WO2016136245A1 - Organopolysiloxane, son procédé de production et composition de silicone durcissable - Google Patents

Organopolysiloxane, son procédé de production et composition de silicone durcissable Download PDF

Info

Publication number
WO2016136245A1
WO2016136245A1 PCT/JP2016/000961 JP2016000961W WO2016136245A1 WO 2016136245 A1 WO2016136245 A1 WO 2016136245A1 JP 2016000961 W JP2016000961 W JP 2016000961W WO 2016136245 A1 WO2016136245 A1 WO 2016136245A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
organopolysiloxane
carbon atoms
sio
component
Prior art date
Application number
PCT/JP2016/000961
Other languages
English (en)
Japanese (ja)
Inventor
森田　好次
Original Assignee
東レ・ダウコーニング株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 東レ・ダウコーニング株式会社 filed Critical 東レ・ダウコーニング株式会社
Priority to JP2017501938A priority Critical patent/JPWO2016136245A1/ja
Publication of WO2016136245A1 publication Critical patent/WO2016136245A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/14—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms

Definitions

  • the present invention relates to a novel organopolysiloxane having silicon-bonded hydrogen atoms at both ends of a molecular chain, a method for producing the same, and a curable silicone composition containing the organopolysiloxane.
  • a curable silicone composition that is cured by a hydrosilylation reaction to form a cured product having a high refractive index and a high light transmittance is used for semiconductor elements in optical semiconductor devices such as photocouplers, light emitting diodes (LEDs), and solid-state imaging devices. It is used as a protective agent, coating agent, or sealant.
  • Such curable silicone compositions include linear organopolysiloxanes having at least two alkenyl groups and at least one aryl group in one molecule, at least one alkenyl group and at least one in one molecule.
  • an organopolysiloxane having a high degree of polymerization having a silicon atom-bonded hydrogen atom and a silicon atom-bonded aryl group in one molecule In general, it is difficult to prepare an organopolysiloxane having a high degree of polymerization having a silicon atom-bonded hydrogen atom and a silicon atom-bonded aryl group in one molecule.
  • the linear organopolysiloxane having a bonded hydrogen atom has a relatively low degree of polymerization.
  • it in order to improve the physical properties and heat resistance of the cured silicone product obtained by curing, it has at least one silicon atom-bonded aryl group in one molecule and silicon atom bonds at both ends of the molecular chain.
  • Patent Document 2 discloses hydrosilylation reaction of 1,3-divinyl-1,1,3,3-tetramethyldisiloxane and 3,3-diphenyl-1,1,5,5-tetramethyltrisiloxane.
  • the chain-structured organopolysiloxane described in Patent Document 2 is one in which both ends of the molecular chain are blocked with vinyl groups, while the chain-structured organopolysiloxane described in Patent Document 3 is a molecule. It is an alternating copolymer in which the siloxane chain is linked by an alkylene chain, and it is difficult to control the molecular weight during synthesis. The resulting alternating copolymer has low flexibility and does not exhibit sufficient heat resistance. is there.
  • An object of the present invention is to provide a novel organopolysiloxane having silicon-bonded hydrogen atoms at both ends of a molecular chain, and a method for producing the same. Furthermore, another object of the present invention is to provide a curable silicone composition that forms a flexible cured product.
  • the organopolysiloxane of the present invention has the general formula: HR 1 2 SiOSiR 1 2 -R 3 -R 1 2 SiO (R 2 2 SiO) m SiR 1 2 -R 3 -R 1 2 SiOSiR 1 2 H (Wherein R 1 and R 2 are each independently an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, provided that all R (At least 10 mol% of 2 is the aryl group, each R 3 is independently an alkylene group having 2 to 6 carbon atoms, and m is an integer of 5 or more.) It is represented by
  • the curable silicone composition of the present invention is a hydrosilylation reaction-curable silicone composition containing the above organopolysiloxane.
