SiR q (R a ) 3-q ... (1)
- Ra is a curable functional group independently of each other.
- R is a monovalent organic group independently of each other.
- p and q are 0, 1 or 2, respectively, independently of each other.
- r is 0, 1 or 2 independently of each other.
- n is a number having a viscosity at 23 ° C. of 0.01 to 50 Pa ⁇ s).
- the linear polyorganosiloxane represented by is exemplified.
- R those having a hydrocarbon group, particularly an alkyl group, an alkenyl group and an aryl group are preferable. From the viewpoint of controlling physical properties such as the refractive index, at least a part of R may be an aryl group such as a phenyl group or an alkenyl group such as a vinyl group. Polyorganosiloxanes in which R is all methyl are particularly preferably used because of their availability. Regarding the position of the curable functional group, the polyorganosiloxane having r of 2 in the above formula (1), that is, the linear polyorganosiloxane having at least one curable functional group only at both ends of the molecule. preferable.
- the component (a) has two or more functional groups in one molecule that can be used for the curing reaction of the siloxane resin.
- the component (a) is a polyorganosiloxane having two or more Si atoms bonded to at least one group selected from the group consisting of a hydroxyl group and a hydrolyzable group. Can be.
- hydrolyzable group means a group that is susceptible to a hydrolysis reaction, i.e., a group that can be desorbed from the main skeleton of a compound by a hydrolysis reaction.
- R'in examples include unsubstituted alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, n-butyl group and isobutyl group; substituted alkyl groups such as chloromethyl group.
- an alkyl group, particularly an unsubstituted alkyl group is preferable, and a methyl group or an ethyl group is more preferable.
- the hydroxyl group is not particularly limited, but may be generated by hydrolyzing a hydrolyzable group.
- the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom, and among these, a chlorine atom is preferable.
- polyorganosiloxane having a curable functional group that causes a condensation reaction p and q are 0 or 1 and r is 2 in the above formula (1), that is, 2 or 3 only at the molecular end. Each has a total of 4 or 6 hydrolyzable groups, particularly those having an alkoxy group.
- a linear polyorganosiloxane having both ends sealed with a methyldimethoxysilyl group or a trimethoxysilyl group can be mentioned. ..
- a commercially available product can be used.
- a polyorganosiloxane having a curable functional group introduced by a known reaction may be used.
- the component (a) contains two Si atoms bonded to an aliphatic unsaturated bond, particularly a group having an alkenyl group, such as a (meth) acrylic group or a vinyl group that is cured by an addition reaction. It can also be a compound having the above.
- the curable functional group that causes the addition reaction is more preferably a vinyl group.
- the aliphatic unsaturated groups, a curable functional group corresponding to the group R a in the formula (1) is more preferably a vinyl group.
- polyorganosiloxane having a curable functional group that causes an addition reaction p and q are 2 and r is 2 in the above formula (1), that is, one at each molecular terminal, for a total of two. Those having two addition-reactive groups, particularly vinyl groups, are preferable.
- a linear polyorganosiloxane having both ends sealed with a dimethylvinylsilyl group and the like can be mentioned.
- a polyorganosiloxane that can be used as such a component (a) a commercially available product can be used. Further, a polyorganosiloxane having a curable functional group introduced by a known reaction may be used.
- the blending amount of the component (a) is not particularly limited as long as it is within the range of the viscosity that the curable polyorganosiloxane composition can handle. Based on the amount of the component (a), the blending amount of the other components can be appropriately set within a preferable range shown individually below.
- the cross-linking agent in the curable composition of the present invention has two or more cross-linking groups in one molecule having reactivity with the curable functional group of the component (a) (hereinafter, simply "component (hereinafter,” component (). b) ”).
- component (a) hereinafter, simply "component (hereinafter,” component (). b)
- component (b) By including the cross-linking agent, the physical characteristics of the cured product obtained from the curable composition, for example, the tensile strength and the elastic modulus are improved.
- the cross-linking group of the component (b) a functional group that is generally active in the reaction used for the curing reaction of silicone can be used, and is determined according to the reactive functional group of the component (a).
- the reactive functional group of the component (a) is a functional group capable of conducting a condensation reaction such as a hydroxyl group or an alkoxy group
- hydrolysis such as a hydroxyl group or an alkoxy group directly bonded to silicon as a cross-linking group Sex groups
- the reactive functional group of the component (a) is a functional group capable of performing an addition reaction such as a vinyl group
- a hydrogen atom directly bonded to silicon, that is, a Si—H group may be adopted as the cross-linking group.
- the number of cross-linking groups that the component (b) has per molecule needs to be two or more in order to form a cross-linking structure between the components (a), but the cross-linking reaction brings about a network structure. It is preferably 3 or more.
- Each cross-linking group may be bonded to the same silicon atom or may be bonded to a different silicon atom.
- the component (b) may be a compound having only one silicon, that is, a derivative of silane, or a compound having two or more silicons.
- the component (b) preferably has a structure in which each silicon atom is linked by a siloxane bond in which each silicon atom is crosslinked with oxygen.
- the molecular skeleton of the component (b) containing two or more silicon atoms may be linear, branched or cyclic.
- the component (b) is a compound having at least two hydroxyl groups or hydrolyzable groups bonded to a Si atom (however, the component (a)). ) Or a partially hydrolyzed condensate thereof.
- Hydrolytic groups include alkoxy groups such as methoxy, ethoxy, propoxy and butoxy groups; substituted alkoxy groups such as 2-methoxyethoxy and 2-ethoxyethoxy groups; enoxy groups such as isopropenoxy groups.
- Examples thereof include a ketoximato group such as a methylethylketooxym group, an acetoxy group, and the like, and they may be the same or different from each other.
- Each hydrolyzable group may be bonded to the same silicon atom or may be bonded to a different silicon atom.
- a compound having a structure in which a hydroxyl group or a hydrolyzable group bonded to a Si atom is linked by a siloxane bond can also be used as a cross-linking agent.
- the groups bonded to the silicon atom other than the hydrolyzable group can be independently monovalent organic groups.
- a hydrocarbon group is preferable, and a methyl group, a vinyl group, and a phenyl group are particularly preferable, because the corresponding silicon compound can be easily obtained.
- R 1 is an independently substituted or unsubstituted monovalent hydrocarbon group
- R 2 is an independently hydrogen atom or a monovalent organic group
- a is. 0, 1 or 2
- examples thereof include an organosilicon compound represented by (1) or a partially hydrolyzed condensate thereof.
- R 2 is an independent hydrogen atom or a monovalent organic group.
- a monovalent organic group means a group containing a monovalent carbon.
- the monovalent organic group is not particularly limited, and examples thereof include a monovalent hydrocarbon group. Hydrocarbon groups have the same meaning as above.
- R 1 is an independently substituted or unsubstituted monovalent hydrocarbon group having 1 to 12 carbon atoms.
- R 1 has a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a heptyl group, an octyl group and a nonyl group.
- Alkyl group such as decyl group; Cycloalkyl group such as cyclopentyl group, cyclohexyl group, cycloheptyl group; aryl group such as phenyl group, trill group, xylyl group, naphthyl group; benzyl group, phenylethyl group, phenylpropyl group and the like Aralkyl group; alkenyl group such as vinyl group, allyl group, propenyl group, butenyl group; alkynyl group such as ethynyl group, propynyl group; Groups substituted with halogen atoms (eg, chloromethyl group, bromoethyl group, chloropropyl group, trifluoropropyl group, 3,3,4,4,5,5,6,6,6-nonafluorohexyl group) and the like are used. Can be mentioned. And the ease of availability and the excellent cross-linking reaction rate is obtained, as
- R 2 is an independent hydrogen atom or a monovalent organic group.
- the monovalent organic group is not particularly limited, and examples thereof include a monovalent hydrocarbon group. Hydrocarbon groups have the same meaning as above.
