WO2012108609A1 - Organopolysiloxane, method for preparing the same, and silicone composition comprising the same - Google Patents
Organopolysiloxane, method for preparing the same, and silicone composition comprising the same Download PDFInfo
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- 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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- organopolysiloxane
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- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 97
- 238000000034 method Methods 0.000 title claims abstract description 33
- 239000000203 mixture Substances 0.000 title claims abstract description 29
- 125000003277 amino group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 52
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- 238000007789 sealing Methods 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 11
- 238000002834 transmittance Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 6
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 6
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 239000000758 substrate Substances 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 description 14
- -1 alkoxy silane Chemical compound 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 238000006116 polymerization reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000003566 sealing material Substances 0.000 description 6
- 229920002050 silicone resin Polymers 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- JFMGYULNQJPJCY-UHFFFAOYSA-N 4-(hydroxymethyl)-1,3-dioxolan-2-one Chemical compound OCC1COC(=O)O1 JFMGYULNQJPJCY-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003822 epoxy resin Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006038 hexenyl group Chemical group 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 230000035515 penetration Effects 0.000 description 3
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- 125000005023 xylyl group Chemical group 0.000 description 3
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004954 Polyphthalamide Substances 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002318 adhesion promoter Substances 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920006375 polyphtalamide Polymers 0.000 description 2
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 0 C*=C[C@]1([C+])*(*)*=*(C)C1 Chemical compound C*=C[C@]1([C+])*(*)*=*(C)C1 0.000 description 1
- 125000004018 acid anhydride group Chemical group 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000004035 construction material Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
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
- C08G77/04—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
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
- H01L33/48—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof characterised by the semiconductor body packages
- H01L33/52—Encapsulations
- H01L33/56—Materials, e.g. epoxy or silicone resin
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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Abstract
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.
Description
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. However, 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.
However, since the adhesion property of silicone resins is relatively inferior to that of epoxy resins, the direct replacement of epoxy resins with silicone resins may cause problems regarding the adhesion to a substrate.
For this reason, 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.
In addition, 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.
Meanwhile, 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.
However, the conventional prior arts including the above publications provide the side chains of the LED-sealing silicone resins with substituents such as phenyl, methyl, vinyl, etc. and use separate additives such as a silane coupling agent to improve the adhesion. In general, along with the main material such as the following 1) to 9), various additives including curing agent and adhesion provider are further added, and thus the process for manufacturing LED packages is very complex and difficult.
1) ViMe2SiO(MePhSiO)nSiMe2Vi
2) ViMe2SiO(MePhSi)m(MeViSiO)nSiMe2Vi
3) ViMe2SiO(MePhSiO)m(MeViSiO)nSiMe3
4) Me3SiO(MePhSiO)m(MeViSiO)nSiMe3
5) HMe2SiO(MePhSiO)nSiMe2H
6) HMe2SiO(MePhSiO)m(MeHSiO)nSiMe2H
7) HMe2SiO(MePhSiO)m(MeHSiO)nSiMe3
8) Me3SiO(MePhSiO)m(MeViSiO)nSiMe3
9) Me3SiO(MePhSiO)m(MeHSiO)nSiMe3
(Vi, Me and Ph represent vinyl, methyl and phenyl, respectively)
Therefore, it is required to develop a method capable of improving the adhesion of silicone materials to substrates through a simple process while maintaining essential properties such as hardness, light transmittance, refractive property, etc. particularly in silicone materials for sealing LED devices.
[PRIOR ART PUBLICATIONS]
<PATENT PUBLICATIONS>
Korean Laid-open Patent Publication No. 10-2007-0049589
Japanese Laid-open Patent Publication No. 2005-161132
Japanese Patent No. 3344286
To resolve the problems of prior arts as explained above, 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.
