TW201641655A - Silicone-based pressure-sensitive adhesive, and laminate having silicone-based pressure-sensitive adhesive layer - Google Patents

Abstract

This silicone pressure-sensitive adhesive comprises at least: (A) (A1) an organopolysiloxane having a molecular chain end of which at least 25 mol% is blocked with a hydroxy group bonded to a silicon atom or a hydrolyzable group bonded to a silicon atom, and having at least an average of one alkenyl group in each molecule, or a mixture of (A2) an organopolysiloxane having a molecular chain end that is blocked with a hydroxy group bonded to a silicon atom or a hydrolyzable group bonded to a silicon atom, and (A3) an organopolysiloxane having a molecular chain end that is blocked with a triorganosiloxy group and having at least an average of one alkenyl group in each molecule; (B) an organopolysiloxane having, in each molecule, at least three hydrogen atoms bonded to a silicon atom; and (C) a catalyst for a hydrosilylation reaction. The silicone pressure-sensitive adhesive forms a pressure-sensitive adhesive layer that exhibits little transfer to an adherend when rereleased.

Description

Polyoxygen-based pressure-sensitive adhesive and laminated body having poly-n-oxide pressure-sensitive adhesive layer

The present invention relates to a polyfluorene-based pressure-sensitive adhesive and a laminate having a pressure-sensitive adhesive layer formed using the pressure-sensitive adhesive.

A protective film for temporarily protecting such a cover glass or a touch panel for covering a display portion of a portable computer such as a mobile phone, a portable music player, a portable personal computer, or the like (Refer to Patent Document 1).

Such a protective film is required to adhere to an adherend such as a cover glass or a touch panel when the manufacturing process is moved, and the adhesive force can be easily peeled off during use. Further, it is also required that the pressure-sensitive adhesive layer does not transfer to the adherend at the time of re-peeling.

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open Publication No. 2007-045102

An object of the present invention is to provide a laminate which is formed by a pressure-sensitive adhesive layer which is formed by a pressure-sensitive adhesive layer which is less transferred to an adherend during re-peeling, and which has less transfer of a pressure-sensitive adhesive layer.

The polyfluorene-based pressure-sensitive adhesive of the present invention is characterized by comprising at least: (A) at least 25 mol% of the end of the molecular chain of (A1) via a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom An organopolysiloxane having a chain of at least one alkenyl group in one molecule, or an organopoly group terminated at the end of the (A2) molecular chain via a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom 100 parts by mass of a mixture of a halogenated alkane and an (A3) molecular chain having a terminal end with a triorganosalkoxy group and having at least one alkenyl group in at least one molecule; (B) having at least 3 in one molecule An organic polyoxane of a hydrogen atom bonded to a ruthenium atom {relative to 1 mole of the alkenyl group contained in the component (A), the hydrogen atom bonded to the ruthenium atom contained in the component is 0.5 mole Above and below 20 moles}; and (C) catalyst for hydrogenation reaction (the amount which promotes the hydrogenation reaction of the present composition).

Further, the laminate of the present invention is characterized in that it comprises a support and a pressure-sensitive adhesive layer formed by a hydrogenation reaction of the above-mentioned polyfluorene-based pressure-sensitive adhesive.

The polyfluorene-based pressure-sensitive adhesive of the present invention has a feature of forming a pressure-sensitive adhesive layer which is less transferred to the adherend during re-peeling, and the laminate of the present invention has less pressure-sensitive adhesive layer transfer. feature.

1‧‧‧Support

2‧‧‧pressure layer

BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a cross-sectional view showing a laminate of the present invention.

First, the polyfluorene-based pressure-sensitive adhesive of the present invention will be described in detail.

(A) at least 25 mol% of the end of the molecular chain of the component (A1) is organically terminated by a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom and having at least one alkenyl group in one molecule. Polyoxyalkylene, or (A2) molecular chain end via a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group-bound organopolyoxane bonded to a ruthenium atom and (A3) molecular chain terminal via triorganoindole A mixture of an alkoxy-terminated and organopolyoxyalkylene having at least one alkenyl group in one molecule.

The component (A1) is an organopolysiloxane having at least one average, preferably at least 1.5, or at least 2 alkenyl groups in one molecule. This is because when the alkenyl group in the component (A1) is at least the above lower limit, the pressure-sensitive adhesive is sufficiently crosslinked in a short time. The alkenyl group in the component (A1) may, for example, be a vinyl group, an allyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a pentenyl group or an undecenyl group. The alkenyl group having 2 to 12 carbon atoms such as dodecenyl group is preferably a vinyl group or a hexenyl group. The bonding position of the alkenyl group is not limited, and may be bonded to a ruthenium atom at the end of the molecular chain and/or a ruthenium atom in the molecular chain. The organic group bonded to the ruthenium atom other than the alkenyl group in the component (A1) may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group or an isopentyl group. , neopentyl, heptyl, octyl, decyl, decyl, undecyl, dodecyl and other alkyl groups having 1 to 12 carbon atoms; phenyl, tolyl, xylyl and other carbon number 6~ An aryl group having 12 to 12 carbon atoms such as a benzyl group or a phenethyl group; preferably a methyl group or a phenyl group.

The molecular structure of the component (A1) is linear or partially linear, and has at least 25 mol%, preferably 50 mol%, or 100 mol% of the terminal group of the molecular chain. A hydroxyl group bonded to a bond or a hydrolyzable group bonded to a ruthenium atom. This is because when the molecular chain terminal group is at least the above lower limit, the resulting pressure-sensitive adhesive layer is less likely to be transferred. The hydrolyzable group bonded to the ruthenium atom may, for example, be an alkoxy group such as a methoxy group, an ethoxy group or a propoxy group; an amineoxy group such as a dimethylamino group or a diethylamino group; a methoxy group such as an oxy group, a octyloxy group or a benzamidine group; an oxy group such as an isopropenyloxy group or a 1-ethyl-2-methylvinyloxy group; a dimethylamino group and a diethylamine; An amine group such as a butylamine group or a cyclohexylamino group; an amide group such as N-methylacetamidoamine, N-ethylethylammoniumamine or N-methylbenzamide; dimethyl group; a ketone oxime group such as a ketone oxime group, a methyl ethyl ketone oxime group or a diethyl ketone fluorenyl group; a halogen atom such as fluorine, chlorine or bromine. Examples of the group at the end of the other molecular chain include the above-mentioned alkyl group, alkenyl group, aryl group, and aralkyl group.