- A is preferably 1 or 2.
- the cross-linking group of the component (b) may be bonded to the same silicon atom as in the above formula, but may be bonded to a different silicon atom.
- a compound having a structure in which two OR 2 groups bonded to silicon are linked by a divalent organic group can also be used as the component (b).
- the divalent organic group may be a divalent group composed of a siloxane bond or a divalent hydrocarbon group.
- the divalent hydrocarbon group examples include an alkylene group such as a methylene group, an ethylene group, a propylene group, a methylethylene group, a butylene group and a hexamethylene group; a cycloalkylene group such as a cyclohexylene group and a phenylene group. Allylene groups such as a trilen group, a xylylene group, a naphthylene group and a biphenylene group; a group in which some or all of the hydrogen atoms of these groups are substituted with a halogen atom or the like; and these substituted or unsubstituted alkylene groups and arylene groups. The combination is exemplified.
- a methylene group, an ethylene group, a propylene group, a butylene group, a hexamethylene group, a cyclohexylene group and a phenylene group are preferable, and an ethylene group, a propylene group, a butylene group and a phenylene group are particularly preferable.
- component (b) it can also be a cyclic siloxane having the group R 2 2 or more.
- the group R 2 may or may not be directly bonded to the silicon atom forming the siloxane ring.
- the cyclic siloxane preferably has a ring member number of 6 to 10, and more preferably 8. That is, it is preferable to form a ring containing 3 to 5, particularly 4 units of Si—O.
- the component (b) is tetramethoxysilane, methyltrimethoxysilane, vinyltrimethoxysilane, phenyltrimethoxysilane, tetraethoxysilane, methyltriethoxysilane, vinyltriethoxysilane, phenyltriethoxysilane, tetrapropoxy.
- Alkoxy group-containing compounds such as silane, tetraisopropoxysilane, dimethyldimethoxysilane, vinylmethyldimethoxysilane, dimethyldiethoxysilane and 3-chloropropyltrimethoxysilane and their partial hydrolysis condensates; tetrakis (2-ethoxyethoxy).
- Substituent alkoxy group-containing compounds such as silane, methyltris (2-methoxyethoxy) silane, vinyl (2-ethoxyethoxy) silane and phenyltris (2-methoxyethoxy) silane and their partial hydrolysis condensates; methyltripropeno Enoxy such as xysilane, methyltriisopropenoxysilane, vinyltriisopropenoxysilane, phenyltriisopropenoxysilane, dimethyldiisopropenoxysilane and methylvinyldiisopropenoxysilane and their partial hydrolysis condensates.
- Group-containing compounds examples thereof include acyloxy group-containing compounds such as methyltriacetoxysilane and their partial hydrolysis condensates.
- the component (b) preferably does not have other reactive functional groups in terms of crosslinkability, but may have a reactive functional group other than the crosslinkable group.
- a cross-linking agent not only contributes to a cross-linking reaction (condensation reaction), but can also function as an adhesion-imparting agent.
- examples of other reactive functional groups include a primary amino group, an epoxy group, a (meth) acryloyl group, a (meth) acryloyl group, a mercapto group, an isocyanato group and the like.
- cross-linking agent having a reactive functional group other than the cross-linking group with the component (a) examples include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, and 3-aminopropyltriisopropoxy.
- Silane 3-aminopropyltriacetamide silane, N- (2-aminoethyl) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyltriethoxysilane, N-methyl-3- Substituted or unsubstituted amino group-containing silanes such as aminopropyltrimethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, N, N-dimethyl-3-aminopropyltrimethoxysilane; 3-glycidoxypropyl Epoxy group-containing silanes such as trimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3,4-epoxycyclohexylethyltrimethoxysilane; 3-isosognitopropyltrimethoxysilane
- Isocyanurate compounds such as tris (3-trialkoxysilylpropyl) isocyanurate; silane compounds with a carbacilatran skeleton in which the oxygen of silatlan is replaced by one carbon; 3-acryloxypropyltrimethoxysilane, 3 -(Meta) acryloxy group-containing silanes such as methacryloxypropyltrimethoxysilane, 3-acryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane; 3-mercaptopropyl Examples thereof include mercapto group-containing silanes such as trimethoxysilane; and mixtures or reactants of primary amino group-containing silanes and epyl group-containing silanes.
- the cross-linking group of the component (b) includes a Si—H bond.
- the cross-linking agent having such a cross-linking group hydrogenpolyorganosiloxane, which is a siloxane containing a hydrogen group, is used.
- Hydrogen polyorganosiloxane is a siloxane compound having a Si—H bond and is a component serving as a cross-linking agent.
- Hydrogenpolyorganosiloxane is typically described by the following formula (3): (R b ) x (R c ) y SiO (4-xy) / 2 (3)
- R b is a hydrogen atom and R c is a C 1-6 alkyl group (eg, methyl, ethyl, propyl, butyl, pentyl, hexyl, preferably methyl) or a phenyl group;
- x is 1 or 2;
- y is an integer of 0 to 2, where x + y is 1 to 3). It has two or more units in the molecule indicated by.
- Examples of the siloxane skeleton in the hydrogen polyorganosiloxane include cyclic, branched and linear skeletons, preferably cyclic or linear skeletons, and more preferably linear skeletons.
- the main chain of the hydrogen polyorganosiloxane is preferably a linear skeleton, but may have a skeleton having a branched structure as a substituent.
- the number of hydrogen groups bonded to silicon atoms contained in one molecule must be at least 3 or more, but an average of 5 hydrogen groups per molecule. The above is preferable, and the number is more preferably eight or more.
- organic groups other than hydrogen groups, bond positions, degree of polymerization, structure, etc. are not particularly limited, but in the case of a linear structure, the degree of polymerization is 10 to 100, particularly 15 The range of about 70 is preferable because the handleability of the obtained composition tends to be further improved.
- Specific examples of the hydrogen polyorganosiloxane that can be used include a linear chain containing 8 or more units having a Si—H bond (MH or DH unit) and having a degree of polymerization in the range of 15 to 70. It is a hydrogen polyorganosiloxane having a skeleton.
- the blending amount of the hydrogen polyorganosiloxane is 0.7 to 5. that the hydrogen atom directly bonded to the silicon atom is 0.7 to 5. the curable functional group of the component (a), particularly one unsaturated group such as a vinyl group. The amount is preferably 0. If the number is less than 0.7, the curing may not proceed at a sufficient rate, and if the number exceeds 5.0, the cured product may become too hard and may adversely affect the physical properties after curing.
- the curable functional group is a vinyl group
- the amount of the polyorganosiloxane having one vinyl group in the molecule is the Si—H bond and the unsaturated bond of the hydrogen polyorganosiloxane, particularly the amount of the vinyl group.
- the H / Vi ratio is preferably in the range of 0.7 to 2.0, more preferably in the range of 0.8 to 1.5.
- the H / Vi ratio is preferably in the range of 0.7 to 2.0, more preferably in the range of 0.8 to 1.5.
- the molecular weight of the cross-linking agent (b) is 1,000 or less, preferably 600 or less, and more preferably 250 or less.
- the lower limit of the molecular weight of the cross-linking agent may be 90 or more, or may be 120 or more.
- component (b) only one may be used as long as it has a cross-linking group corresponding to the reactive functional group of the component (a), or any one capable of causing the same kind of reaction may be used. For example, two or more kinds may be used at the same time.
- the cross-linking agent (b) may contain, for example, 0.1 part by mass or more, specifically 0.3 parts by mass or more, and 30 parts by mass with respect to 100 parts by mass of the component (a) in the curable composition. It may contain 20 parts by mass or less, more specifically 10 parts by mass or less.
- the total content of the component (b) with respect to the component (a) is preferably 0.1% by mass or more, more preferably 0.3% by mass or more, and 30% by mass, from the viewpoint of crosslinkability. It is preferably less than or equal to, more preferably 20% by mass or less, and particularly preferably 10% by mass or less.