To achieve the object as explained above, the present invention provides an organopolysiloxane represented by the following Formula 1:
[Formula 1]
wherein in Formula 1,
each of R1, R2 and R3 is independently hydrogen, C1-C18alkyl, C5-C8cycloalkyl, C6-C10aryl, C6-C10arylC1-C6alkyl, C1-C6alkyl substituted with 1 to 3 halogens, or C2-C8alkenyl;
R7 is -R8-N(H)-R9 where R8 is C1-C10alkylene and R9 is -C(=O)-O-R10 or -C(=O)-R10 where R10 is C1-C4alkyl having at least one hydroxyl group [e.g., -(CH2)nOH where n is 1 to 4, or -CH2CH(CH2OH)2]; and
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:
[Formula 2]
wherein in Formula 2,
each of R1, R2 and R3 is independently hydrogen, C1-C18alkyl, C5-C8cycloalkyl, C6-C10aryl, C6-C10arylC1-C6alkyl, C1-C6alkyl substituted with 1 to 3 halogens, or C2-C8alkenyl;
R6 is selected from the group consisting of CH2CH2CH2NH2, CH2CH2-O-CH2CH2NHCH2CH2CH2NH2, CH2CH2CH2NHCH2CH(CH2CH2NH2)CH2CH2CH2NH2, CH2CH(CH3)CH2NHCH2CH2NHCH3, CH2CH2CH2NHCH2CH2NHCH2CH2NH2 and CH2CH2N(CH2CH2NH2)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.
The present invention is explained in detail below.
Organopolysiloxane
The organopolysiloxane of the present invention is represented by the following Formula 1.
[Formula 1]
In the above Formula 1,
each of R1, R2 and R3 is independently hydrogen; C1-C18alkyl, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or octadecyl; C5-C8cycloalkyl, for example, cyclopentyl or cyclohexyl; C6-C10aryl, for example, phenyl, tolyl, xylyl or naphthyl; C6-C10arylC1-C6alkyl, for example, benzyl, phenethyl or 3-phenylpropyl; C1-C6alkyl substituted with 1 to 3 halogens, for example, 3,3,3-trifluoropropyl or 3-chloropropyl; or C2-C8alkenyl, for example, vinyl, allyl, butenyl, pentenyl or hexenyl;
R7 is -R8-N(H)-R9 where R8 is C1-C10alkylene and R9 is -C(=O)-O-R10 or -C(=O)-R10 where R10 is C1-C4alkyl having at least one hydroxyl group [e.g., -(CH2)nOH where n is 1 to 4, or -CH2CH(CH2OH)2]; and
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. Concretely, if the organopolysiloxane prepared according to the present invention is used, 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.
Preparation of organopolysiloxane
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.
[Formula 2]
In the above Formula 2,
each of R1, R2 and R3 is independently hydrogen; C1-C18alkyl, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or octadecyl; C5-C8cycloalkyl, for example, cyclopentyl or cyclohexyl; C6-C10aryl, for example, phenyl, tolyl, xylyl or naphthyl; C6-C10arylC1-C6alkyl, for example, benzyl, phenethyl or 3-phenylpropyl; C1-C6alkyl substituted with 1 to 3 halogens, for example, 3,3,3-trifluoropropyl or 3-chloropropyl; or C2-C8alkenyl, for example, vinyl, allyl, butenyl, pentenyl or hexenyl;
R6 is selected from the group consisting of CH2CH2CH2NH2, CH2CH2-O-CH2CH2NHCH2CH2CH2NH2, CH2CH2CH2NHCH2CH(CH2CH2NH2)CH2CH2CH2NH2, CH2CH(CH3)CH2NHCH2CH2NHCH3, CH2CH2CH2NHCH2CH2NHCH2CH2NH2 and CH2CH2N(CH2CH2NH2)2; and
each of p, q, r and s is independently an integer of from 1 to 1000.
In general, a curable composition for sealing LED devices comprises a combination of reactive organopolysiloxanes and mainly uses platinum catalyst as a curing catalyst. However, if an active amine group (see Ex. 1 below) such as R6 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.
(Ex. 1)
Primary amine group: -NH2
Secondary amine group: -N(H)-R (R is generally C1-C10alkyl having at least one hydroxyl group)
Meanwhile, 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.
(Ex. 2)
In the present invention, all amine groups existing in an organopolysiloxane structure such as the above Formula 2 are converted to -N-C(=O)-R or -N-C(=O)-O-R structure, by which it is possible to prevent the curing failure and impart good elasticity. Furthermore, a curable organopolysiloxane composition with improved adhesion property can be provided due to the existence of -OH group in the side chain. Concretely, lactone, carbonate, acetic anhydride or succinic acid, or derivative thereof reacts with R6 (active amine group-containing substituent) in the above Formula 2, and the present organopolysiloxane is prepared with various structures according to concrete materials reacting with R6. For example, if glycerol carbonate among carbonate compounds is used, the prepared organopolysiloxane of the present invention has two (2) -OH groups in its side chain end per 1 mol of glycerol carbonate.
