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WO2012108609A1 - Organopolysiloxane, procédé de préparation de celui-ci, et composition de silicone comprenant celui-ci - Google Patents

Organopolysiloxane, procédé de préparation de celui-ci, et composition de silicone comprenant celui-ci Download PDF

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Publication number
WO2012108609A1
WO2012108609A1 PCT/KR2011/008397 KR2011008397W WO2012108609A1 WO 2012108609 A1 WO2012108609 A1 WO 2012108609A1 KR 2011008397 W KR2011008397 W KR 2011008397W WO 2012108609 A1 WO2012108609 A1 WO 2012108609A1
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formula
nhch
organopolysiloxane
compound
alkyl
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Inventor
Seung Kwang Seo
Seung Yeob Choi
Seung Hyun Kang
Jung Mo An
Min Kyoung Park
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KCC Corp
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KCC Corp
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/06—Preparatory processes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/38—Polysiloxanes modified by chemical after-treatment
    • C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
    • C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
    • C08K5/1535—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/15—Heterocyclic compounds having oxygen in the ring
    • C08K5/156—Heterocyclic compounds having oxygen in the ring having two oxygen atoms in the ring
    • C08K5/1565—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
    • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
    • 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
    • C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10H—INORGANIC LIGHT-EMITTING SEMICONDUCTOR DEVICES HAVING POTENTIAL BARRIERS
    • H10H20/00—Individual inorganic light-emitting semiconductor devices having potential barriers, e.g. light-emitting diodes [LED]
    • H10H20/80—Constructional details
    • H10H20/85—Packages
    • H10H20/852—Encapsulations
    • H10H20/854—Encapsulations characterised by their material, e.g. epoxy or silicone resins