The (A1) component is exemplified by a dimethyl methoxy oxane-methylvinyl fluorene copolymer which is terminated with a dimethyl hydroxy decyloxy group at both ends of the molecular chain, and a dimethyl hydroxy group at both ends of the molecular chain. a decyloxy-terminated dimethyl methoxy oxane-diphenyl sulfoxane-methylvinyl fluorene copolymer, and a mixture of two or more of these organic polyoxy siloxanes.

The viscosity of the component (A1) is not limited, and it is preferably a viscosity at 25 ° C of more than 10,000 mPa ‧ s, a 50,000 mPa ‧ s or more, or a raw rubber at 25 ° C. This is because if the viscosity of the component (A1) is at least the lower limit of the above range, the smoothness of the coating film is improved. Further, the viscosity of the component (A1) at 25 ° C can be measured by a rotational viscometer in accordance with JIS K7117-1. Further, when the component (A1) is in the form of a raw rubber at 25 ° C, it is a plasticity measured by the method specified in JIS K 6249.

Further, the component (A2) is an organopolysiloxane having at least one average, preferably at least 1.5, or at least two alkenyl groups in one molecule. This is because when the alkenyl group in the component (A2) is at least the above lower limit, the pressure-sensitive adhesive is sufficiently crosslinked in a short time. The molecular structure of the component (A2) is linear or partially linear, and the terminal of the molecular chain is terminated by a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom. The hydrolyzable group bonded to the ruthenium atom can be exemplified by the same groups as described above. The organic group bonded to the ruthenium atom in the component (A2) may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group, an isopentyl group or a neopentyl group. Heptyl, octyl, decyl, decyl, undecyl, dodecyl and the like having an alkyl group of 1 to 12; vinyl, allyl, butenyl, pentenyl, hexenyl, Heptenyl, octenyl, pentenyl, undecenyl, dodecenyl and other alkenyl groups having 2 to 12 carbons; phenyl, tolyl, xylyl and the like having 6 to 12 carbon atoms a benzyl group such as a benzyl group or a phenethyl group having 7 to 12 carbon atoms.

As such a component (A2), a dimethylpolysiloxane having a terminal end of a molecular chain terminated by a dimethyl hydroxy decyloxy group and a terminal of a molecular chain terminated by a diphenyl hydroxy decyloxy group may be exemplified. Methyl polyoxyalkylene, a dimethyl methoxy alkane-methylphenyl decane copolymer terminated by a dimethyl vinyl alkoxy group at both ends of the molecular chain, and a dimethyl hydroxy hydrazine at both ends of the molecular chain Alkoxy-terminated dimethyl methoxy oxane-diphenyl fluorene copolymer, dimethyl methoxy oxane-methyl phenyl oxime terminated at both ends of the molecular chain via diphenyl hydroxy decyloxy An alkane copolymer, a dimethyl methoxy alkane-methylvinyl decane copolymer terminated by a dimethyl hydroxy decyloxy group at both ends of the molecular chain, and a terminal end of the molecular chain terminated by a dimethyl hydroxy decyloxy group a dimethyl oxoxane-methylphenyl fluorene-methylvinyl decane copolymer, dimethyl methoxy oxane-diphenyl terminated at both ends of the molecular chain via dimethyl hydroxy decyloxy a methoxy oxane-methylvinyl fluorene copolymer, a methyl vinyl polyoxyalkylene terminated by a dimethyl hydroxy decyloxy group at both ends of the molecular chain, and a dimethyl hydroxy decane oxygen at both ends of the molecular chain a methyl-terminated methoxane-methylphenyl decane copolymer at the base end, a methyl vinyl fluorene-diphenyl fluorene terminated by a dimethyl hydroxy decyloxy group at both ends of the molecular chain An alkane copolymer, and a dimethyl methoxy alkane-methylvinyl decane copolymer terminated by a dimethyl hydroxy decyloxy group at both ends of the molecular chain, and the organic polymerization a mixture of two or more of oxoxanes.

The viscosity of the component (A2) is not limited, and it is preferably a viscosity at 25 ° C of 100 mPa ‧ s or more, 200 mPa ‧ s or more, or 500 mPa ‧ s or more. On the other hand, the upper limit of the viscosity of the component (A2) is not limited, and may be a viscosity at 25 ° C of more than 10,000 mPa ‧ s, a 50,000 mPa ‧ s or more, or a raw rubber at 25 ° C, or The viscosity at 25 ° C is 10,000 mPa ‧ s or less, 5000 mPa ‧ s or less, or 3000 mPa ‧ s or less. This is because if the viscosity of the component (A2) is at least the above lower limit, sufficient adhesion can be obtained. Further, the viscosity of the component (A2) at 25 ° C can be measured by a rotational viscometer in accordance with JIS K7117-1. Further, when the component (A2) is in the form of a raw rubber at 25 ° C, the degree of plasticization can be measured in accordance with the method specified in JIS K 6249.