- the component (b) may contain, for example, 1 mol or more of a cross-linking group, specifically 2 mol or more, with respect to 1 mol of the reactive functional group of the component (a) in the curable composition. Can be done.
- the component (b) can contain, for example, 30 mol or less of a cross-linking group, specifically 20 mol or less, and more specifically, with respect to 1 mol of the reactive functional group of the component (a).
- the component (b) can contain a cross-linking group in the range of, for example, 1 to 30 mol, specifically in the range of 2 to 20 mol, with respect to 1 mol of the reactive functional group of the component (a). be able to.
- the curing catalyst in the curable composition of the present invention is a compound capable of catalyzing a cross-linking reaction between the component (a) and the component (b) (hereinafter, may be simply referred to as “component (c)”).
- component (c) a cross-linking reaction between the component (a) and the component (b)
- component (c) is an addition reaction.
- addition curing catalysts can be used respectively.
- the condensation catalyst as the component (c) is a component that promotes hydrolysis condensation between the above component (a) and the component (b).
- a metal-based catalyst an organic acid-based catalyst, an inorganic acid-based catalyst, a basic-based catalyst, or the like can be used. From the viewpoint of the curing rate of the composition, the condensation catalyst is preferably a metal-based catalyst.
- the metal atom contained in the metal catalyst examples include titanium, zirconium, tin and the like. In particular, it is preferably an organotin compound or an alkoxytitanium.
- a compound having an alkoxide as a ligand preferably an alkoxide having 1 to 4 carbon atoms, and more preferably an alkoxide having 1 to 3 carbon atoms can be used. When such a catalyst is used, it is easily dissolved or dispersed in the curable composition and can contribute to the promotion of a uniform condensation reaction.
- Preferred metal-based catalysts include carboxylic acid metal salts such as iron octoate, manganese octoate, zinc octoate, tinnaphthate, tincaprilate, tin olate; dibutyltin diacetate, dibutyltin dioctate, dibutyltin dilaurate, dibutyltin diorate, diphenyltindi.
- carboxylic acid metal salts such as iron octoate, manganese octoate, zinc octoate, tinnaphthate, tincaprilate, tin olate
- Organic tin compounds such as acetate, dibutyltin oxide, dibutyltin dimethoxydo, dibutylbis (triethoxysiloxy) tin, dioctylszirconiumate, dimethylstin dineodecanoate; tetraethoxytitanium, tetrapropoxytitanium, tetraisopropoxytitanium, tetran -Organic titaniums such as butoxytitanium, tetraisobutoxytitanium, diisopropoxytitanium bis (ethylacetoacetate), 1,3-propanedioxytitanium bis (ethylacetacetate); aluminum trisacetylacetonate, aluminumtrisethylacetate , Diisopropoxyaluminum ethylacetate, organic aluminum such as triethoxyaluminum; zirconium tetraacetylacetonate, t
- Examples of the organic acid-based catalyst include compounds having a carboxylic acid, a sulfonic acid, and a phosphoric acid, and specific examples thereof include acetic acid, trifluoroacetic acid, methanesulfonic acid, toluenesulfonic acid, and alkylphosphate. And so on.
- Examples of the inorganic acid-based catalyst include hydrochloric acid, sulfuric acid and the like.
- Examples of the basic catalyst include amine compounds such as ammonia, triethylamine and diethylamine, dialkylhydroxylamine such as dimethylhydroxyamine and diethylhydroxylamine, tetramethylguanidine, guanidyl group-containing silanes and guanidyl compounds such as siloxane.
- amine compounds such as ammonia, triethylamine and diethylamine, dialkylhydroxylamine such as dimethylhydroxyamine and diethylhydroxylamine, tetramethylguanidine, guanidyl group-containing silanes and guanidyl compounds such as siloxane.
- the condensation catalyst is preferably contained in the curable composition of the present invention in an amount of 0.01 to 10.0 parts by mass, preferably 0.03 to 5.0 parts by mass, based on 100 parts by mass of the component (a). Is more preferable.
- condensation catalyst only one kind may be used, or two or more kinds may be used at the same time.
- an addition curing type catalyst is used as the curing catalyst.
- a typical example is a platinum catalyst.
- the platinum catalyst is a curing catalyst for reacting the curable functional group of the component (b) with the hydrogen group of the component (b) to obtain a cured product.
- the platinum compound include platinum chloride acid, platinum olefin complex, platinum vinyl siloxane complex, platinum phosphorus complex, platinum alcohol complex, platinum black and the like.
- the blending amount is an amount of 0.1 to 1000 ppm as a platinum element with respect to the component (a).
- reaction inhibitors for platinum group metals include acetylene alcohols such as 2-methyl-3-butyne-2-ol and 1-ethynyl-2-cyclohexanol, and diallyl maleate.
- the curable composition of the present invention contains a pigment as a colorant (hereinafter, may be simply referred to as "component (d)").
- a pigment a known colored inorganic or organic substance that does not have reactivity with other components contained in the curable composition of the present invention and is generally treated as a pigment may be used. can.
- colored means that at least a part of visible light is absorbed or scattered, that is, it is not transparent.
- the pigment may be of natural origin or may be artificially synthesized or prepared. However, the pigment itself does not emit fluorescence.
- pigments include carbon black (black), titanium oxide, zinc flower, white lead, barium sulfate (white), lead tan, iron oxide (red), chrome yellow, zinc yellow (yellow), and pursian blue. (Blue) and the like.
- One of these pigments may be used alone, or two or more of these pigments may be mixed and used.
- the type of pigment is also related to the substrate to which the composition is applied, but is preferably selected from the group consisting of carbon black, titanium oxide, iron oxide and mixtures thereof.
- the content of the pigment is not particularly limited as long as it can be uniformly mixed in the composition, and the color of the composition, particularly the brightness, can be adjusted by the concentration of the pigment.
- the curable composition of the present invention preferably contains 0.01 to 10 parts by mass, more preferably 0.1 to 5 parts by mass, based on 100 parts by mass of the component (a).
- the curable composition of the present invention includes a UV tracer (hereinafter, may be simply referred to as "component (e)").
- a UV tracer is a compound that absorbs ultraviolet rays and emits fluorescence.
- a colorless compound that absorbs light having a wavelength shorter than 440 nm and emits fluorescence, particularly blue to purple fluorescence is preferable.
- the UV tracer include benzoxazole derivatives such as 2,5-thiophendiylvir (5-tert-butyl-1,3-benzoxazole), stylben derivatives, imidazole derivatives, coumarin derivatives, and fluorescein derivatives such as rhodamine. Commonly known compounds such as can be used. Specific examples of commercially available products include Tinopal OB manufactured by BASF.
- the amount of the component (e) added is preferably 0.001 to 1 part by mass, preferably 0.005 to 0.1 part by mass, based on 100 parts by mass of the component (a) in the curable composition of the present invention. It is more preferable that the portion is contained. If the amount added is less than 0.001 part by mass with respect to 100 parts by mass of the component (a), the fluorescence when irradiated with ultraviolet rays may not be sufficient and it may be difficult to confirm the applied state.
- the curable polyorganosiloxane of the present invention contains the above components (a) to (e). In particular, it can be classified into a moisture curing type and an addition curing type according to the classification according to the curing method.
- the type of polyorganosiloxane composition that is cured by moisture is a hydroxyl group in which a polyorganosiloxane having a curable functional group that causes a condensation reaction as the component (a) is bonded to a Si atom as the component (b).
- the composition comprises a compound having at least two hydrolyzable groups and a condensation catalyst as the component (c).
- the (a) is a polyorganosiloxane having two or more hydroxyl groups and / or alkoxy groups in the molecule, wherein (b) is of the formula R 1 a Si (OR 2) 4-a (wherein R 1 is an independently monovalent organic group, R 2 is an independent hydrogen atom or a monovalent organic group, and a is 0, 1 or 2).