Definitions

  • the present invention relates to an organopolysiloxane, a method for preparing the same and a silicone composition comprising the same. More specifically, the present invention provides an organopolysiloxane containing no active amine group and having a specific structure wherein one or more hydroxyl groups are given in its side chain, by which the elasticity and adhesion to a substrate such as a light-emitting diode device can be improved, a method for preparing the same and a silicone composition comprising the same.
  • Epoxy resins have been generally used as sealing materials for light emitting diode (LED) devices.
  • LED light emitting diode
  • silicone resins due to a recently growing need for heat resistance according to the tendency of high luminance and high output of LED, silicone resins have received attention as alternatives thereof.
  • Silicone resins are generally known to have good heat resistance, cold resistance, electric insulation, weatherability, water repellency, transparency and the like, and thus are widely used in various fields such as electric/electronic devices, OA appliances, cars, precision instruments, construction materials and the like.
  • Korean Laid-open Patent Publication No. 10-2007-0049589 discloses a method for improving the adhesion to a gold (Au) substrate by separately adding an alkoxy silane containing acid anhydride group as an adhesion provider in a curable composition for sealing LED devices.
  • Japanese Laid-open Patent Publication No. 2005-161132 discloses a method for preparing a laminated structure with good adhesion strength by using an addition-curable silicone composition containing an adhesion promoter between different two layers, one of which has a hardness of less than 50A whereas the other has a hardness of more than 50A.
  • This publication also discloses as the adhesion promoter, linear or partly branched siloxane resins containing methoxy, glycidoxypropyl or vinyl group.
  • Japanese Patent No. 3344286 discloses a non-solvent type, addition-curable silicone resin composition which has good moldability as compared with solvent type, condensation-curable silicone varnishes, and is remarkably eco-friendly since it does not contain any solvent.
  • the present invention has an object of providing an organopolysiloxane which has good hardness (curing property), light transmittance and refractive index and can provide good elasticity and adhesion by a simple process, and a silicone composition comprising the same.
  • the present invention provides an organopolysiloxane represented by the following Formula 1:
  • each of R 1 , R 2 and R 3 is independently hydrogen, C 1 -C 18 alkyl, C 5 -C 8 cycloalkyl, C 6 -C 10 aryl, C 6 -C 10 arylC 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with 1 to 3 halogens, or C 2 -C 8 alkenyl;
  • each of p, q, r and s is independently an integer of from 1 to 1000.
  • the other aspect of the present invention provides a method for preparing an organopolysiloxane of claim 1, the method comprising reacting a compound of the following Formula 2 with lactone, carbonate, acetic anhydride or succinic acid, or derivative thereof:
  • each of R 1 , R 2 and R 3 is independently hydrogen, C 1 -C 18 alkyl, C 5 -C 8 cycloalkyl, C 6 -C 10 aryl, C 6 -C 10 arylC 1 -C 6 alkyl, C 1 -C 6 alkyl substituted with 1 to 3 halogens, or C 2 -C 8 alkenyl;
  • R 6 is selected from the group consisting of CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 -O-CH 2 CH 2 NHCH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NHCH 2 CH(CH 2 CH 2 NH 2 )CH 2 CH 2 CH 2 NH 2 , CH 2 CH(CH 3 )CH 2 NHCH 2 CH 2 NHCH 3 , CH 2 CH 2 CH 2 NHCH 2 CH 2 NHCH 2 CH 2 NH 2 and CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 ; and
  • each of p, q, r and s is independently an integer of from 1 to 1000.
  • Another aspect of the present invention provides a silicone composition comprising said organopolysiloxane.
  • the present invention can provide silicone materials with good adhesion and elasticity (crack resistance) by a simple process in addition to good hardness (curing property), light transmittance and refractive index, not by separately adding an adhesive additive such as a silane coupling agent but by giving one or more functional groups which show adhesion property to the silicone materials themselves, and thus can be usefully applied as a sealing material, particularly for LED devices.
  • an adhesive additive such as a silane coupling agent but by giving one or more functional groups which show adhesion property to the silicone materials themselves, and thus can be usefully applied as a sealing material, particularly for LED devices.
  • the organopolysiloxane of the present invention is represented by the following Formula 1.
  • each of R 1 , R 2 and R 3 is independently hydrogen; C 1 -C 18 alkyl, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or octadecyl; C 5 -C 8 cycloalkyl, for example, cyclopentyl or cyclohexyl; C 6 -C 10 aryl, for example, phenyl, tolyl, xylyl or naphthyl; C 6 -C 10 arylC 1 -C 6 alkyl, for example, benzyl, phenethyl or 3-phenylpropyl; C 1 -C 6 alkyl substituted with 1 to 3 halogens, for example, 3,3,3-trifluoropropyl or 3-chloropropyl; or C
  • each of p, q, r and s is independently an integer of from 1 to 1000.
  • the present invention relates to reactive organopolysiloxanes useful for luminance improvement, device protection and adhesion in LED devices or the like.
  • the present invention prepares highly refractive organopolysiloxanes, which have a novel structure that is not found in conventional polysiloxanes, by providing reactive curable polysiloxanes with one or more functional groups capable of showing adhesion property.
  • the present invention uses the highly refractive organopolysiloxane prepared as such in a silicone composition used for sealing LED devices or the like.
  • the organopolysiloxane of the present invention contains in its own structure one or more functional groups capable of providing adhesion and elasticity, and thus can reduce the procedures and time for sealing LED devices as compared with conventional methods wherein an adhesion provider is separately added.