Further, the component (A3) is an organopolyoxyalkylene having at least one average, preferably at least 1.5, or at least an average of two alkenyl groups in one molecule. This is because when the alkenyl group in the component (A3) is at least the above lower limit, the pressure-sensitive adhesive is sufficiently crosslinked. The molecular structure of the component (A3) is linear or partially branched and linear, and the terminal of the molecular chain is terminated by a triorganodecyloxy group. As the alkenyl group in the component (A3), vinyl, allylate can be exemplified An alkenyl group having 2 to 12 carbon atoms such as a butyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a pentenyl group, an undecenyl group or a dodecenyl group; Vinyl, hexenyl. The bonding position of the alkenyl group is not limited, and may be bonded to a ruthenium atom at the end of the molecular chain and/or a ruthenium atom in the molecular chain. The group bonded to the ruthenium atom other than the alkenyl group in the component (A3) may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group or an isopentyl group. Neopentyl, heptyl, octyl, decyl, decyl, undecyl, dodecyl and other alkyl groups having 1 to 12 carbon atoms; phenyl, tolyl, xylyl and other carbon numbers 6 to 12 An aryl group; a aralkyl group having 7 to 12 carbon atoms such as a benzyl group or a phenethyl group; preferably a methyl group, a phenyl group or a hydroxyl group.

As such a component (A3), a dimethylpolysiloxane having a terminal end of a molecular chain terminated by a dimethylvinyl alkoxy group and a terminal end of the molecular chain terminated with a diphenylvinyl decyloxy group can be exemplified. a dimethyl polysiloxane, a dimethyl methoxy oxane-methyl phenyl siloxane copolymer terminated by a dimethyl vinyl alkoxy group at both ends of the molecular chain, and a dimethyl group at both ends of the molecular chain Vinyl decyloxy-terminated dimethyl methoxy oxane-diphenyl decane copolymer, dimethyl methoxy oxane-methyl benzene terminated at both ends of the molecular chain via diphenyl vinyl decyloxy a quinone oxyalkylene copolymer, a dimethyl methoxy oxane-methylvinyl decane copolymer terminated by a dimethylvinyl decyloxy group at both ends of the molecular chain, and a dimethyl vinyl group at both ends of the molecular chain a decyloxy-terminated dimethyl methoxy oxane-methylphenyl fluorene-methylvinyl decane copolymer, a dimethyl group terminated at both ends of the molecular chain by dimethylvinyl decyloxy a decane-diphenyl sulfoxane-methylvinyl fluorene copolymer, a methyl vinyl polyoxyl terminated by a trimethyl decyloxy group at both ends of the molecular chain a methyl vinyl fluorene-methyl phenyl siloxane copolymer terminated by a trimethyl decyloxy group at both ends of the molecular chain, and a methyl methacrylate terminated with a trimethyl decyloxy group at both ends of the molecular chain a sulfonium-diphenyl decane copolymer, and a dimethyl methoxy oxane-methylvinyl fluorene copolymer terminated with a trimethyl decyloxy group at both ends of the molecular chain, and the organic A mixture of two or more polyoxyalkylenes.

The viscosity of the component (A3) is not limited, and the viscosity at 25 ° C is preferably 100 mPa ‧ or more and 10,000 mPa ‧ or less, 150 mPa ‧ or more and 5000 mPa ‧ s Lower, or 200mPa‧s or more and 3000mPa‧s or less. The reason for this is that if the viscosity of the component (A3) is at least the lower limit of the above range, a sufficient adhesive force can be obtained. On the other hand, if it is at most the upper limit of the above range, the transfer of the pressure-sensitive adhesive layer is less likely to occur. Further, the viscosity of the component (A3) at 25 ° C can be measured by a rotational viscometer in accordance with JIS K7117-1.

The content of the component (A2) and the component (A3) is not limited, and the content of the component (A2) is preferably 5 to 99% by mass, 10 to 95% by mass, or 30 to 90% by mass of the component (A). The reason for this is that if the content of the component (A2) is at least the lower limit of the above range and not more than the upper limit of the above range, the transfer is less likely to occur.

The component (B) is a crosslinking agent of the pressure-sensitive adhesive, and is an organopolyoxane having at least three hydrogen atoms bonded to a ruthenium atom in one molecule. The bonding position of the hydrogen atom bonded to the ruthenium atom is not limited, and may be bonded to a ruthenium atom at the end of the molecular chain and/or a ruthenium atom in the molecular chain. The group bonded to the ruthenium atom other than the hydrogen atom in the component (B) may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a pentyl group or an isopentyl group. Neopentyl, heptyl, octyl, decyl, decyl, undecyl, dodecyl and other alkyl groups having 1 to 12 carbon atoms; phenyl, tolyl, xylyl and other carbon numbers 6 to 12 An aryl group; an aralkyl group having 7 to 12 carbon atoms such as a benzyl group or a phenethyl group; a hydroxyl group; an alkoxy group having 1 to 3 carbon atoms such as a methoxy group, an ethoxy group or a propoxy group; The isopropenyloxy group is preferably a methyl group or a phenyl group. The molecular structure of the component (B) is not limited, and examples thereof include a linear chain, a partially branched linear chain, a branched chain, a cyclic resin, and a resin. Preferably, the chain is linear and partially branched. Straight chain.

As the component (B), a methylhydropolysiloxane having a terminal end of a molecular chain blocked by a trimethylsulfanyloxy group, and a dimethyloxy group terminated by a trimethyldecaneoxy group at both ends of the molecular chain can be exemplified. Alkane-methylhydroquinone copolymer, dimethyl methoxy oxane-methylhydroquinone-methyl phenyl siloxane copolymer, molecularly terminated at both ends thereof via trimethyl decyloxy a dimethyl oxirane-methylhydrooxane copolymer terminated by a dimethylhydroquinoloxy group at both ends of the chain, and a dimethyl oxime terminated at both ends of the molecular chain by dimethylhydrohaloalkoxy Alkyl-methylphenyl sulfoxane-methylhydroquinone copolymer, methylphenyl sulfoxane-methylhydroquinone copolymer terminated at both ends of the molecular chain via dimethylhydroquinoloxy The formula contains: a fluorinated alkane unit represented by R ₃ SiO _1/2 , a fluorinated alkane unit represented by the formula: R ₂ HSiO _1/2 and an organic polycondensation of a oxirane unit represented by the formula: SiO _4/2 a decane resin; an organopolyoxane resin having the formula: R ₂ HSiO _1/2 represented by a fluorinated alkane unit represented by the formula: SiO _4/2 ; containing a formula: RHSiO _2/2 Oxane And two kinds or more of these organopolysiloxanes of silicon alumoxane; HSiO _3/2 organopolysiloxane represented by the siloxane silicone resin Silicone siloxane unit of: and the formula element: silicon or siloxane units represented by the formula RSiO _3/2 mixture. In the above formula, R is: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, heptyl, octyl, decyl, decyl, Alkyl group having 1 to 12 carbon atoms such as undecyl or dodecyl; aryl group having 6 to 12 carbon atoms such as phenyl, tolyl or xylyl; carbon number 7 to 12 such as benzyl and phenethyl Aralkyl group.