- R 1 is an independently monovalent organic group
- R 2 is an independent hydrogen atom or a monovalent organic group
- a is 0, 1 or 2
- the type of polyorganosiloxane composition that is cured by an addition reaction to an unsaturated bond is a polyorganosiloxane having a curable functional group that causes an addition reaction as the above component (a), and the polyorganohydrogen as the above component (b). It is a composition having siloxane as the above-mentioned component (c) and a platinum catalyst, respectively.
- the above (a) is a polyorganosiloxane having two or more alkenyl groups in one molecule
- the above (b) is a hydro having a hydrogen atom bonded to three or more silicon atoms in one molecule.
- examples thereof include a curable polyorganosiloxane composition which is a gempolyorganosiloxane, wherein (c) is a platinum compound.
- the polyorganosiloxane composition of the present invention is not particularly limited in its properties as long as each component is uniformly mixed and has a fluidity to the extent that it can be applied to a substrate.
- the viscosity of the polyorganosiloxane composition can be controlled mainly by the viscosity of the component (a), and is preferably in the range of 0.1 to 100 Pa ⁇ s from the viewpoint of operability.
- the polyorganosiloxane composition is preferably a one-component composition in which all the components are mixed. In the one-component composition, in order to prevent curing in the storage state, it can be stored in a dry state or a reaction inhibitor can be added, and the method thereof is known to those skilled in the art.
- the curable polyorganosiloxane composition of the present invention may contain other known components as long as it does not impair its purpose and curing.
- a flame retardant, a filler, an adhesive-imparting agent, a heat-resistant imparting agent, a diluent, an organic solvent and the like can be appropriately blended.
- a siloxane resin that does not correspond to the component (a) can also be blended. Examples of such a resin include polyorganosiloxane having only one curable functional group, polyorganosiloxane having no curable functional group such as dimethylsiloxane, and the like. Of these resins, non-reactive resins can be used as diluents.
- the curable polyorganosiloxane composition may further comprise a filler.
- a filler oxides such as fumigant silica, calcined silica, silica aerogel, precipitated silica, silicate soil, crushed silica, molten silica, quartz powder, fumigant titanium oxide, iron oxide, zinc oxide, titanium oxide, and aluminum oxide; These surfaces are treated with a hydrophobic agent such as trimethylchlorosilane, dimethyldichlorosilane, hexamethyldisilazane and octamethylcyclotetrasiloxane; carbonates such as calcium carbonate, magnesium carbonate and zinc carbonate; aluminosilicic acid and calcium silicate.
- Silicates such as; talc; composite oxides such as glass wool, mica fine powder; conductive fillers such as carbon black, copper powder, nickel powder; polymethylsilsesquioxane, polystyrene, polyvinyl chloride, polypropylene, etc. Synthetic resin powder; fibrous fillers such as asbestos, glass fiber, and organic fiber are exemplified. These fillers are selected according to the coating workability and the physical characteristics required for the rubber-like elastic body obtained by curing.
- the average particle size thereof is preferably 100 ⁇ m or less, more preferably 100 ⁇ m or less, from the viewpoint of dispersibility, fluidity of the curable composition, and high mechanical strength of the cured product. Is 50 ⁇ m, particularly preferably 10 ⁇ m or less.
- the measured value of the average particle size is the median diameter (d50) measured by the laser diffraction / scattering method.
- the filler can be contained in, for example, 200 parts by mass or less, specifically 1 to 100 parts by mass, based on 100 parts by mass of the component (a) in the curable polyorganosiloxane composition. More specifically, it can contain 1 to 50 parts by mass.
- the curable polyorganosiloxane composition may further contain an adhesive-imparting agent.
- the adhesion-imparting agent is a component that improves the adhesion of the cured product of the composition to a substrate such as glass, metal, or plastic.
- a compound having a functional group other than the hydrolyzable group in the above-mentioned cross-linking agent can also be used as the adhesion-imparting agent. Specific examples thereof include amino group-containing silanes, isocyanates, and carbacilatran compounds.
- the adhesive-imparting agent may be contained in the curable polyorganosiloxane composition in an amount of, for example, 10 parts by mass or less, specifically 0.01 to 10 parts by mass, with respect to 100 parts by mass of the component (a). More specifically, it can contain 0.1 to 5 parts by mass.
- the curable polyorganosiloxane composition may further contain a siloxane resin that does not correspond to the components (a) and (b). Such resins can also be used as diluents for adjusting the viscosity.
- a siloxane resin the following formula (4): (R a ) 3-p R p Si-O- (SiR 2 O) n- SiR 3 ... (4) (In the equation, Ra , R, p, n are as defined in the equation (1)).
- a siloxane having no curable functional group, as shown by, can be used.
- a siloxane resin By using such a siloxane resin, it is possible to control the hardness of the curable polyorganosiloxane composition when it is cured and the viscosity of the composition, and it is possible to control the handleability and the required physical properties. Can be widely handled.
- Such a resin can be contained in, for example, 50 parts by mass or less, specifically 0.1 to 50 parts by mass, with respect to 100 parts by mass of the component (a) in the curable polyorganosiloxane composition. More specifically, it can contain 1 to 30 parts by mass.
- the curable polyorganosiloxane composition may contain a solvent.
- the curable polyorganosiloxane composition can be used by dissolving it in a suitable solvent at a desired concentration depending on its use and purpose.
- the concentration of the solvent may be, for example, 80 parts by mass or less, 50 parts by mass or less, or 30 parts by mass or less with respect to 100 parts by mass of the curable polyorganosiloxane composition. It may be 20 parts by mass or less.
- the handleability of the curable composition can be improved.
- the shape of the cured product formed from the curable composition can be easily controlled, and for example, the formation of a cured product having a large thickness can be facilitated.
- the curable polyorganosiloxane composition of the present invention is colored because it has a pigment.
- the type of pigment is not particularly limited as described above, but can be designed to include a pigment having a similar color to the applied substrate.
- the composition contains a pigment having a small color difference ( ⁇ E) from the substrate to which the composition is applied.
- the "color difference” is a quantification of the difference between two colors as a distance in a color space, and is obtained from the distance of color coordinates in the L * a * b * color system.
- L * is the lightness of the color (0 to 100)
- a * is the position between red and green (-128 to +128) of the color
- b * is the position between yellow and blue of the color (-128).
- ⁇ + 128) is parameterized.
- a method for quantifying a color difference is known to those skilled in the art, and can be quantified using a generally available spectroscopic color difference meter or color measuring color difference meter.
- the color difference ( ⁇ E) between the curable polyorganosiloxane composition and the substrate may be larger than 20, but it is preferably 20 or less because the effect of the present invention is more pronounced. If the same pigment is used for both the curable polyorganosiloxane composition and the substrate, the components other than the pigment are colorless and transparent, and there is no large difference in the concentration of the pigment, the color difference is estimated to be 20 or less. Can be done. Alternatively, even if different pigments are used for the base material and the composition, the color difference is 20 or less if it is difficult or impossible to visually determine the boundary between the two when they are brought into contact with each other and arranged side by side. Can be estimated.
- the base material to which the curable polyorganosiloxane composition of the present invention is applied is not particularly limited.
- the base material includes metals such as aluminum, copper, nickel, iron, brass, and stainless steel; polyester resins such as epoxy resin, polyethylene terephthalate, and polybutylene terephthalate (PBT) resin, polycarbonate resin, acrylic resin, polyimide resin, and phenol resin.
- Engineering plastics such as polyamide resin, polyphenylene sulfide (PPS) resin, modified polyphenylene ether (PPE) resin; glass and the like can be used.
- the wall surface of the void or the like may be subjected to a primer treatment according to a conventional method.
- the plastic material is easy to mix with a pigment.
- a dip method, a brush coating method, a spray method, a dispense method, etc. which are known to those skilled in the art, can be used.