  • the organopolysiloxane of the present invention also has an advantage of preventing the crack phenomenon which may cause serious damage to LED devices. Accordingly, an improvement in properties of silicone composition for sealing LED devices and the reduction of cost for manufacturing LED devices can be expected.
  • the organopolysiloxane prepared according to the present invention it is possible to provide a cured product which has an easily controlled refractive index and good hardness, light transmittance and heat resistance, and does not show white turbidity when it is placed in a high temperature/high humidity condition and returned to room temperature.
  • the other aspect of the present invention provides a method for preparing the aforesaid organopolysiloxane of the present invention, the method comprising reacting a compound of the following Formula 2 with lactone, carbonate, acetic anhydride or succinic acid, or derivative thereof.
  • each of R 1 , R 2 and R 3 is independently hydrogen; C 1 -C 18 alkyl, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or octadecyl; C 5 -C 8 cycloalkyl, for example, cyclopentyl or cyclohexyl; C 6 -C 10 aryl, for example, phenyl, tolyl, xylyl or naphthyl; C 6 -C 10 arylC 1 -C 6 alkyl, for example, benzyl, phenethyl or 3-phenylpropyl; C 1 -C 6 alkyl substituted with 1 to 3 halogens, for example, 3,3,3-trifluoropropyl or 3-chloropropyl; or C
  • R 6 is selected from the group consisting of CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 -O-CH 2 CH 2 NHCH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NHCH 2 CH(CH 2 CH 2 NH 2 )CH 2 CH 2 CH 2 NH 2 , CH 2 CH(CH 3 )CH 2 NHCH 2 CH 2 NHCH 3 , CH 2 CH 2 CH 2 NHCH 2 CH 2 NHCH 2 CH 2 NH 2 and CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 ; and
  • each of p, q, r and s is independently an integer of from 1 to 1000.
  • a curable composition for sealing LED devices comprises a combination of reactive organopolysiloxanes and mainly uses platinum catalyst as a curing catalyst.
  • platinum catalyst as a curing catalyst.
  • an active amine group such as R 6 in the above Formula 2 is present in the organopolysiloxane, it acts as a poison to the platinum catalyst and thus the curing does not occur.
  • an organopolysiloxane having -OH group in its side chain can be prepared by using a material such as the following Ex. 2. But in this case, the conversion to the secondary amine group form (-NH-) in the above Ex. 1 occurs and thus the amine activity still exists. Accordingly, it is highly likely that the platinum catalyst would be deactivated during the curing reaction and the curing would fail.
  • a curable organopolysiloxane composition with improved adhesion property can be provided due to the existence of -OH group in the side chain.
  • lactone, carbonate, acetic anhydride or succinic acid, or derivative thereof reacts with R 6 (active amine group-containing substituent) in the above Formula 2
  • the present organopolysiloxane is prepared with various structures according to concrete materials reacting with R 6 .
  • the prepared organopolysiloxane of the present invention has two (2) -OH groups in its side chain end per 1 mol of glycerol carbonate.
  • the present invention gives one or more hydroxyl groups (for example, -(CH 2 )OH)) to the side chain of the compound structure as the following 1) to 9), by which the adhesion property of a silicone material (for example, a silicone material for sealing LED devices) can be improved.
  • a silicone material for example, a silicone material for sealing LED devices
  • the adhesion property of a silicone material for example, a silicone material for sealing LED devices
  • the compound of Formula 2 can be prepared by a method comprising the steps of: (1) condensation-reacting a compound of the following Formula 4 and a compound of the following Formula 5 by using an alkali catalyst; and (2) reacting the product obtained in step (1) with an amine group-containing compound of the following Formula 6 to prepare an organopolysiloxane of Formula 2.
  • each of R 1 , R 2 and R 3 is independently hydrogen; C 1 -C 18 alkyl, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or octadecyl; C 5 -C 8 cycloalkyl, for example, cyclopentyl or cyclohexyl; C 6 -C 10 aryl, for example, phenyl, tolyl, xylyl or naphthyl; C 6 -C 10 arylC 1 -C 6 alkyl, for example, benzyl, phenethyl or 3-phenylpropyl; C 1 -C 6 alkyl substituted with 1 to 3 halogens, for example, 3,3,3-trifluoropropyl or 3-chloropropyl; or C
  • R 6 is selected from the group consisting of CH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 -O-CH 2 CH 2 NHCH 2 CH 2 CH 2 NH 2 , CH 2 CH 2 CH 2 NHCH 2 CH(CH 2 CH 2 NH 2 )CH 2 CH 2 CH 2 NH 2 , CH 2 CH(CH 3 )CH 2 NHCH 2 CH 2 NHCH 3 , CH 2 CH 2 CH 2 NHCH 2 CH 2 NHCH 2 CH 2 NH 2 and CH 2 CH 2 N(CH 2 CH 2 NH 2 ) 2 ; and
  • each of p, q, r and t is independently an integer of from 1 to 1000.
  • an alkali metal hydroxide in the condensation reaction of a compound of the above Formula 4 and a compound of the above Formula 5, an alkali metal hydroxide can be used as the alkali catalyst.
  • Alkali metal hydroxide catalyst is preferably used in an amount of from 1 to 100 ppm (more preferably, from 10 to 50 ppm) based on the weight of reactants in terms of proper maintenance of reaction rate, prevention of color change or white turbidity, minimization of ion (Na + , K + , etc.) content in the final product (concretely, 5 ppm or less) and economy.
  • the reaction of step (1) is conducted at 60 to 200°C (more preferably, 80 to 150°C) for 2 to 3 hours and the reaction of step (2) is conducted at 110 to 200°C for 2 to 4 hours. If the reaction temperature of step (1) is lower than 60°C, the reaction time becomes too long and economic feasibility may become lowered. If the reaction temperature of step (1) is higher than 200°C, the product may be too viscous.
  • Another aspect of the present invention provides a silicone composition comprising the above-explained organopolysiloxane of the present invention.