Further, the viscosity of the component (B) is not limited, and it is preferably in the range of 3 to 50,000 mm ² /s at 25 ° C. The reason for this is that if the dynamic viscosity of the component (B) is at least the lower limit of the above range, the volatility of the component (B) is lowered, and the composition of the pressure-sensitive adhesive obtained is stable. On the other hand, the upper limit of the above range is Hereinafter, the transfer of the pressure-sensitive adhesive layer is suppressed. Further, the dynamic viscosity of the component (B) at 25 ° C can be measured by a Ubum viscometer in accordance with JIS Z8803.

The content of the component (B) is 1 mol in total with respect to the alkenyl group contained in the component (A), and the hydrogen atom bonded to the ruthenium atom contained in the component is 0.5 mol or more and 20 mol or less. It is preferably an amount of 0.7 mol or more and 10 mol or less, or an amount of 1 mol or more and 8 mol or less. The reason for this is that if the content of the component (B) is at least the lower limit of the above range, a pressure-sensitive adhesive layer having sufficient mechanical properties can be formed, and if it is at most the upper limit of the above range, the pressure-sensitive layer is The transfer is suppressed.

The component (C) is a catalyst for hydrogenation reaction for promoting the hydrogenation reaction of the pressure-sensitive adhesive, and a platinum-based catalyst, a palladium-based catalyst, or a ruthenium-based catalyst is preferable, and a platinum-based catalyst is preferable. Make Examples of the platinum-based catalyst include chloroplatinic acid, an alcohol solution of chloroplatinic acid, a carbonyl complex of platinum, an alkenyl alkoxylate complex of platinum, and an olefin complex of platinum, especially A) The alkenyl alkoxylate complex of platinum is preferred in terms of good compatibility of the components. In the platinum alkenyl alkane complex, examples of the alkenyl alkane include 1,3-divinyltetramethyldioxane and 1,1,3,3-tetraethylene. Dimethyl dioxane.

The content of the component (C) is an amount which promotes the hydrogenation reaction of the pressure-sensitive adhesive. Specifically, it is preferably 0.1 to 1,000 ppm by mass of the catalyst metal in the component of the component (A). The amount within the range, or the amount within the range of 1 to 500 ppm. The reason is that when the content of the component (C) is at least the lower limit of the above range, the hydrogenation reaction of the pressure-sensitive adhesive is promoted. On the other hand, if the content is at most the upper limit of the above range, the pressure-sensitive adhesive layer obtained is obtained. It is not easy to cause problems such as coloring.

In order to adjust the rate of the hydrogenation reaction, (D) a hydrogenation reaction inhibitor may be contained in the pressure sensitive adhesive. As the component (D), 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, and 3-methyl-1-pentene can be exemplified. Alkynyl alcohols such as 3-ol, 2-phenyl-3-butyn-2-ol, 1-ethynyl-1-cyclohexanol; 3-methyl-3-pentene-1-yne, 3,5 - alkyne compound such as dimethyl-3-hexene-1-yne; 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetraoxane, 1,3 An alkenyl oxoxane such as 5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetraoxane; and benzotriazole.

The content of the component (D) is not particularly limited, and is preferably 5 parts by mass or less or 3 parts by mass or less based on 100 parts by mass of the component (A). On the other hand, the lower limit is 0.01 parts by mass or more, or 0.1. More than the mass. The reason for this is that when the content of the component (D) is at least the lower limit of the above range, the usable time of the coating liquid can be ensured, and if it is at most the upper limit of the above range, it can be used at a usual curing temperature. The adhesive hardens.

In order to improve the coatability of the pressure-sensitive adhesive, (E) an organic solvent may be contained therein. Examples of the organic solvent include aromatic hydrocarbon solvents such as toluene and xylene; aliphatic hydrocarbon solvents such as heptane, hexane, octane, and isoparaffin; and ester solvents such as ethyl acetate and isobutyl acetate. Diisopropyl ether, 1,4-two An ether solvent such as an alkane.

The content of the component (E) is not limited, and is preferably in the range of 10 to 3,000 parts by mass or 30 to 2,000 parts by mass based on 100 parts by mass of the total of the components (A) and (B). The reason for this is that if the content of the component (E) is at least the lower limit of the above range, the applicability of the pressure-sensitive adhesive can be improved. On the other hand, if the content is at most the upper limit of the above range, the pressure can be controlled. The film thickness of the layer is then.

In order to adjust the adhesion of the adhesive, an organic polyoxyalkylene resin containing (F) R ¹ ₃ SiO _1/2 unit (wherein R ¹ is halogen-containing) may be contained therein. The substituted or unsubstituted one-valent hydrocarbon group) and the SiO _4/2 unit, and the molar ratio of the R ¹ ₃ SiO _1/2 unit to the SiO _4/2 unit is 0.5 or more and 1.5 or less.

In the component (F), R ¹ is a halogen-substituted or unsubstituted one-valent hydrocarbon group, and examples thereof include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, and isoprene. Alkyl, neopentyl, heptyl, octyl, decyl, decyl, undecyl, dodecyl and the like having an alkyl group of 1 to 12; vinyl, allyl, butenyl, pentene a carbon having 2 to 12 carbon atoms such as a hexyl group, a hexenyl group, a heptenyl group, an octenyl group, a pentenyl group, an undecenyl group or a dodecenyl group; a carbon such as a phenyl group, a tolyl group or a xylyl group; An aryl group having 6 to 12; an aralkyl group having 6 to 12 carbon atoms such as a benzyl group or a phenethyl group; a halogenated alkyl group such as a chloromethyl group, a 3-chloropropyl group or a 3,3,3-trifluoropropyl group; It is preferably a methyl group, a vinyl group or a phenyl group. Further, the component (F) may have a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom. The hydrolyzable group may, for example, be an alkoxy group having 1 to 3 carbon atoms such as a methoxy group, an ethoxy group or a propoxy group; an ethoxy group; an isopropenyloxy group.