- the applicable thickness of the composition is usually 0.01 to 3 mm, preferably 0.05 to 2 mm.
- One aspect of the present invention is (A) Step of providing the curable polyorganosiloxane composition; (B) A step of providing a base material having a color difference ( ⁇ E) of 20 or less from the composition; To a substrate of a curable polyorganosiloxane composition comprising (C) a step of applying the composition to the substrate; and (D) a step of irradiating the composition applied to the substrate with ultraviolet light. Regarding how to check the application status. By the step (D) of irradiating with ultraviolet rays, the applied state of the composition can be easily visually confirmed.
- the step of irradiating the composition comprises irradiating the surface of the composition with ultraviolet rays having a wavelength of 280 to 440 nm, preferably 300 to 420 nm, and particularly preferably 340 to 400 nm by an ultraviolet irradiation device.
- the ultraviolet irradiation device is generally available, and a commercially available black light may be used. By observing the fluorescence from the surface of the composition by irradiating with ultraviolet rays, the state of application to the substrate can be visually confirmed.
- the method according to the present invention is a method including at least the above steps (A) to (D), but may include a step of curing the composition after the step (C) or (D).
- a method for curing the composition a method different depending on the components (a) and (b) in the composition is adopted.
- the component (a) has a hydrolyzable group as a curable functional group
- the composition can be cured by the moisture in the air.
- the moisture in the air promotes the hydrolysis reaction and the composition can be cured.
- the component (a) has a group containing an unsaturated bond as a curable functional group
- the composition can be cured by heating to room temperature to 150 ° C.
- the member whose application state has been confirmed by using the method of the present invention is effectively used for electrical and electronic parts.
- it is effective for parts that are required to have light-shielding property and concealing property as parts of a part that is normally colored with a pigment, and the method of the present invention is advantageous for their production.
- composition and method of the present invention will be described more specifically through the following examples, but the present invention is not limited to the embodiments of these examples.
- Black polyorganosiloxane composition 100 parts by mass of methyldimethoxy-terminated polydimethylsiloxane (viscosity 20 Pas) as a base polymer (component (a)) and methyltrimethoxy as a cross-linking agent (component (b)).
- Example 2 White polyorganosiloxane composition A white polyorganosiloxane composition was obtained in the same manner as in Example 1 except that the pigment was changed from carbon black to 1.0 part by mass of titanium dioxide.
- Comparative Example 3 As a type of composition that cures by the addition reaction, the compositions having the formulations shown in Table 2 below were mixed in the same manner as in Example 1 to obtain a gray polyorganosiloxane composition as a uniform composition. Comparative Example 3 has the same composition as that of Example 3 except that 2,5-thiopheneylbis (5-tert-butyl-1,3-benzoxazole) as a UV tracer was not added.
- Example 1 and Comparative Example 1 were each applied on a base material of polyphenylene sulfide (PPS) resin (black) using a stainless steel spatula so as to form a 10 mm ⁇ 25 mm square.
- the applied composition was allowed to cure in an environment of 23 ° C. and 50% relative humidity for 3 days.
- the color coordinates of the composition were measured using a color difference meter similar to that of the base material, and the color difference from the base material was calculated.
- the color coordinates of the compositions of Examples and Comparative Examples 1 to 3 and the color difference from the applicable substrate are summarized in Table 4.
- the substrate was irradiated with indoor lighting (fluorescent lamp) and UV light (wavelength 375 nm).