In an embodiment, the present invention gives one or more hydroxyl groups (for example, -(CH2)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. In addition, because of the incorporation of -N-C(=O)-O structure or the like, after the curing the elasticity of silicone material can be improved and the brittleness can be reduced, by which the cracking of the cured product can be prevented.
1) ViMe2SiO(MePhSiO)nSiMe2Vi
2) ViMe2SiO(MePhSi)m(MeViSiO)nSiMe2Vi
3) ViMe2SiO(MePhSiO)m(MeViSiO)nSiMe3
4) Me3SiO(MePhSiO)m(MeViSiO)nSiMe3
5) HMe2SiO(MePhSiO)nSiMe2H
6) HMe2SiO(MePhSiO)m(MeHSiO)nSiMe2H
7) HMe2SiO(MePhSiO)m(MeHSiO)nSiMe3
8) Me3SiO(MePhSiO)m(MeViSiO)nSiMe3
9) Me3SiO(MePhSiO)m(MeHSiO)nSiMe3
Concretely, as the lactone, carbonate, acetic anhydride or succinic acid, or derivative thereof which reacts with the compound of Formula 2, a compound selected from the following group of Formula 3 can be used.
[Formula 3]
In a preferred embodiment, 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.
[Formula 4]
[Formula 5]
[Formula 6]
In the above Formulas 4 to 6,
each of R1, R2 and R3 is independently hydrogen; C1-C18alkyl, for example, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl or octadecyl; C5-C8cycloalkyl, for example, cyclopentyl or cyclohexyl; C6-C10aryl, for example, phenyl, tolyl, xylyl or naphthyl; C6-C10arylC1-C6alkyl, for example, benzyl, phenethyl or 3-phenylpropyl; C1-C6alkyl substituted with 1 to 3 halogens, for example, 3,3,3-trifluoropropyl or 3-chloropropyl; or C2-C8alkenyl, for example, vinyl, allyl, butenyl, pentenyl or hexenyl;
R6 is selected from the group consisting of CH2CH2CH2NH2, CH2CH2-O-CH2CH2NHCH2CH2CH2NH2, CH2CH2CH2NHCH2CH(CH2CH2NH2)CH2CH2CH2NH2, CH2CH(CH3)CH2NHCH2CH2NHCH3, CH2CH2CH2NHCH2CH2NHCH2CH2NH2 and CH2CH2N(CH2CH2NH2)2; and
each of p, q, r and t is independently an integer of from 1 to 1000.
Concretely, 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.
In a preferred embodiment, the reaction of step (1) is conducted at 60 to 200℃ (more preferably, 80 to 150℃) for 2 to 3 hours and the reaction of step (2) is conducted at 110 to 200℃ for 2 to 4 hours. If the reaction temperature of step (1) is lower than 60℃, the reaction time becomes too long and economic feasibility may become lowered. If the reaction temperature of step (1) is higher than 200℃, the product may be too viscous.
Silicone composition
Another aspect of the present invention provides a silicone composition comprising the above-explained organopolysiloxane of the present invention. There is no particular limitation in the method for preparing the silicone composition for sealing LED devices or the like by using the 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. Concretely, 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℃. 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℃ for 1 hour. Furthermore, the cured product preferably has a visible light transmittance of 85% or higher (more preferably 85 to 99%) for 400 to 700 nm wavelength. In addition, its water absorption rate is preferably 12 g/m2 or lower after being kept at 38℃ for 24 hours.
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.
The present invention is explained in more detail by the following Examples and Comparative Examples. However, they are just intended to facilitate the understanding of the present invention, and the scope of the present invention is not limited by them.
Example 1
<Preparation of Compound of Formula 2>
In a flask, 100 parts by weight of α,ω-hydroxydimethylsilyl-methylphenylpolysiloxane (Compound of Formula 4), 20 parts by weight of α,ω-vinyldimethylsilyl-methylphenylpolysiloxane (Compound of Formula 5) and 0.08 part by weight of aqueous solution of 45% KOH (alkali catalyst) were added, the temperature was elevated to 110℃ under reduced pressure, and polymerization was conducted for 3 hours.