  • R 1 and R 2 are each independently an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, cyclohexyl group, octyl group, nonyl group, decyl group, etc.
  • Examples include alkyl groups; aryl groups such as phenyl, tolyl, xylyl, and naphthyl groups; and aralkyl groups such as benzyl, phenethyl, and phenylpropyl.
  • R 2 is the aryl group, preferably a phenyl group. That is, in the above formula, the general formula: (R 2 2 SiO) m
  • the diorganosiloxane block represented by these contains a diphenylsiloxane unit or a methylphenylsiloxane unit. This is because the refractive index of the organopolysiloxane can be increased.
  • organopolysiloxane of the present invention examples include the following organopolysiloxanes.
  • Me and Ph represent a methyl group and a phenyl group, respectively, and m represents an integer of 5 or more.
  • the (A) component organopolysiloxane has a general formula: R 4 R 1 2 SiO (R 2 2 SiO) m SiR 1 2 R 4 It is represented by
  • R 1 and R 2 are each independently an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms. Specifically, the same groups as described above are exemplified. However, at least 10 mol% of all R 2 is the aryl group, preferably a phenyl group. This is because the refractive index of the resulting organopolysiloxane can be increased.
  • each R 4 is independently an alkenyl group having 2 to 6 carbon atoms.
  • Specific examples include a vinyl group, an allyl group, an isopropenyl group, a butenyl group, an isobutenyl group, a tert-butenyl group, a pentenyl group, an isopentenyl group, and a hexenyl group, and a vinyl group is preferable.
  • m is an integer of 5 or more, and preferably an integer of 10 or more. This is because the curable silicone composition containing the resulting organopolysiloxane can form a flexible cured product.
  • m is preferably an integer of 1,000 or less, or an integer of 500 or less. This is because the reactivity of silicon-bonded hydrogen atoms in the resulting organopolysiloxane is not impaired.
  • Examples of such component (A) include the following organopolysiloxanes.
  • Me, Ph, and Vi represent a methyl group, a phenyl group, and a vinyl group, respectively, and m represents an integer of 5 or more.
  • the organodisiloxane of component (B) has the general formula: HR 1 2 SiOSiR 1 2 H It is represented by
  • each R 1 independently represents an alkyl group having 1 to 12 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, and examples thereof include the same groups as described above.
  • Component (B) is added in an amount such that the silicon-bonded hydrogen atom in this component exceeds 1 mol, preferably 2 mol or more, or 2 with respect to 1 mol of alkenyl group in component (A). It is the amount which becomes .5 mol or more. This is because the more the amount of component (B) added, the more efficiently the organopolysiloxane can be produced. On the other hand, since the unreacted component (B) can be efficiently removed, the amount of component (B) added is 20 moles of silicon-bonded hydrogen atoms in this component with respect to 1 mole of alkenyl group in component (A). The amount is less than or equal to a mole, and preferably less than or equal to 15 moles, less than or equal to 10 moles, or less than or equal to 8 moles.
  • a hydrosilylation reaction catalyst in the production method of the present invention.
  • the catalyst for hydrosilylation reaction is not limited, and examples thereof include platinum-based catalysts, rhodium-based catalysts, and palladium-based catalysts.
  • a platinum-based catalyst is preferable because the hydrosilylation reaction can be significantly accelerated.
  • the platinum-based catalyst include platinum fine powder, chloroplatinic acid, alcohol solution of chloroplatinic acid, platinum-alkenylsiloxane complex, platinum-olefin complex, and platinum-carbonyl complex, particularly platinum-alkenylsiloxane complex. It is preferable.
  • alkenylsiloxane examples include 1,3-divinyl-1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane, Examples include alkenyl siloxanes in which a part of the methyl groups of these alkenyl siloxanes are substituted with groups such as ethyl groups and phenyl groups, and alkenyl siloxanes in which the vinyl groups of these alkenyl siloxanes are substituted with groups such as allyl groups and hexenyl groups. .