- Example 2 and Comparative Example 2 were also applied to a base material of polybutylene terephthalate (PBT) resin (white), and the same tests as in Example 1 were performed.
- the compositions obtained in Example 3 and Comparative Example 3 were also applied on a substrate of a modified polyphenylene ether (PPE) resin (gray) and cured in an oven at 100 ° C. for 1 hour, respectively. A similar test was performed. The results of each are summarized in Table 4.
- the composition of the present invention can be used as a sealing material or a coating agent for electrical and electronic parts, which makes it easy to confirm the application state to a substrate of a similar color. Further, the method of the present invention can be incorporated into a method for manufacturing an electric / electronic part using such a sealing material or a coating agent, and is not only easily available but also useful for manufacturing a highly reliable part. be. It is particularly useful for parts that require light-shielding and concealing properties.
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Abstract
Description
特開2007-169356号公報のように、接着剤に顔料等を配合して着色することがあるが、一方で基材の種類はその色も含めて様々である。基材の種類によっては、シリコーン接着剤と基材が同系色になることもある。基材と接着剤が同系色の場合、可視光による判別では適用の状態が確認しづらいことがある。適用が均一に行われていることが確認できないと、基材との接着が不完全になる恐れがあり、製品の信頼性にも悪影響を与える。従来の接着剤では、基材と同色の接着剤を適用した場合、きちんと適用されているか確認が難しかった。時間をかけて目視で確認するか、もしくは違う色の接着剤を使うしかなかった。
特開2019-143074号公報の方法でも、混合状態を確認することはできても、均一に適用されているかどうかは判断されておらず、適用の状態を正しく評価することは困難であった。
本発明は、着色されたシリコーン接着剤であって、同系色の基材に対して均一に適用されたかの確認が容易である接着剤、及び同接着剤を用いた適用状態の確認方法を提供することを目的とする。
以下、本発明の組成物について、項目毎に詳細に説明する。なお、本明細書において、数値範囲を示す波線「~」とは、その前後に記載された数値を下限値及び上限値として含む意味で使用される。
・成分(a)
本発明の硬化性ポリオルガノシロキサン組成物は、成分(a)として、分子内に硬化性官能基を2つ以上有するポリオルガノシロキサンを少なくとも1種含む。成分(a)は、硬化性ポリオルガノシロキサン組成物のベースポリマーとして機能する。ここで、「硬化性官能基」とは、硬化反応を起こすことが可能な官能基を指す。硬化反応の機構は特に制限されず、樹脂の硬化に一般的に用いられる方法を採用することができる。硬化反応としては特に、縮合反応又は付加反応が採用される。1分子中に含まれる各々の硬化性官能基は、同じ官能基であることが望ましいが、同種の硬化反応を起こす官能基であれば、異なる種類の官能基であっても同一分子内に混在することができる。硬化性官能基は、好ましくは成分(a)の分子主鎖の両末端に少なくとも1つずつ存在する。またここで、本明細書において、成分(a)の分子主鎖とは、成分(a)の分子中で相対的に最も長い結合鎖を表す。
M:-Si(CH3)3O1/2
MH:-SiH(CH3)2O1/2
MVi:-Si(CH=CH2)(CH3)2O1/2
D:Si(CH3)2O2/2
DH:SiH(CH3)O2/2
T:Si(CH3)O3/2
Q:SiO4/2
以下、本明細書において、シロキサン化合物は、上記の構造単位を組み合わせて構築されるものであるが、上記構造単位のメチル基がフッ素のようなハロゲン、フェニル基のような炭化水素基等、他の基に置き換わったものを少なくとも部分的に含んでいてもよい。また、例えばDH 20D20と記した場合には、DH単位が20個続いた後D単位が20個続くことを意図するものではなく、各々の単位は任意に配列していてもよいことが理解される。シロキサン化合物は、T単位又はQ単位により、3次元的に様々な構造を取ることができる。よって成分(a)は、直鎖状、分岐鎖状、環状、これらの構造の組合せ等任意の分子骨格をとることができる。成分(a)は、好ましくは、直鎖状の分子骨格を有する。
(Ra)3-pRpSi-O-(Si(R)r(Ra)2-rO)n-SiRq(Ra)3-q・・・(1)
(式中、
Raは、それぞれ独立して、硬化性官能基であり、
Rは、それぞれ独立して、1価の有機基であり、
p及びqは、各々独立して、0、1又は2であり、
rは、それぞれ独立して、0、1又は2であり、
nは、23℃における粘度を0.01~50Pa・sとする数である)
で表される直鎖状ポリオルガノシロキサンが例示される。Rとしては、炭化水素基、特にアルキル基、アルケニル基、アリール基を有するものが好ましい。屈折率等の物性を制御する観点から、Rの少なくとも一部がフェニル基等のアリール基、ビニル基等のアルケニル基であってもよい。Rが全てメチルであるようなポリオルガノシロキサンが、入手の容易性から特に好ましく用いられる。硬化性官能基の位置に関しては、上記式(1)においてrが2であるポリオルガノシロキサン、すなわち、分子の両末端のみに硬化性官能基が少なくとも1つずつ存在する直鎖状ポリオルガノシロキサンが好ましい。
成分(a)は、シロキサン樹脂の硬化反応に利用可能な官能基を1分子中に2つ以上有するものである。硬化反応のタイプにより分類すると、一つの態様において、上記成分(a)は、水酸基及び加水分解可能な基からなる群より選ばれる少なくとも一つの基と結合したSi原子を2つ以上有するポリオルガノシロキサンであることができる。この場合、水酸基及び/又は加水分解可能な基が、前記式(1)の基Raに相当する硬化性官能基となる。
縮合反応を起こすタイプの成分(a)として、以上の条件を満たす好ましい例としては、両末端がメチルジメトキシシリル基、又はトリメトキシシリル基で封鎖された直鎖状のポリオルガノシロキサン等が挙げられる。このような成分(a)として利用可能なポリオルガノシロキサンは、市販されているものを利用することができる。また、公知の反応により硬化性官能基を導入したポリオルガノシロキサンを用いてもよい。
別の一態様では、上記成分(a)は、付加反応によって硬化する(メタ)アクリル基又はビニル基のような、脂肪族不飽和結合、特にアルケニル基を有する基と結合したSi原子を2つ以上有する化合物であることもできる。付加反応を起こす硬化性官能基としては、ビニル基であることがより好ましい。この場合、脂肪族不飽和基が、前記式(1)の基Raに相当する硬化性官能基となる。
縮合反応を起こすタイプの成分(a)として、以上の条件を満たす好ましい例としては、両末端がジメチルビニルシリル基で封鎖された直鎖状のポリオルガノシロキサン等が挙げられる。このような成分(a)として利用可能なポリオルガノシロキサンは、市販されているものを利用することができる。また、公知の反応により硬化性官能基を導入したポリオルガノシロキサンを用いてもよい。
本発明の硬化性組成物における架橋剤は、前記成分(a)が有する硬化性官能基との反応性を有する架橋基を1分子中に2つ以上有するものである(以下、単に「成分(b)」ということがある)。架橋剤を含むことにより、硬化性組成物から得られる硬化物の物性、例えば引張強度や弾性率が良好になる。成分(b)が有する架橋基としては、一般的にシリコーンの硬化反応に利用される反応に活性な官能基を用いることができ、前記成分(a)が有する反応性官能基に応じて決定される。例えば、前記成分(a)が有する反応性官能基が水酸基やアルコキシ基等縮合反応をすることができる官能基であるときは、架橋基としてケイ素に直接結合した水酸基又はアルコキシ基のような加水分解性基を採用することができる。前記成分(a)が有する反応性官能基がビニル基等付加反応をすることができる官能基であるときは、架橋基としてケイ素に直接結合した水素原子、即ちSi-H基を採用することができる。成分(b)が1分子あたりに有する架橋基の数は、成分(a)間に架橋構造を形成するため2つ以上であることが必要であるが、架橋反応により網目状構造をもたらすため、3個以上であることが好ましい。各々の架橋基は、同一のケイ素原子に結合していてもよいし、異なるケイ素原子に結合していてもよい。