The component (F) essentially contains R ¹ ₃ SiO _1/2 unit and SiO _4/2 unit, and may have R ¹ ₂ SiO _2/2 unit or R ¹ SiO _3/2 unit, in (F) component. The total content of the R ¹ ₃ SiO _1/2 unit and the SiO _4/2 unit is preferably 50% by mass or more, more preferably 80% by mass or more, and particularly preferably 100% by mass, that is, only the two units are contained. .

In the component (F), the R ¹ ₃ SiO _1/2 unit is preferably in the range of 0.5 to 1.5, in the range of 0.5 to 1.0, or in the range of 0.6 to 0.9 with respect to the SiO _4/2 unit. The reason for this is that if the molar ratio is at least the lower limit of the above range, the adhesion of the pressure-sensitive adhesive layer obtained is increased. On the other hand, if the molar ratio is less than or equal to the upper limit of the above range, the resulting pressure-sensitive adhesive layer is adhered to the layer. Reduced sex.

The content of the component (F) is preferably 30 parts by mass or less, or 10 parts by mass or less based on 100 parts by mass of the component (A). The reason for this is that if the content of the component (F) is at most the upper limit of the above range, the adhesion of the resulting pressure-sensitive adhesive layer can be controlled.

Further, as long as the object of the present invention is not impaired, the pressure-sensitive adhesive may include a dimethylpolyoxane terminated at both ends of the molecular chain by a dimethylhydroquinoloxy group, and both ends of the molecular chain. Methyl phenyl polyoxyalkylene terminated by dimethylhydroquinoloxy-terminated dimethyl methoxy oxane-methylphenyl decane copolymer and terminated with dimethylhydroquinoloxy at both ends of the molecular chain a diorganopolyoxane having only a hydrogen atom bonded to a ruthenium atom at both ends of the molecular chain; toluene, xylene, hexane, heptane, acetone, methyl ethyl ketone, methyl isobutyl ketone And other organic solvents; tetramethoxy decane, tetraethoxy decane, dimethyl dimethoxy decane, methyl phenyl dimethoxy decane, methyl phenyl diethoxy decane, phenyl trimethoxy Decane, methyltrimethoxydecane, methyltriethoxydecane, vinyltriethoxydecane,allyltrimethoxydecane,allyltriethoxydecane,3-glycidoxypropyl Alkoxydecanes such as trimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane; and antioxidants, pigments, and stabilizers .

Next, the laminated body of the present invention will be described in detail by means of Fig. 1.

The laminate of the present invention comprises at least a support 1 and a pressure-sensitive adhesive layer 2 formed by subjecting the above-mentioned polyfluorene-based pressure-sensitive adhesive to a hydrogenation reaction. Such a laminate of the present invention can be used, for example, as an adhesive film.

Examples of the support 1 include a polyester resin, a polyethylene terephthalate resin, a polycarbonate resin, a polyethylene resin, and a polypropylene, in addition to an inorganic support such as a glass plate, a metal plate, or a metal foil. a plastic plate or film such as a resin, an ethylene-propylene copolymer resin, an ethylene-vinyl acetate copolymer resin, or an ethylene-ethylene acrylate copolymer resin. The thickness is not limited and is usually preferably from 10 to 3,000 μm.

In order to improve the adhesion to the polyoxynitride pressure-sensitive adhesive layer 2, the surface of the support 1 may be subjected to a primer treatment, a corona treatment, an etching treatment, or a plasma treatment, and it is particularly preferable to use a polyoxygen adhesive. The primer composition is used as a primer. As a primer composition for such a polyoxygen adhesive, it is disclosed in Japanese Laid-Open Patent Publication No. Sho 54-61242, Japanese Patent Application Laid-Open No. Hei No. Hei No. Hei. A primer composition. Further, such a primer composition for a polyoxygen adhesive can be prepared, for example, by blending a platinum-based catalyst in DOW CORNING ^(R) 7499 PSA PRIMER manufactured by Dow Corning Co., Ltd. and DOW CORNING ^(R) 7387 CROSSLINKER.

Further, the method of applying the polyoxynitride-based pressure-sensitive adhesive to the support film 1 is not limited, and examples thereof include gravure coating, lithographic coating, offset gravure, roll coating, reverse roll coating, and air knife coating. Cloth, curtain coating, corner wheel coating.

Then, a pressure-sensitive adhesive layer can be formed on the support by subjecting the polyfluorene-based pressure-sensitive adhesive to a hydrogenation reaction at room temperature or by heating. The heating condition can be set at 60 to 160 ° C for 15 seconds to 5 minutes.

In the laminate of the present invention, the thickness of the pressure-sensitive adhesive layer 2 is not limited, and is usually in the range of 1 to 1,000 μm or in the range of 5 to 500 μm.

Further, the laminate of the present invention may be obtained by directly applying the pressure-sensitive adhesive to the support to form a laminate as described above, or may be produced by a transfer method as described below. The pressure-sensitive adhesive is applied to a release film or a release paper, and a pressure-sensitive adhesive layer is formed by a hydrogenation reaction, and then bonded to the above-mentioned support.

[Examples]

The polyfluorene-based pressure-sensitive adhesive and the layered body of the present invention will be described in detail by way of examples and comparative examples. Further, the viscosity and the degree of plasticization in the examples were measured at 25 ° C. Further, the adhesion and the pressure-sensitive layer were transferred in the following manner as follows.