  • the addition amount of the catalyst for hydrosilylation reaction is not limited.
  • the catalyst metal is in the range of 0.01 to 1,000 ppm in terms of mass unit with respect to the total amount of component (A) and component (B).
  • the amount is within the range of 0.1 to 500 ppm. This is because when the amount of the hydrosilylation reaction catalyst is at least the lower limit of the above range, the hydrosilylation reaction can be sufficiently promoted. On the other hand, when it is below the upper limit of the above range, the resulting organopolysiloxane can be colored. This is because problems are less likely to occur.
  • reaction conditions in this hydrosilylation reaction are not limited, and the reaction can be promoted by heating.
  • the reaction temperature is preferably the reflux temperature of the solvent. When not used, it is preferably 200 ° C. or lower.
  • the viscosity of the reaction system can be reduced, and water can be dehydrated from the reaction system by azeotropic distillation or the like.
  • the organopolysiloxane thus obtained has silicon-bonded hydrogen atoms at both ends of the molecular chain. Therefore, by adding it to the hydrosilylation reaction-curable silicone composition, it undergoes a hydrosilylation reaction to produce a cured product. A cured product that is incorporated therein, has a small surface tack, and an appropriate elastic modulus can be formed.
  • this organopolysiloxane has an aryl group in the molecule, and thus is suitable as a component of a hydrosilylation reaction-curable silicone composition having a high refractive index.
  • a curable silicone composition for example, (I) an organopolysiloxane having at least two alkenyl groups in one molecule; (II) Organohydrogenpolysiloxane having at least two silicon atom-bonded hydrogen atoms in one molecule ⁇ the silicon atom-bonded hydrogen atom in this component is 0. 1 to 10 mol ⁇ (III) The organopolysiloxane of the present invention (0.1 to 50% by mass with respect to the present composition), and (IV) a catalyst for hydrosilylation reaction (an amount that promotes curing of the present composition) And a hydrosilylation reaction-curable silicone composition comprising at least
  • Component (I) is an organopolysiloxane having at least two alkenyl groups in one molecule.
  • alkenyl group in component (I) the number of carbon atoms such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group and the like is 2 to Twelve alkenyl groups are exemplified, and a vinyl group is preferable.
  • Examples of the group bonded to the silicon atom other than the alkenyl group in the component (I) include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, Alkyl groups having 1 to 12 carbon atoms such as hexyl group, cyclohexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group and dodecyl group; carbon such as phenyl group, tolyl group, xylyl group and naphthyl group An aryl group having 6 to 20 carbon atoms; an aralkyl group having 7 to 20 carbon atoms such as a benzyl group, a phenethyl group, and a phenylpropyl group; a part or all of hydrogen atoms of these
  • the molecular structure of the component (I) is not limited, and examples thereof include a straight chain, a partially branched straight chain, a branched chain, a ring, or a three-dimensional network structure.
  • Component (I) may be a single organopolysiloxane having these molecular structures, or a mixture of two or more organopolysiloxanes having these molecular structures.
  • Component (II) is an organohydrogenpolysiloxane having at least two silicon-bonded hydrogen atoms in one molecule.
  • the group bonded to the silicon atom other than the hydrogen atom in the component includes methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group Alkyl groups having 1 to 12 carbon atoms such as cyclohexyl group, heptyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group and the like; phenyl group, tolyl group, xylyl group, naphthyl group, etc.
  • the silicon atom in the component (II) may have a small amount of a hydroxyl group, an alkoxy group such as a methoxy group, an ethoxy group or the like as long as the object of the present invention is not impaired.