前記成分(a)が縮合型の反応を起こすポリオルガノシロキサンであるとき、成分(b)は、Si原子と結合した水酸基又は加水分解性基を少なくとも2個有する化合物(ただし、前記成分(a)に該当するものを除く)又はその部分加水分解縮合物である。加水分解性基としては、メトキシ基、エトキシ基、プロポキシ基、ブトキシ基のようなアルコキシ基;2-メトキシエトキシ基、2-エトキシエトキシ基のような置換アルコキシ基;イソプロペノキシ基のようなエノキシ基、メチルエチルケトオキシム基のようなケトキシマト基、アセトキシ基等が例示され、互いに同一であっても異なっていてもよい。各々の加水分解性基は、同一のケイ素原子に結合していてもよいし、異なるケイ素原子に結合していてもよい。例えば、Si原子と結合した水酸基又は加水分解性基が、シロキサン結合で連結された構造を有する化合物を架橋剤として用いることもできる。加水分解性基以外の、ケイ素原子に結合する基は、各々独立して1価の有機基であることができる。1価の有機基は、対応するケイ素化合物を入手しやすいことから、炭化水素基が好ましく、特にメチル基、ビニル基、フェニル基であることが好ましい。
R1 aSi(OR2)4-a (2)
(式中、R1は、それぞれ独立して、置換又は非置換の1価の炭化水素基であり、R2は、それぞれ独立して、水素原子又は1価の有機基であり、aは、0、1又は2である)
で表される有機ケイ素化合物又はその部分加水分解縮合物を挙げることができる。R2は、それぞれ独立して、水素原子又は1価の有機基である。1価の有機基は、1価の炭素を含有する基を意味する。かかる1価の有機基としては、特に限定されないが、1価の炭化水素基が挙げられる。炭化水素基は上記と同意義である。
であることが好ましく、より好ましくは、CH3-又はC2H5-である。
成分(b)としては、基R2を2つ以上有する環状のシロキサンであることもできる。この場合において、基R2は、シロキサン環を形成するケイ素原子に直接結合していてもよいし、していなくてもよい。環状のシロキサンは、環員数が6~10であることが好ましく、8であることがより好ましい。すなわち、Si-Oからなる単位が3~5つ、特に4つ含まれる環を形成していることが好ましい。
成分(a)がビニル基等の不飽和基を硬化性官能基として有しているときは、成分(b)の架橋基としては、Si-H結合が挙げられる。そのような架橋基を有する架橋剤としては、水素基を含有するシロキサンである、ハイドロジェンポリオルガノシロキサンが用いられる。ハイドロジェンポリオルガノシロキサンは、Si-H結合を有するシロキサン化合物であり、架橋剤となる成分である。ハイドロジェンポリオルガノシロキサンは、代表的には、下記式(3):
(Rb)x(Rc)ySiO(4-x-y)/2 (3)
(式中、
Rbは、水素原子であり、
Rcは、C1-6アルキル基(例えば、メチル、エチル、プロピル、ブチル、ペンチル、ヘキシル、好ましくはメチル)又はフェニル基であり;
xは、1又は2であり;
yは、0~2の整数であり、ただし、x+yは1~3である)
で示される単位を分子中に2個以上有する。
本発明の硬化性組成物における硬化触媒は、前記成分(a)と成分(b)との架橋反応を触媒しうる化合物である(以下、単に「成分(c)」ということがある)。前記成分(a)と成分(b)との架橋反応が縮合反応である場合は縮合触媒として知られているものを、前記成分(a)と成分(b)との架橋反応が付加反応である場合は付加硬化触媒を、それぞれ用いることができる。
成分(c)としての縮合触媒は、上記成分(a)と成分(b)との加水分解縮合を促進する成分である。縮合触媒としては、金属系触媒、有機酸系触媒、無機酸系触媒、塩基系触媒等を用いることができる。組成物の硬化速度の観点から、縮合触媒としては金属系触媒であることが好ましい。
前記成分(a)及び(b)が付加反応により架橋反応を起こす組合せである場合には、硬化触媒として付加硬化型の触媒が用いられる。代表的な例として、白金触媒が挙げられる。白金触媒は、前記成分(b)の硬化性官能基と前記成分(b)の水素基を反応させ、硬化物を得るための硬化触媒である。この白金化合物としては、塩化白金酸、白金オレフィン錯体、白金ビニルシロキサン錯体、白金リン錯体、白金アルコール錯体、白金黒等が例示される。その配合量は、前記成分(a)に対し、白金元素として0.1~1000ppmとなる量である。0.1ppmより少ないと十分に硬化せず、また1000ppmを超えても特に硬化速度の向上は期待できない。また、用途によってはより長いポットライフを得るために、反応抑制剤の添加により、触媒の活性を抑制することができる。公知の白金族金属用の反応抑制剤として、2-メチル-3-ブチン-2-オール、1-エチニル-2-シクロヘキサノール等のアセチレンアルコール、マレイン酸ジアリルが挙げられる。
本発明の硬化性組成物には、着色剤としての顔料が含まれる(以下、単に「成分(d)」ということがある)。顔料は、本発明の硬化性組成物に含まれる他の成分と反応性を有さない、有色の無機物又は有機物で、一般に顔料として扱われているものであれば、公知のものを用いることができる。ここで「有色」とは、少なくとも一部の可視光線の吸収又は散乱が起こること、すなわち透明でないことを意味する。顔料は天然由来のものであってもよく、人工的に合成又は調製されたものであってもよい。ただし、顔料自体が蛍光を発しないものである。
本発明の硬化性組成物には、UVトレーサーが含まれる(以下、単に「成分(e)ということがある」)。UVトレーサーは、紫外線を吸収して蛍光を発する化合物である。UVトレーサーとしては、440nmより短い波長の光を吸収し、蛍光、特に青~紫色の蛍光を発する無色の化合物が好ましい。UVトレーサーとしては、例えば、2,5-チオフェンジイルビル(5-tert-ブチル-1,3-ベンゾオキサゾール)のようなベンゾオキサゾール誘導体、スチルベン誘導体、イミダゾール誘導体、クマリン誘導体、ローダミンのようなフルオレセイン誘導体等の一般的に知られている化合物を使用し得る。具体的な市販品としては、BASF社製のTinopal OB等が挙げられる。
本発明の硬化性ポリオルガノシロキサンは、上記成分(a)ないし(e)を含有するものである。特に、硬化方法による分類により、湿気硬化型と付加硬化型とに分類することができる。
湿気(水分)により硬化するタイプのポリオルガノシロキサン組成物は、上記成分(a)として縮合反応を起こす硬化性官能基を有するポリオルガノシロキサンを、上記成分(b)としてSi原子と結合した水酸基又は加水分解性基を少なくとも2個有する化合物を、上記成分(c)として縮合触媒を、それぞれ有する組成物である。
特に、前記(a)が、1分子中に2個以上の水酸基及び/又はアルコキシ基を有するポリオルガノシロキサンであり、前記(b)が、式R1 aSi(OR2)4-a(ここで、R1は、それぞれ独立して1価の有機基であり、R2は、それぞれ独立して水素原子又は1価の有機基であり、aは、0、1又は2である)で表されるシラン又はその加水分解縮合物であり、前記(c)が、縮合触媒である、硬化性ポリオルガノシロキサン組成物が例として挙げられる。
不飽和結合への付加反応により硬化するタイプのポリオルガノシロキサン組成物は、上記成分(a)として付加反応を起こす硬化性官能基を有するポリオルガノシロキサンを、上記成分(b)としてポリオルガノハイドジェンシロキサンを、上記成分(c)として白金触媒を、それぞれ有する組成物である。
特に、前記(a)が、1分子中に2個以上のアルケニル基を有するポリオルガノシロキサンであり、前記(b)が、1分子中に3個以上のケイ素原子に結合した水素原子を有するハイドロジェンポリオルガノシロキサンであり、前記(c)が、白金化合物である、硬化性ポリオルガノシロキサン組成物が例として挙げられる。
硬化性ポリオルガノシロキサン組成物は、充填剤をさらに含んでもよい。充填剤としては、煙霧質シリカ、焼成シリカ、シリカエアロゲル、沈澱シリカ、珪藻土、粉砕シリカ、溶融シリカ、石英粉末、煙霧質酸化チタン、酸化鉄、酸化亜鉛、酸化チタン、酸化アルミニウム等の酸化物;これらの表面をトリメチルクロロシラン、ジメチルジクロロシラン、ヘキサメチルジシラザン、オクタメチルシクロテトラシロキサン等の疎水化剤で処理したもの;炭酸カルシウム、炭酸マグネシウム、炭酸亜鉛等の炭酸塩;アルミノケイ酸、ケイ酸カルシウム等のケイ酸塩;タルク;グラスウール、マイカ微粉末等の複合酸化物;カーボンブラック、銅粉、ニッケル粉等の導電性充填剤;ポリメチルシルセスキオキサン、ポリスチレン、ポリ塩化ビニル、ポリプロピレン等の合成樹脂粉末;アスベスト、ガラス繊維、有機繊維等の繊維質充填剤が例示される。これら充填剤は、塗布作業性と、硬化して得られるゴム状弾性体に必要な物性に応じて選択される。
硬化性ポリオルガノシロキサン組成物は、接着付与剤をさらに含んでもよい。接着付与剤は、組成物の硬化物の、ガラス、金属、プラスチック等の基材への密着性を向上させる成分である。前述の架橋剤における加水分解可能な基以外の官能基を有する化合物を、接着付与剤として用いることもできる。具体的には、アミノ基含有シラン、イソシアヌレート、カルバシラトラン化合物が挙げられる。さらに具体的な例として、ビニルトリメトキシシラン、ビニルトリエトキシシラン、3-グリシドキシプロピルトリメトキシシラン、3-グリシドキシプロピルトリエトキシシラン、3-グリシドキシプロピルメチルジメトキシシラン、3,4-エポキシシクロヘキシルエチルトリメトキシシランン、3-アクリロキシプロピルトリメトキシシラン、3-メタクリロキシプロピルトリメトキシシラン、3-アクリロキシプロピルメチルジメトキシシラン、3-メタクリロキシプロピルメチルジメトキシシラン、3-メタクリロキシプロピルメチルジエトキシシラン等が挙げられる。