  • a silicone composition comprising the above-explained organopolysiloxane of the present invention.
  • the silicone composition can be prepared according to any method conventionally used in this field of art.
  • the silicone composition of the present invention is prepared so as to satisfy the properties including proper refractive index, hardness, light transmittance and water absorption rate, which are essentially required in silicone materials used for sealing LED devices or the like.
  • the silicone composition of the present invention preferably has a refractive index of 1.40 or higher (more preferably 1.40 to 1.60) for 589 nm wavelength at 25°C.
  • the silicone composition of the present invention provides a cured product preferably having a durometer (Shore A) hardness of 10 or higher (more preferably 30 to 120) after curing at 150°C for 1 hour.
  • the cured product preferably has a visible light transmittance of 85% or higher (more preferably 85 to 99%) for 400 to 700 nm wavelength.
  • its water absorption rate is preferably 12 g/m 2 or lower after being kept at 38°C for 24 hours.
  • silicone composition of the present invention there is no limitation on the use of the silicone composition of the present invention but it can be particularly applied for sealing LED devices or for optical lenses.
  • organopolysiloxane (Compound of Formula 2) obtained above, glycerol carbonate (Compound of Formula 3) was added in an amount corresponding to 5 times the equivalent amount of amine, polymerization was conducted for 6 hours at 80°C, and excessive glycerol carbonate was removed to obtain colorless, transparent organopolysiloxane (Compound of Formula 1) having a refractive index of 1.52, viscosity of 2600 cP and no active amine content.
  • An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
  • organopolysiloxane (Compound of Formula 2) obtained above, ethylene carbonate (Compound of Formula 3) was added in an amount corresponding to 5 times the equivalent amount of amine, polymerization was conducted for 6 hours at 80°C, and excessive ethylene carbonate was removed to obtain colorless, transparent organopolysiloxane (Compound of Formula 1) having a refractive index of 1.52, viscosity of 1850 cP and no active amine content.
  • An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
  • organopolysiloxane (Compound of Formula 2) obtained above, propylene carbonate (Compound of Formula 3) was added in an amount corresponding to 5 times the equivalent amount of amine, polymerization was conducted for 6 hours at 80°C, and excessive propylene carbonate was removed to obtain colorless, transparent organopolysiloxane (Compound of Formula 1) having a refractive index of 1.52, viscosity of 1900 cP and no active amine content.
  • An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
  • organopolysiloxane (Compound of Formula 2) obtained above, gamma-butyrolactone (Compound of Formula 3) was added in an amount corresponding to 5 times the equivalent amount of amine, polymerization was conducted for 6 hours at 80°C, and excessive gamma-butyrolactone was removed to obtain colorless, transparent organopolysiloxane (Compound of Formula 1) having a refractive index of 1.52, viscosity of 3200 cP and no active amine content.
  • Example 1 The method of Example 1 was stopped when ⁇ Preparation of Compound of Formula 2> was completed, to obtain colorless, transparent organopolysiloxane (Compound of Formula 2) having a refractive index of 1.52, viscosity of 720 cP and active amine content of 0.24% by weight.
  • Compound of Formula 2 having a refractive index of 1.52, viscosity of 720 cP and active amine content of 0.24% by weight.
  • An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
  • organopolysiloxane (Compound of Formula 2) obtained above, glycidol was added in an amount corresponding to 5 times the equivalent amount of amine, the polymerization was conducted for 6 hours at 80°C, and excessive glycidol was removed to obtain colorless, transparent organopolysiloxane having a refractive index of 1.52, viscosity of 1060 cP and active amine content of 0.23% by weight.
  • platinum was added thereto in amount of 10 ppm and mixed uniformly. Curing was conducted at 100°C for 1 hour and further at 150°C for 1 hour to obtain colorless, transparent sealing material for LED devices.
  • the sealing material was cured under pressure at 150°C for 1 hour to obtain a cured silicone body, and it was then processed into a sheet form, for which hardness was measured according to JIS K6253 by using A type or D type durometer.
  • the sealing material was injected into a gap of 0.2 mm between two glass plates and cured at 150°C for 1 hour to obtain a cured silicone sample cell.
  • light transmittance was measured for 450 nm wavelength at 25°C by using an auto-spectrophotometer for any visible light (400 to 700 nm).
  • Refractive index was measured at 25°C for visible light (589 nm) by using an Abbe refractometer.
  • LED packages of polyphthalamide (PPA) were sealed with each of the organopolysiloxanes obtained in Examples 1 to 4 and Comparative Examples 1 to 3 under the same curing condition as explained above.
  • the LED packages sealed with organopolysiloxane were immersed in water at 100°C for 24 hours, and the following two (2) tests were then conducted.
  • the adhesion property was evaluated by representing the penetration area of ink to the contact area of LED package and organopolysiloxane in %.
  • the organopolysiloxanes of the Examples showed light transmittance and a refractive index equivalent to Comparative Example 1 whereas the adhesion property was remarkably better than that of Comparative Example 1. In particular, it can be confirmed that the difference in adhesion property was bigger under the severer condition (100°C ink test).
  • the active amine-containing organopolysiloxanes of Comparative Examples 2 and 3 generated the serious problem that no curing occurred.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
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  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Silicon Polymers (AREA)