  • the molecular structure of the component (II) is not limited, and examples thereof include linear, partially branched linear, branched, cyclic, or three-dimensional network structure, and preferably partially branched linear , Branched chain, or three-dimensional network structure.
  • component (II) examples include 1,1,3,3-tetramethyldisiloxane, 1,3,5,7-tetramethylcyclotetrasiloxane, tris (dimethylhydrogensiloxy) methylsilane, tris (dimethylhydrogen).
  • the content of the component (II) is such that the silicon-bonded hydrogen atom in this component is 0.1 to 10 mol, preferably 0.1 to 1 mol of the alkenyl group in the component (I).
  • the amount is 5 to 5 mol. This is because if the content of the component (II) is not more than the upper limit of the above range, it is possible to suppress a decrease in the mechanical properties of the resulting cured product, whereas, if not less than the lower limit of the above range, This is because the resulting composition is sufficiently cured.
  • the organopolysiloxane of component (III) is as described above.
  • the content of the component (III) is an amount that falls within the range of 0.1 to 50% by mass, preferably an amount that falls within the range of 5 to 35% by mass with respect to the present composition. This is because when the content of the component (III) is not less than the lower limit of the above range, sufficient flexibility can be imparted to the obtained cured product, and on the other hand, if the content is not more than the upper limit of the above range, the resulting cure can be obtained. This is because the mechanical strength of the object is not lowered.
  • the component (IV) is a hydrosilylation catalyst for promoting the hydrosilylation reaction of the composition.
  • a catalyst for hydrosilylation reaction of the component (IV) is not limited, and examples thereof include platinum-based catalysts, rhodium-based catalysts, and palladium-based catalysts.
  • a platinum-based catalyst is preferable because the hydrosilylation reaction can be significantly accelerated.
  • Examples of the platinum-based catalyst include the same catalysts as described above.
  • the content of the component (IV) is an amount that promotes the curing of the present composition, and preferably the platinum atom in the component (IV) is in the range of 0.01 to 500 ppm by mass with respect to the present composition. Is an amount that falls within the range of 0.01 to 100 ppm, or an amount that falls within the range of 0.1 to 50 ppm. This is because the composition obtained is sufficiently cured when the content of the component (IV) is equal to or higher than the lower limit of the above range, and on the other hand, when the content is equal to or lower than the upper limit of the above range, the resulting cured product is colored. It is because it is suppressed.
  • This composition may contain (E) a hydrosilylation reaction inhibitor as an optional component for extending the pot life at room temperature and improving the storage stability.
  • component (E) include 1-ethynylcyclohexane-1-ol, 2-methyl-3-butyn-2-ol, 3,5-dimethyl-1-hexyn-3-ol, and 2-phenyl- Alkyne alcohols such as 3-butyn-2-ol; Enyne compounds such as 3-methyl-3-penten-1-yne and 3,5-dimethyl-3-hexen-1-yne; 1,3,5,7 A methyl alkenyl siloxane oligomer such as tetramethyl-1,3,5,7-tetravinylcyclotetrasiloxane and 1,3,5,7-tetramethyl-1,3,5,7-tetrahexenylcyclotetrasiloxane; Alkyneoxysilanes such as dimethylbis (1,1-dimethylbutyneoxy) si
  • the group other than the alkoxy group bonded to the silicon atom of the organosilicon compound includes halogen-substituted or unsubstituted monovalent hydrocarbon groups such as alkyl groups, alkenyl groups, aryl groups, aralkyl groups, and halogenated alkyl groups.
  • Glycidoxyalkyl groups such as 3-glycidoxypropyl group and 4-glycidoxybutyl group; 2- (3,4-epoxycyclohexyl) ethyl group and 3- (3,4-epoxycyclohexyl) propyl
  • Examples include an epoxycyclohexylalkyl group such as a group; an epoxyalkyl group such as a 4-epoxybutyl group and an 8-epoxyoctyl group; a 3-methacryloxypropyl group; an isocyanate group; an isocyanurate group; and a hydrogen atom.