硬化性ポリオルガノシロキサン組成物は、前記成分(a)及び(b)に該当しないシロキサン樹脂をさらに含んでもよい。そのような樹脂は、粘度を調整するための希釈剤としても用いることができる。そのようなシロキサン樹脂としては、下記式(4):
(Ra)3-pRpSi-O-(SiR2O)n-SiR3・・・(4)
(式中、Ra、R、p、nは、式(1)において定義したとおりである)
で示されるような、1つだけ硬化性官能基を有するシロキサンや、式(5):
R3Si-O-(SiR2O)n-SiR3・・・(5)
(式中、R、nは、式(1)において定義したとおりである)
で示される、硬化性官能基を有さないシロキサンを用いることができる。このようなシロキサン樹脂を用いることで、硬化性ポリオルガノシロキサン組成物を硬化させたときの硬度を制御することや、組成物の粘度を制御することができ、取り扱い性や要求される物性に対して広く対応することができる。
硬化性ポリオルガノシロキサン組成物は、溶剤を含んでいてもよい。この場合、硬化性ポリオルガノシロキサン組成物は、その用途、目的に応じて適当な溶剤に所望の濃度に溶解して使用し得る。上記溶剤の濃度は、例えば、硬化性ポリオルガノシロキサン組成物100質量部に対して、80質量部以下であってもよく、50質量部以下であってもよく、30質量部以下であってもよく、20質量部以下であってもよい。硬化性組成物の粘度を調整する観点からは、溶剤を含むことが好ましい。溶剤を含むことにより、硬化性組成物の取り扱い性が良好になり得る。また、硬化性組成物から形成される硬化物の形状のコントロールが容易になり得、例えば厚みの大きな硬化物の形成が容易になり得る。
△E={(L*(b)-L*(c))2+(a*(b)-a*(c))2+(b*(b)-b*(c))2}1/2
により求めることができる。ここで、L*は当該色の明度(0~100)、a*は当該色の赤-緑間の位置(-128~+128)、b*は当該色の黄色-青間の位置(-128~+128)をパラメーター化したものである。
硬化性ポリオルガノシロキサン組成物と基材との色差(ΔE)は、20より大きくてもよいが、本発明の効果がより顕著に表れるため、20以下であることが好ましい。硬化性ポリオルガノシロキサン組成物及び基材の両者とも同じ顔料を用いており、顔料以外の成分が無色透明であり、かつ、顔料の濃度に大きな差がなければ、色差は20以下と推定することができる。あるいは、基材と組成物とで異なる顔料を用いていても、両者を接触させて並べたときに両者の境界を目視で判断することができないか困難である状態であれば、色差は20以下と推定することができる。
本発明の硬化性ポリオルガノシロキサン組成物が適用される基材は、その材質に特に制限はない。基材としては、アルミニウム、銅、ニッケル、鉄、黄銅、ステンレス等の金属;エポキシ樹脂、ポリエチレンテレフタレート、ポリブチレンテレフタレート(PBT)樹脂等のポリエステル樹脂、ポリカーボネート樹脂、アクリル樹脂、ポリイミド樹脂、フェノール樹脂、ポリアミド樹脂、ポリフェニレンサルファイド(PPS)樹脂、変性ポリフェニレンエーテル(PPE)樹脂等のエンジニアリングプラスチック;ガラス等を使用することができる。また、必要に応じて、空隙の壁面等に対して常法に従ってプライマー処理を施してもよい。ただし、硬化性ポリオルガノシロキサン組成物と同系色の基材とするために、顔料を混合させることが容易なプラスチック材料であることが好ましい。
(A)前記硬化性ポリオルガノシロキサン組成物を提供する工程;
(B)該組成物との色差(△E)が20以下である基材を提供する工程;
(C)該基材に該組成物を適用する工程;及び
(D)該基材に適用された該組成物に紫外線を照射する工程
を含む、硬化性ポリオルガノシロキサン組成物の基材への適用状態を確認する方法に関する。紫外線を照射する工程(D)によって、組成物の適用状態を目視により簡便に確認することができる。紫外線を照射する工程は、組成物表面に紫外線照射装置により波長280~440nm、好ましくは300~420nm、特に好ましくは340~400nmの紫外線を照射することからなる。紫外線照射装置は一般に利用可能であり、市販のブラックライトを用いてもよい。紫外線を照射することで組成物表面からの蛍光を観察することにより、基材への適用状態を目視により確認することができる。
ベースポリマー(成分(a))としてのメチルジメトキシ末端ポリジメチルシロキサン(粘度20Pas)を100質量部、架橋剤(成分(b))としてのメチルトリメトキシシランを1.1質量部、接着付与剤を兼ねる架橋剤として3-アミノプロピルトリメトキシシラン0.44質量部及びトリス[3-(トリメトキシシリル)プロピル]イソシアヌレート0.66質量部、触媒(成分(c))としてジブチルスズジラウレート0.38質量部、顔料(成分(d))としてカーボンブラック0.5質量部、UVトレーサー(成分(e))として2,5-チオフェンジイルビス(5-tert-ブチル-1,3-ベンゾオキサゾール)を0.013質量部、更に充填材として煙霧質シリカ14質量部及び希釈剤としてジメチルシロキサン(粘度0.1Pas)18質量部を、プラネタリーミキサーを用いて混合し、均一な組成物として黒色のポリオルガノシロキサン組成物を得た。
UVトレーサーとしての2,5-チオフェンジイル ビス(5-tert-ブチル-1,3-ベンゾオキサゾール)を加えなかったこと以外は実施例1と同様にして、黒色のポリオルガノシロキサン組成物を得た。
顔料をカーボンブラックから二酸化チタン1.0質量部に変えたこと以外は、実施例1と同様にして、白色のポリオルガノシロキサン組成物を得た。
UVトレーサーとしての2,5-チオフェンジイル ビス(5-tert-ブチル-1,3-ベンゾオキサゾール)を加えなかったこと以外は実施例2と同様にして、白色のポリオルガノシロキサン組成物を得た。実施例1、2及び比較例1、2における組成物の組成を表1に纏める。
付加反応により硬化するタイプの組成物として、下記表2に示す配合の組成物を実施例1と同様に混合し、均一な組成物として灰色のポリオルガノシロキサン組成物を得た。比較例3は、UVトレーサーとしての2,5-チオフェンジイル ビス(5-tert-ブチル-1,3-ベンゾオキサゾール)を加えなかったこと以外は実施例3と同じ配合である。
各実施例及び比較例の組成物を適用する基材として、ポリフェニレンサルファイド(PPS)樹脂(ポリプラスチック社製、黒色)、ポリブチレンテレフタラート(PBT)樹脂(ポリプラスチック社製、白色)、変性ポリフェニレンエーテル(PPE)樹脂(SABIC社製、灰色)を準備した。コニカミノルタ社製色彩色差計CR-400を用いて測定した各基材の色座標を、以下の表3に示す。
実施例2及び比較例2で得た組成物についてもそれぞれ、ポリブチレンテレフタラート(PBT)樹脂(白色)の基材上に適用し、実施例1についてと同様の試験を行った。
実施例3及び比較例3で得た組成物についてもそれぞれ、変性ポリフェニレンエーテル(PPE)樹脂(灰色)の基材上に適用し、100℃、1時間オーブン中で硬化させ、実施例1についてと同様の試験を行った。それぞれの結果を表4に纏める。
Claims (7)
- (a)1分子中に硬化性官能基を2つ以上有するポリオルガノシロキサン;
(b)前記(a)の硬化性官能基との反応性を有する架橋基を1分子中に2つ以上有する架橋剤;
(c)前記(a)及び(b)の架橋反応を触媒し得る、硬化触媒;
(d)それ自体が蛍光を発しない顔料;及び
(e)UVトレーサーを含む、硬化性ポリオルガノシロキサン組成物。 - 前記(a)が、1分子中に2個以上の水酸基及び/又は加水分解性基を有するポリオルガノシロキサンであり、前記(b)が、1分子中に2個以上の水酸基及び/又は加水分解性基を有するケイ素化合物又はその加水分解縮合物であり、前記(c)が、縮合触媒である、請求項1記載の硬化性ポリオルガノシロキサン組成物。
- 前記(a)が、1分子中に2個以上のアルケニル基を有するポリオルガノシロキサンであり、前記(b)が、1分子中に3個以上のケイ素原子に結合した水素原子を有するハイドロジェンポリオルガノシロキサンであり、前記(c)が、白金化合物である、請求項1記載の硬化性ポリオルガノシロキサン組成物。
- 1液型の組成物である、請求項1~3のいずれか一項記載の硬化性ポリオルガノシロキサン組成物。
- (d)顔料が、カーボンブラック、酸化チタン、酸化鉄及びこれらの混合物からなる群より選択される、請求項1~4のいずれか一項記載の硬化性ポリオルガノシロキサン組成物。
- 該組成物との色差(ΔE)が20以下である基材の接着用の、請求項1~5のいずれか一項記載の硬化性ポリオルガノシロキサン組成物。
- 請求項1~6のいずれか一項記載の硬化性ポリオルガノシロキサン組成物を提供する工程;
該組成物との色差(△E)が20以下である基材を提供する工程;
該基材に該組成物を適用する工程;及び
該基材に適用された該組成物に紫外線を照射する工程
を含む、硬化性ポリオルガノシロキサン組成物の基材への適用状態を確認する方法。
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FR3139576A1 (fr) * | 2022-09-09 | 2024-03-15 | C.O.P. | Composition de silicone pour l’impression en trois dimensions d’un objet |
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