[viscosity]

The viscosity (mPa‧s) is a value measured in accordance with JIS K7117-1 using a rotational viscometer, and the dynamic viscosity (mm ² /s) is a value measured by a Ubum viscometer in accordance with JIS Z8803.

[degree of plasticization]

The degree of plasticization is represented by a value measured in accordance with the method specified in JIS K 6249 (a value of a load of 1 kgf applied to a 4.2 g spherical sample at 25 ° C for 3 minutes).

[adhesion]

The pressure-sensitive adhesive film was cut into a width of 25 mm, and a pressure-sensitive adhesive was applied to the tape, and this was pressure-bonded to the adherend of the glass using a 2 kgf rubber roller. Thereafter, it was allowed to stand at room temperature for 24 hours. The adhesion (gf/25 mm) was measured by a 180° peeling method using a low speed (300 mm/min) tensile tester.

[Transfer of pressure layer followed by layer]

Two protective films having a pressure-sensitive adhesive layer were cut out in a size of 3 cm × 4 cm, and crimped to both sides of a glass plate having a thickness of 1 mm using a 2 kgf rubber roller. After storing in an oven at 70 ° C and a relative humidity of 95% for 24 hours, it was taken out from the oven and cooled at room temperature. Thereafter, the protective film on both sides was peeled off, and a flashlight equipped with an LED lamp was irradiated from the back side of the glass plate at an angle of 45 degrees obliquely to visually observe the transfer of the pressure-sensitive adhesive layer. Further, by a tabletop fluorescent lamp, light was irradiated from the back side of the glass plate at an angle of 45 degrees obliquely, and the transfer of the pressure-sensitive adhesive layer was visually observed. The evaluation is as follows.

◎: There is no stain or foreign matter under the flashlight and the desktop fluorescent lamp, and there is no transfer of the pressure-sensitive layer.

○: There is a small amount of stain under the flashlight, but there is no stain or foreign matter under the desktop fluorescent lamp, and there is no transfer of the pressure-sensitive layer.

×: There are stains under the flashlight and the desktop fluorescent lamp, and the pressure is transferred to the layer.

[Preparation of Polyethylene Terephthalate Resin Film for Primer Treatment]

Add DOW CORNING ^(R) 7499 PSA PRIMER manufactured by Dow Corning Co., Ltd. to a polyethylene terephthalate resin film of 50 μm thickness {Lumirror (registered trademark) manufactured by Toray Co., Ltd. (hereinafter referred to as PET film). Solid content component (22.6 mass%) 100 parts by mass, DOW CORNING ^(R) 7387 CROSSLINKER 1.4 parts by mass of Dow Corning, 500 parts by mass of toluene, and 1,3-divinyl-1,1,3,3 of platinum a tetramethyldioxane complex (the platinum metal in the complex is in an amount of 100 ppm based on the solid content of 7499 described above) and stirred, and then used as a Meyer rod. (No. 3) was applied and hardened in an oven at 120 ° C for 30 seconds.

[Example 1]

Adding dimethyl methoxy oxane-methylvinyl decane copolymer raw rubber with both ends of the molecular chain terminated by dimethyl hydroxy decyloxy group and having at least one vinyl group in one molecule (plasticity = 160, vinyl content = 0.08 mass%) 30 mass% toluene solution 333.3 parts by mass (100 parts by mass based on raw rubber), dynamic viscosity of 33 mm ² /s and molecular chain both ends via trimethyldecyloxy a blocked dimethyloxane-methylhydroquinone copolymer (content of a hydrogen atom bonded to a ruthenium atom = 1.08 mass%) 1.1 parts by mass (relative to the above dimethyl methoxyoxane-methyl group) Vinyl alkane copolymer, vinyl 1 mol in the raw rubber, the hydrogen atom bonded to the ruthenium atom in this component is 4.0 moles, 2-methyl-3-butyn-2-ol 1.0 part by mass and mixed, and further mixed with platinum 1,3-divinyl-1,1,3,3-tetramethyldioxane complex (the platinum metal in the complex is relative to the above dimethyl A toluene solution of a polyfluorene-based pressure-sensitive adhesive was prepared by using a sulfoxane-methylvinylaluminoxane copolymer raw rubber in an amount of 50 ppm by mass.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Embodiment 2]

a dimethyl methoxy oxane-methylvinyl decane copolymer raw rubber 1 having both ends of the molecular chain terminated by dimethyl hydroxy decyloxy group and having at least one vinyl group in one molecule (plasticity degree) =160, vinyl content = 0.08 mass%) 30 mass% toluene solution 170.4 parts by mass (51.1 parts by mass based on raw rubber), and both ends of the molecular chain were terminated with dimethylvinyl alkoxy group and 30% by mass toluene having at least 3 vinyl dimethyl methoxy oxane-methylvinyl fluorene copolymer raw rubber 2 (plasticity = 160, vinyl content = 0.22% by mass) in the molecule 162.9 parts by mass of the solution (48.9 parts by mass in terms of raw rubber) was mixed, and 50 mol% of the end of the molecular chain was prepared to be dimethyl hydroxy alkoxy-terminated dimethyl methoxy oxane-methyl vinyl oxime A 33 mass% toluene solution of the alkane copolymer raw rubber mixture was 333.3 parts by mass (100 parts by mass in terms of raw rubber). Then, to add the movable viscosity of 12.5mm ² / s, and both molecular chain terminals by dimethyl siloxane-terminated silicon bis methylhydrogen silicone alkoxy - methyl hydrogen siloxane copolymer Silicon (Si atom bonded with The content of the hydrogen atom = 0.43 mass%) 5.1 parts by mass (relative to the vinyl group 1 mole in the raw rubber mixture of the above dimethyl methoxy oxane-methylvinyl siloxane), the oxime in the present component 1.0 atomic part of the hydrogen atom bonded to the atom, 1.0 parts by mass of 2-methyl-3-butyn-2-ol, and mixed, and further mixed with platinum 1,3-divinyl-1,1, a 3,3-tetramethyldioxane complex (the platinum metal in the complex is compared with the above dimethyl methoxy oxane-methylvinyl decane copolymer raw rubber mixture, in mass units A toluene solution of a polyfluorene-based pressure-sensitive adhesive was prepared in an amount of 50 ppm.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Example 3]