  • one or more inorganic fillers selected from silica, glass, alumina and the like as other optional components silicone rubber powder; Resin powder such as silicone resin and polymethacrylate resin; one or more components selected from heat-resistant agents, dyes, pigments, flame retardants, surfactants, solvents and the like may be contained.
  • the organopolysiloxane of the present invention will be described in detail with reference to examples.
  • the viscosity in an Example is a value in 25 degreeC.
  • Me, Ph, Vi, and Ep represent a methyl group, a phenyl group, a vinyl group, and a 3-glycidoxypropyl group, respectively.
  • Example 1 In a reaction vessel, 199.97 g of toluene, formula: ViMe 2 SiO (PhMeSiO) 20 SiMe 2 Vi 167.51 g of a diorganopolysiloxane represented by the following formula (refractive index 1.5438, viscosity 2,625 mPa ⁇ s, mass average molecular weight 4,042), and the formula: HMe 2 SiOSiMe 2 H 15.00 g of disiloxane represented by the formula (in which 3 mol of silicon-bonded hydrogen atoms in this component is 3 mol with respect to 1 mol of vinyl group in the diorganopolysiloxane) is azeotroped at 106 ° C. After dehydration, it was cooled to room temperature.
  • 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex of platinum (the platinum metal in this complex is expressed in mass units with respect to the total amount of the diorganopolysiloxane and the disiloxane). 5 ppm) was added, and the mixture was reacted at a toluene reflux temperature of 111 ° C. to 112 ° C. for 3 hours. Then, after cooling to room temperature and mixing 7.4g of activated carbon, it filtered with the glass filter. Toluene and unreacted disiloxane were distilled off from the filtrate by heating under reduced pressure at 4 mmHg and 100 ° C.
  • This liquid has the formula: HMe 2 SiOSiMe 2 —C 2 H 4 —Me 2 SiO (PhMeSiO) 20 SiMe 2 —C 2 H 4 —Me 2 SiOSiMe 2 H It was found that the organopolysiloxane represented by
  • Example 2 In a reaction vessel, 172.91 g of toluene, general formula: ViMe 2 SiO (PhMeSiO) n SiMe 2 Vi (In the formula, n is about 100.) Diorganopolysiloxane (mass average molecular weight 15,800, refractive index 1.5512, viscosity 41,250 mPa ⁇ s) 124.72 g, and formula: HMe 2 SiOSiMe 2 H After adding 2.50 g of disiloxane represented by the following formula (amount in which 4 moles of silicon-bonded hydrogen atoms in this component are 4 moles per mole of vinyl groups in the diorganopolysiloxane): And cooled to room temperature.
  • 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex of platinum (the platinum metal in this complex is expressed in mass units with respect to the total amount of the diorganopolysiloxane and the disiloxane). 5 ppm) was added, and the reaction was carried out at a toluene reflux temperature of 107 ° C. to 111 ° C. for 2.2 hours. Thereafter, the mixture was cooled to room temperature, mixed with 8.1 g of activated carbon, and filtered through a glass filter. Toluene and unreacted disiloxane were distilled off from the filtrate by heating under reduced pressure at 4 mmHg and 119 ° C.
  • This liquid has the general formula: HMe 2 SiOSiMe 2 —C 2 H 4 —Me 2 SiO (PhMeSiO) n SiMe 2 —C 2 H 4 —Me 2 SiOSiMe 2 H (In the formula, n is about 100.) It was found that the organopolysiloxane represented by
  • Example 3 In a reaction vessel, 172.91 g of toluene, general formula: ViMe 2 SiO (PhMeSiO) m SiMe 2 Vi (Where m is about 8) Diorganopolysiloxane (mass average molecular weight 1,250, refractive index 1.565, viscosity 1,000 mPa ⁇ s) 163.03 g, and formula: HMe 2 SiOSiMe 2 H 49.9 g of disiloxane represented by the formula (in which the amount of silicon-bonded hydrogen atoms in this component is 2.6 mol with respect to 1 mol of vinyl group in the diorganopolysiloxane) is added, and azeotropic dehydration is performed. And then cooled to room temperature.
  • 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex of platinum (the platinum metal in this complex is expressed in mass units with respect to the total amount of the diorganopolysiloxane and the disiloxane). 5 ppm) was added, and the mixture was reacted at a toluene reflux temperature of 100 ° C. to 120 ° C. for 2.5 hours. Thereafter, the mixture was cooled to room temperature, mixed with 13.3 g of activated carbon, and then filtered through a glass filter. Toluene and unreacted disiloxane were distilled off from the filtrate by heating under reduced pressure at 6 mmHg and 100 ° C.