Abstract

La présente invention concerne un organopolysiloxane, un procédé de préparation de celui-ci et une composition de silicone comprenant celui-ci. Plus particulièrement, la présente invention concerne un organopolysiloxane ne contenant pas de groupe amine actif et ayant une structure spécifique comprenant un ou plusieurs groupes hydroxyle au niveau de sa chaîne latérale, grâce auxquels peuvent être améliorées l'élasticité et l'adhésion à un substrat tel qu'un dispositif de diode électroluminescente, un procédé de préparation de celui-ci et une composition de silicone comprenant celui-ci.
PCT/KR2011/008397 2011-02-09 2011-11-07 Organopolysiloxane, procédé de préparation de celui-ci, et composition de silicone comprenant celui-ci Ceased WO2012108609A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2011-0011313 2011-02-09
KR1020110011313A KR101213028B1 (ko) 2011-02-09 2011-02-09 오르가노폴리실록산, 그 제조방법 및 이를 포함하는 실리콘 조성물

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WO2012108609A1 true WO2012108609A1 (fr) 2012-08-16

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WO2015025617A1 (fr) 2013-08-19 2015-02-26 住友精化株式会社 Composition de résine de silicone à réticulation par addition, produit de durcissement de résine de silicone réticulée par addition, et corps d'étanchéité d'élément semi-conducteur optique
CN105555873A (zh) * 2013-08-20 2016-05-04 住友精化株式会社 缩合固化型有机硅树脂组合物、缩合固化型有机硅树脂固化物和光半导体元件密封体

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US9181400B2 (en) 2012-11-09 2015-11-10 Sumitomo Seika Chemicals Co., Ltd. Silicone resin composition, cured silicone resin, and sealed optical semiconductor element
WO2014073341A1 (fr) 2012-11-09 2014-05-15 住友精化株式会社 Composition de résine de silicone, résine de silicone durcie et élément semi-conducteur optique scellé
EP3037482A4 (fr) * 2013-08-19 2017-03-29 Sumitomo Seika Chemicals CO. LTD. Composition de résine de silicone à réticulation par addition, produit de durcissement de résine de silicone réticulée par addition, et corps d'étanchéité d'élément semi-conducteur optique
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WO2015025617A1 (fr) 2013-08-19 2015-02-26 住友精化株式会社 Composition de résine de silicone à réticulation par addition, produit de durcissement de résine de silicone réticulée par addition, et corps d'étanchéité d'élément semi-conducteur optique
US9783717B2 (en) 2013-08-19 2017-10-10 Sumitomo Seika Chemicals Co., Ltd. Addition-curable silicone resin composition, addition-curable silicone resin cured product, and sealed optical semiconductor element
TWI623588B (zh) * 2013-08-19 2018-05-11 住友精化股份有限公司 Addition-hardening polyoxynoxy resin composition, addition-hardening polyoxyl resin cured product, and optical semiconductor element sealing body
CN105555873A (zh) * 2013-08-20 2016-05-04 住友精化株式会社 缩合固化型有机硅树脂组合物、缩合固化型有机硅树脂固化物和光半导体元件密封体
EP3037481A4 (fr) * 2013-08-20 2017-04-05 Sumitomo Seika Chemicals CO. LTD. Composition de résine de silicone durcissable par condensation, produit durci en résine de silicone durcissable par condensation, et corps de scellement pour élément semi-conducteur optique
TWI622622B (zh) * 2013-08-20 2018-05-01 住友精化股份有限公司 Condensation hardening type polyoxynoxy resin composition, condensation hardening type polyoxymethylene resin cured product, and optical semiconductor element sealing body
US9963552B2 (en) 2013-08-20 2018-05-08 Sumitomo Seika Chemicals Co., Ltd. Condensation-curable silicone resin composition, condensation-curable silicone resin cured product, and sealed optical semiconductor element
CN105555873B (zh) * 2013-08-20 2018-09-14 住友精化株式会社 缩合固化型有机硅树脂组合物、缩合固化型有机硅树脂固化物和光半导体元件密封体

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