Adding dimethyl methoxy oxane-methylvinyl decane copolymer raw rubber with both ends of the molecular chain terminated by dimethyl hydroxy decyloxy group and having at least one vinyl group in one molecule (plasticity = 160, vinyl content = 0.08 mass%) 30 mass% toluene solution 333.3 parts by mass (100 parts by mass based on raw rubber), dynamic viscosity of 12.5 mm ² /s and both ends of the molecular chain via dimethylhydroquinone Oxy-terminated dimethyloxane-methylhydroquinone copolymer (content of hydrogen atom bonded to a ruthenium atom = 0.43% by mass) 2.8 parts by mass (relative to the above dimethyloxane- The vinyl 1 methoxy group in the methyl vinyl siloxane copolymer raw rubber, the hydrogen atom bonded to the ruthenium atom in this component is 4.0 moles, 2-methyl-3-butyne-2 - 1.3 parts by mass of an alcohol and mixed, and further mixed with platinum 1,3-divinyl-1,1,3,3-tetramethyldioxane complex (the platinum metal in the complex is relative to the above A toluene solution of a polyfluorene-based pressure-sensitive adhesive was prepared by forming a dimethyl methoxyoxane-methylvinyl siloxane copolymer raw rubber in an amount of 50 ppm by mass.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Example 4]

Adding dimethyl methoxy oxane-methylvinyl decane copolymer raw rubber with both ends of the molecular chain terminated by dimethyl hydroxy decyloxy group and having at least one vinyl group in one molecule (plasticity = 160, vinyl content = 0.08 mass%) 30% by mass toluene solution 266.7 parts by mass (80 parts by mass based on raw rubber), viscosity 385 mPa ‧ and dimethyl vinyl alkoxy group at both ends of the molecular chain Blocked dimethyl polyoxyalkylene (vinyl content = 0.44% by mass) 20 parts by mass, dynamic viscosity of 12.5 mm ² /s and both ends of the molecular chain terminated by dimethylhydroquinoloxy矽 矽 - 甲基 甲基 甲基 甲基 甲基 甲基 甲基 甲基 甲基 甲基 甲基 甲基 甲基 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 5.3 The total of the copolymer raw rubber and the vinyl group in the above dimethyl polyoxyalkylene is 1 mole, and the total of the hydrogen atoms bonded to the ruthenium atom in the present component is 4.0 moles, and 2-methyl-3. - 1.0 part by mass of butyne-2-ol and mixed, and further mixed with platinum 1,3-divinyl-1,1,3,3-tetramethyldioxane complex (in the complex) Platinum The polyxanthene system is prepared in an amount of 50 ppm by mass based on the total of the dimethyl methoxy oxane-methylvinyl siloxane copolymer raw rubber and the dimethyl polyoxy siloxane described above. A toluene solution of the pressure-adhesive agent.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Example 5]

Adding dimethyl methoxy oxane-methylvinyl decane copolymer raw rubber with both ends of the molecular chain terminated by dimethyl hydroxy decyloxy group and having at least one vinyl group in one molecule (plasticity = 160, vinyl content = 0.08 mass%) 30% by mass toluene solution 266.7 parts by mass (80 parts by mass based on raw rubber), viscosity 385 mPa ‧ and dimethyl vinyl alkoxy group at both ends of the molecular chain 20 parts by mass of blocked dimethyl polysiloxane (vinyl content = 0.44% by mass), kinetic viscosity of 33 mm ² /s, and dimethyl hydrazine terminated at both ends of the molecular chain via trimethyldecaneoxy Oxytomane-methylhydroquinone copolymer 1 (content of hydrogen atom bonded to a ruthenium atom = 1.08 mass%) 1.0 part by mass, dynamic viscosity of 12.5 mm ² /s, and dimethyl hydrogen at both ends of the molecular chain a decyloxy-terminated dimethyloxane-methylhydroquinone copolymer 2 (content of a hydrogen atom bonded to a ruthenium atom = 0.43% by mass) 2.6 parts by mass (relative to the above dimethyl oxime) a total of 1 mole of the alkane-methylvinyloxirane copolymer raw rubber and the vinyl group in the above dimethylpolyoxyalkylene, the above dimethyloxane-methylhydroquinone The total of the hydrogen atoms bonded to the ruthenium atom in the alkane copolymers 1 and 2 is 4.0 moles, and 1.0 part by mass of 2-methyl-3-butyn-2-ol is mixed and further mixed with platinum. 1,3-divinyl-1,1,3,3-tetramethyldioxane complex (the platinum metal in the complex relative to the above dimethyloxane-methylvinyloxime) A toluene solution of a polyfluorene-based pressure-sensitive adhesive was prepared by adding a total of the alkane copolymer raw rubber to the above dimethylpolyoxyalkylene in an amount of 50 ppm by mass.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Comparative Example 1]

Adding a dimethyl methoxyoxane-methylvinyl decane copolymer raw rubber with both ends of the molecular chain terminated by dimethylvinyl decyloxy group and having at least one vinyl group in one molecule (plasticity degree) =160, vinyl content = 0.22% by mass) 30% by mass toluene solution 294.6 parts by mass (88.4 parts by mass based on raw rubber), viscosity 385 mPa ‧ and both ends of the molecular chain were subjected to dimethyl vinyl alkane Base-terminated dimethyl polyoxane (vinyl content = 0.44% by mass) 11.6 parts by mass, dynamic viscosity of 33 mm ² /s and dimethyl group terminated at both ends of the molecular chain by trimethyldecaneoxy a decane-methylhydroquinoxane copolymer (content of a hydrogen atom bonded to a ruthenium atom = 1.08 mass%) 3 parts by mass (relative to the above dimethyl methoxy oxane-methylvinyl fluorene copolymer) The total amount of the raw rubber and the vinyl group in the above dimethyl polyoxyalkylene is 1 mole, and the hydrogen atom bonded to the ruthenium atom in the composition is 3.8 moles, and contains (CH ₃ ) ₃ SiO _{1 /2} unit and SiO _4/2 unit and its molar ratio [molar number of (CH ₃ ) ₃ SiO _1/2 unit / mole number of SiO _4/2 unit] is 0.8 methyl polyoxyalkylene resin It 34.9 parts by mass of a 74% by mass xylene solution (25.8 parts by mass based on the resin), 1.4 parts by mass of 2-methyl-3-butyn-2-ol, and mixed, and further mixed with platinum 1,3-divinyl -1,1,3,3-tetramethyldioxane complex (the platinum metal in the complex relative to the above dimethyl methoxyalkane-methylvinyl decane copolymer raw rubber and the above A total of dimethylpolysiloxane (in an amount of 50 ppm by mass) was prepared to prepare a toluene solution of a polyfluorene-based pressure-sensitive adhesive.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Comparative Example 2]