  • This liquid has the general formula: HMe 2 SiOSiMe 2 —C 2 H 4 —Me 2 SiO (PhMeSiO) m SiMe 2 —C 2 H 4 —Me 2 SiOSiMe 2 H (Where m is about 8) It was found that the organopolysiloxane represented by
  • Example 4 In a reaction vessel, 124.89 g of toluene, formula: ViMePhSiO (Ph 2 SiO) 13 (Me 2 SiO) 19 SiMePhVi 61.07 g of a liquid diorganopolysiloxane that is viscous at room temperature (mass average molecular weight 5,100, refractive index 1.5823), and HMe 2 SiOSiMe 2 H After adding 8.81 g of disiloxane represented by the formula (amount of silicon-bonded hydrogen atoms in this component to 7 mol with respect to 1 mol of vinyl groups in the diorganopolysiloxane), And cooled to room temperature.
  • toluene formula: ViMePhSiO (Ph 2 SiO) 13 (Me 2 SiO) 19 SiMePhVi 61.07 g of a liquid diorganopolysiloxane that is viscous at room temperature (mass average molecular weight 5,100
  • 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex of platinum (the platinum metal in this complex is expressed in mass units with respect to the total amount of the diorganopolysiloxane and the disiloxane). 5 ppm) was added, and the mixture was reacted at a toluene reflux temperature of 110 ° C. to 111 ° C. for 3 hours. Thereafter, the mixture was cooled to room temperature, mixed with 10.5 g of activated carbon, and filtered through a glass filter. Toluene and unreacted disiloxane were distilled off from the filtrate by heating under reduced pressure at 63 mmHg and 99 ° C.
  • This liquid has the formula: HMe 2 SiOSiMe 2 —C 2 H 4 —MePhSiO (Ph 2 SiO) 13 (Me 2 SiO) 19 SiMePh—C 2 H 4 —Me 2 SiOSiMe 2 H It was the organopolysiloxane represented by these.
  • platinum 1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex (the platinum metal in this complex is the above-mentioned vinyl group-containing diorganopolysiloxane and the above silicon-bonded hydrogen atom-containing diorgano
  • the amount of 5 ppm in terms of mass unit with respect to the total amount of polysiloxane) was added, and the color was slightly brown due to heat generation. This was heated in a 150 ° C. oven for 1 hour and then cooled to room temperature.
  • a slightly brown transparent liquid having a refractive index of 1.5311, a viscosity of 10,400 mPa ⁇ s, and a weight average molecular weight of 8,120 was obtained.
  • This liquid has the formula: HMe 2 SiOPh 2 SiOSiMe 2- [C 2 H 4 -Me 2 SiOPh 2 SiOSiMe 2 -C 2 H 4 -Me 2 SiOPh 2 SiOSiMe 2- ] m -C 2 H 4 -Me 2 SiOPh 2 SiOSiMe 2 -C 2 H 4- Me 2 SiOPh 2 SiOSiMe 2 H (In the formula, m is 8.) It was found that the organopolysiloxane represented by
  • This curable silicone composition was cured into a plate having a thickness of 1 mm, a length of 20 mm, and a length of 10 mm, and the obtained cured product was measured at an interval of 15 mm using an ARES viscoelasticity measuring apparatus (RDA700 manufactured by Reometric Scientific).
  • the storage elastic modulus of the storage elastic modulus at room temperature was measured under the conditions of a twist of 0.5% and a frequency of 1 Hz.
  • the storage elastic modulus was 350 MPa.
  • Example 5 A curable silicone composition was prepared by blending 20 parts by mass of the organopolysiloxane prepared in Example 1 with 80 parts by mass of the curable silicone composition prepared in Reference Example 1.
  • the cured product obtained by curing this curable silicone composition had a storage elastic modulus of 3 MPa, and the surface of the cured product was not sticky.
  • the organopolysiloxane of the present invention has silicon-bonded hydrogen atoms at both ends of the molecular chain, it can be used as a component of the hydrosilylation reaction-curable silicone composition. Since such a curable silicone composition can form a flexible cured product, it can be used as an adhesive for electric and electronic, a potting agent, a protective coating agent, and an underfill agent. It is suitable as an element adhesive, potting agent, protective coating agent, and underfill agent.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Silicon Polymers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

La présente invention concerne un nouvel organopolysiloxane ayant un atome d'hydrogène lié à un atome de silicium au niveau des deux extrémités de la chaîne moléculaire, et représenté par la formule générale : HR1 2SiOSiR1 2-R3-R1 2SiO(R2 2SiO)mSiR1 2-R2-R1 2SiOSiR1 2H. (Dans la formule, R1 et R2 représentent chacun indépendamment un groupe alkyle en C1-12, un groupe aryle en C6-20, ou un groupe aralkyle en C7-20, au moins 10 % en moles de tous les R2 étant ledit groupe aryle ; les R3 représentent chacun indépendamment un groupe alkylène en C2-6 ; et m est un nombre entier de 5 ou plus.
PCT/JP2016/000961 2015-02-27 2016-02-23 Organopolysiloxane, son procédé de production et composition de silicone durcissable WO2016136245A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2017501938A JPWO2016136245A1 (ja) 2015-02-27 2016-02-23 オルガノポリシロキサン、その製造方法、および硬化性シリコーン組成物

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015-039352 2015-02-27
JP2015039352 2015-02-27

Publications (1)

Publication Number Publication Date
WO2016136245A1 true WO2016136245A1 (fr) 2016-09-01

Family

ID=56788170

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2016/000961 WO2016136245A1 (fr) 2015-02-27 2016-02-23 Organopolysiloxane, son procédé de production et composition de silicone durcissable

Country Status (3)

Country Link
JP (1) JPWO2016136245A1 (fr)
TW (1) TWI688588B (fr)
WO (1) WO2016136245A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2019078046A1 (fr) * 2017-10-20 2019-04-25 東レ・ダウコーニング株式会社 Composition de silicone durcissable et dispositif optique à semi-conducteur
JP2020513447A (ja) * 2016-12-15 2020-05-14 ダウ シリコーンズ コーポレーション 縮合硬化性導電性シリコーン接着剤組成物
JP2021516709A (ja) * 2018-03-19 2021-07-08 ダウ シリコーンズ コーポレーション ポリオレフィン−ポリジオルガノシロキサンブロックコポリマーおよびその合成のための加水分解反応方法
JP7471111B2 (ja) 2020-03-06 2024-04-19 モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 密着剤パッケージ

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0782379A (ja) * 1993-07-21 1995-03-28 Toray Dow Corning Silicone Co Ltd 有機ケイ素重合体の製造方法
JPH07166134A (ja) * 1993-10-22 1995-06-27 Toray Dow Corning Silicone Co Ltd 剥離性硬化皮膜形成用シリコーン組成物
JP2002338692A (ja) * 2001-05-18 2002-11-27 Shin Etsu Chem Co Ltd メチルフェニルポリシロキサンジオール及びその製造方法、並びに液状放射線硬化型樹脂組成物、光ファイバ用被覆組成物及び光ファイバ
WO2012046863A1 (fr) * 2010-10-08 2012-04-12 キヤノン株式会社 Élément de charge, cartouche de traitement et dispositif électrophotographique
JP2012140617A (ja) * 2010-12-31 2012-07-26 Eternal Chemical Co Ltd 硬化性オルガノポリシロキサン組成物及びその製造方法
JP2013056981A (ja) * 2011-09-07 2013-03-28 Daicel Corp ラダー型シルセスキオキサン及びその製造方法、並びに、硬化性樹脂組成物及びその硬化物
US20140231862A1 (en) * 2010-12-31 2014-08-21 Eternal Chemical Co., Ltd. Curable composition and method for manufacturing the same
US20140231861A1 (en) * 2010-12-31 2014-08-21 Eternal Chemical Co., Ltd. Curable composition and method for manufacturing the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5640945B2 (ja) * 2011-10-11 2014-12-17 信越化学工業株式会社 硬化性オルガノポリシロキサン組成物及び半導体装置