Adding a dimethyl methoxyoxane-methylvinyl decane copolymer raw rubber with both ends of the molecular chain terminated by dimethylvinyl decyloxy group and having at least one vinyl group in one molecule (plasticity degree) =160, vinyl content = 0.22% by mass) 30% by mass toluene solution 333.3 parts by mass (100 parts by mass based on raw rubber), dynamic viscosity of 33 mm ² /s, and both ends of the molecular chain via trimethyldecane oxygen a dimethyl methoxy oxane-methylhydroioxane copolymer (content of a hydrogen atom bonded to a ruthenium atom = 1.08 mass%) of 3 parts by mass (relative to the above dimethyl methoxyoxane-A) Vinyl 1 mole in the raw rubber of the vinyl siloxane copolymer, the hydrogen atom bonded to the ruthenium atom in this component is 4.0 moles, 2-methyl-3-butyne-2- 1.0 part by mass of an alcohol and mixed, and further mixed with platinum 1,3-divinyl-1,1,3,3-tetramethyldioxane complex (the platinum metal in the complex is relative to the above two A toluene solution of a polyfluorene-based pressure-sensitive adhesive was prepared by using a methyl siloxane-methylvinyl siloxane copolymer raw rubber in an amount of 50 ppm by mass.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Comparative Example 3]

100 parts by mass of dimethylpolysiloxane (vinyl content = 0.009% by mass) having a viscosity of 40,700 mPa·s and having both ends of the molecular chain terminated by dimethylvinyl alkoxy group, and an kinetic viscosity of 58.3 mm ² / s and is capped by the silicon-alkoxy trimethyl silicon dimethyl siloxane - methyl hydrogen siloxane copolymer silicone (with the content of hydrogen atoms bonded to the silicon atoms = 1.01 mass%) 1.6 parts by mass (relative The vinyl 1 mole in the above dimethyl polyoxyalkylene, the hydrogen atom bonded to the ruthenium atom in the present component is 5.0 moles, and the 1-ethynyl-1-cyclohexanol 0.2 parts by mass. And mixing, and further mixing platinum 1,3-divinyl-1,1,3,3-tetramethyldioxane complex (the platinum metal in the complex is relative to the above dimethyl polyfluorene) A oxane, in an amount of 50 ppm by mass unit, was used to prepare a toluene solution of a polyfluorene-based pressure-sensitive adhesive.

Then, the solution was applied onto a primer-treated PET film by an applicator, and it was cured at 140 ° C for 2 minutes to prepare an adhesive film having a pressure-sensitive adhesive layer having a thickness of 30 μm. The adhesion of the adhesive film and the results of the transfer test are shown in Table 1.

[Industrial availability]

The polyfluorene-based pressure-sensitive adhesive of the present invention can form a portable computer for covering a mobile phone, a portable music player, a portable personal computer, etc., because it can form a pressure-sensitive adhesive layer with less transfer. The protective film used in the manufacturing process of the cover glass or the touch panel of the display portion is preferable.

1‧‧‧Support

2‧‧‧pressure layer

Claims (7)

A polyfluorene-based pressure-sensitive adhesive comprising at least: at least 25 mol% of the end of the (A) (A1) molecular chain terminated by a hydroxyl group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom and An organopolyoxane having at least one alkenyl group in one molecule, or an organopolyoxy group having a terminal group bonded to a ruthenium atom or a hydrolyzable group bonded to a ruthenium atom at the end of the molecular chain 100 parts by mass of a mixture of an alkane and an (A3) molecular chain end terminated with a triorganosalkoxy group and having at least one alkenyl group in at least one molecule; (B) having at least 3 molecules in one molecule The organopolyoxyalkylene of the hydrogen atom bonded to the ruthenium atom is a total of 1 mole relative to the alkenyl group contained in the component (A), and the hydrogen atom bonded to the ruthenium atom contained in the component is 0.5 mol or more. An amount of 20 moles or less; and (C) a catalyst for hydrogenation reaction (the amount which promotes the hydrogenation reaction of the present composition). The polyoxo-based pressure-sensitive adhesive according to claim 1, wherein the component (A2) is an organopolyoxane having at least one alkenyl group in a molecule. The polyfluorene-based pressure-sensitive adhesive according to claim 1 or 2, wherein the content of the component (A2) is from 5 to 99% by mass based on the component (A). The polyfluorene-based pressure-sensitive adhesive according to claim 1 further contains 5 parts by mass or less of the (D) hydrazine hydrogenation reaction inhibitor with respect to 100 parts by mass of the component (A). The polyoxygen-based pressure-sensitive adhesive according to claim 1 or 4 further contains 10 to 3,000 parts by mass of the (E) organic solvent based on 100 parts by mass of the total of the components (A) and (B). A laminate comprising at least a support and a pressure-sensitive adhesive layer formed by subjecting a polyfluorene-based pressure-sensitive adhesive according to any one of claims 1 to 5 to a hydrogenation reaction. The laminate according to claim 6, wherein the support is a polyethylene terephthalate resin film.