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0782379A (ja) * 1993-07-21 1995-03-28 Toray Dow Corning Silicone Co Ltd 有機ケイ素重合体の製造方法
JPH07166134A (ja) * 1993-10-22 1995-06-27 Toray Dow Corning Silicone Co Ltd 剥離性硬化皮膜形成用シリコーン組成物
JP2002338692A (ja) * 2001-05-18 2002-11-27 Shin Etsu Chem Co Ltd メチルフェニルポリシロキサンジオール及びその製造方法、並びに液状放射線硬化型樹脂組成物、光ファイバ用被覆組成物及び光ファイバ
WO2012046863A1 (fr) * 2010-10-08 2012-04-12 キヤノン株式会社 Élément de charge, cartouche de traitement et dispositif électrophotographique
JP2012140617A (ja) * 2010-12-31 2012-07-26 Eternal Chemical Co Ltd 硬化性オルガノポリシロキサン組成物及びその製造方法
US20140231862A1 (en) * 2010-12-31 2014-08-21 Eternal Chemical Co., Ltd. Curable composition and method for manufacturing the same
US20140231861A1 (en) * 2010-12-31 2014-08-21 Eternal Chemical Co., Ltd. Curable composition and method for manufacturing the same
JP2013056981A (ja) * 2011-09-07 2013-03-28 Daicel Corp ラダー型シルセスキオキサン及びその製造方法、並びに、硬化性樹脂組成物及びその硬化物

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020513447A (ja) * 2016-12-15 2020-05-14 ダウ シリコーンズ コーポレーション 縮合硬化性導電性シリコーン接着剤組成物
US11041101B2 (en) 2016-12-15 2021-06-22 Dow Silicones Corporation Condensation-curable electrically conductive silicone adhesive composition
WO2019078046A1 (fr) * 2017-10-20 2019-04-25 東レ・ダウコーニング株式会社 Composition de silicone durcissable et dispositif optique à semi-conducteur
CN111225956A (zh) * 2017-10-20 2020-06-02 杜邦东丽特殊材料株式会社 可固化硅酮组合物及光学半导体装置
JPWO2019078046A1 (ja) * 2017-10-20 2021-03-04 デュポン・東レ・スペシャルティ・マテリアル株式会社 硬化性シリコーン組成物及び光半導体装置
JP2021516709A (ja) * 2018-03-19 2021-07-08 ダウ シリコーンズ コーポレーション ポリオレフィン−ポリジオルガノシロキサンブロックコポリマーおよびその合成のための加水分解反応方法
JP7378411B2 (ja) 2018-03-19 2023-11-13 ダウ シリコーンズ コーポレーション ポリオレフィン－ポリジオルガノシロキサンブロックコポリマーおよびその合成のための加水分解反応方法
JP7471111B2 (ja) 2020-03-06 2024-04-19 モメンティブ・パフォーマンス・マテリアルズ・ジャパン合同会社 密着剤パッケージ

Also Published As

Publication number Publication date
JPWO2016136245A1 (ja) 2017-11-30
TW201641541A (zh) 2016-12-01
TWI688588B (zh) 2020-03-21

Similar Documents

Publication Publication Date Title
US8389650B2 (en) Curable polyorganosiloxane composition
JP5972511B2 (ja) 硬化性オルガノポリシロキサン組成物およびその硬化物
JP5603837B2 (ja) 付加硬化型シリコーン組成物及び光学素子
JP6965346B2 (ja) ダイボンディング用硬化性シリコーン組成物
KR20140043744A (ko) 가교결합성 실리콘 조성물 및 그의 가교결합 생성물
JP6741678B2 (ja) オルガノポリシロキサン、その製造方法、および硬化性シリコーン組成物
WO2016136245A1 (fr) Organopolysiloxane, son procédé de production et composition de silicone durcissable
EP2271700B1 (fr) Organopolysiloxane et son procédé de fabrication, composition de silicone polymérisable et son produit polymérisé
WO2015194159A1 (fr) Organopolysiloxane et son procédé de production
US8674037B2 (en) Silicon-containing polymer, method of manufacturing thereof, and curable polymer composition
JP5913537B2 (ja) 硬化性オルガノポリシロキサン組成物の製造方法
TWI834781B (zh) 可固化聚矽氧組成物及其固化產物
TW202028361A (zh) 可固化聚矽氧組成物及其固化產物

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16754995

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2017501938

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16754995

Country of ref document: EP

Kind code of ref document: A1