To the product obtained above, 12.3 parts by weight of hydroxyl-ended aminopropylmethylpolysiloxane (Compound of Formula 6), 10 parts by weight of vinylmethyltetracyclosiloxane and 30 parts by weight of dimethyltetracyclosiloxane were added, and polymerization was conducted for 4 hours at 160℃. H3PO4 was added thereto in an amount corresponding to the equivalent amount of KOH and the resulting mixture was stripped at 250℃ and cooled 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.
< Preparation of Compound of Formula 1>
To the 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℃, 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.
Example 2
<Preparation of Compound of Formula 2>
An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
< Preparation of Compound of Formula 1>
To the 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℃, 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.
Example 3
<Preparation of Compound of Formula 2>
An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
< Preparation of Compound of Formula 1>
To the 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℃, 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.
Example 4
<Preparation of Compound of Formula 2>
An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
< Preparation of Compound of Formula 1>
To the 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℃, 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.
Comparative Example 1
In a flask, 100 parts by weight of α,ω-hydroxydimethylsilyl-methylphenylpolysiloxane (Compound of Formula 4), 20 parts by weight of α,ω-vinyldimethylsilyl-methylphenylpolysiloxane (Compound of Formula 5) and 0.08 part by weight of aqueous solution of 45% KOH (alkali catalyst) were added, the temperature was elevated to 110℃ under reduced pressure, and polymerization was conducted for 3 hours.
To the product obtained above, 10 parts by weight of vinylmethyltetracyclosiloxane and 42.3 parts by weight of dimethyltetracyclosiloxane were added, and polymerization was conducted for 4 hours at 160℃. H3PO4 was added thereto in an amount corresponding to the equivalent amount of KOH and the resulting mixture was stripped at 250℃ and cooled to obtain colorless, transparent organopolysiloxane (Compound of Formula 2, except that r = 0) having a refractive index of 1.52 and viscosity of 600 cP.
Comparative Example 2
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.
Comparative Example 3
<Preparation of Compound of Formula 2>
An organopolysiloxane (Compound of Formula 2) was prepared according to the same method as that of Example 1.
< Preparation of Final Organopolysiloxane>
To the 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℃, 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.
Curing Property Evaluation
With each of the final organopolysiloxanes prepared in the Examples and Comparative Examples, methylphenylhydro-organopolysiloxane was mixed with the ratio of H/Vi = 1.5. As a catalyst, platinum was added thereto in amount of 10 ppm and mixed uniformly. Curing was conducted at 100℃ for 1 hour and further at 150℃ for 1 hour to obtain colorless, transparent sealing material for LED devices.
To each of the cured products (sealing materials for LED devices) according to the Examples and Comparative Examples, properties were measured by the following methods, and the results are shown in the following Table 1.
- Hardness
The sealing material was cured under pressure at 150℃ 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.
- Light transmittance
The sealing material was injected into a gap of 0.2 mm between two glass plates and cured at 150℃ for 1 hour to obtain a cured silicone sample cell. With the cured silicone sample, light transmittance was measured for 450 nm wavelength at 25℃ by using an auto-spectrophotometer for any visible light (400 to 700 nm).
- Refractive index
Refractive index was measured at 25℃ for visible light (589 nm) by using an Abbe refractometer.
- Adhesion property (Ink test)
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℃ for 24 hours, and the following two (2) tests were then conducted.
1) Investigation of ink penetration after immersion in ink at 25℃ for 24 hours
2) Investigation of ink penetration after immersion in ink at 100℃ for 2 hours
The adhesion property was evaluated by representing the penetration area of ink to the contact area of LED package and organopolysiloxane in %.
Table 1 
As can be seen from the above Table 1, 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℃ ink test). In addition, the active amine-containing organopolysiloxanes of Comparative Examples 2 and 3 generated the serious problem that no curing occurred.
Claims (10)
- An organopolysiloxane represented by the following Formula 1:[Formula 1]
wherein in Formula 1,each of R1, R2 and R3 is independently hydrogen, C1-C18alkyl, C5-C8cycloalkyl, C6-C10aryl, C6-C10arylC1-C6alkyl, C1-C6alkyl substituted with 1 to 3 halogens, or C2-C8alkenyl;R7 is -R8-N(H)-R9 where R8 is C1-C10alkylene and R9 is -C(=O)-O-R10 or -C(=O)-R10 where R10 is C1-C4alkyl having at least one hydroxyl group; andeach of p, q, r and s is independently an integer of from 1 to 1000. - 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:[Formula 2]
wherein in Formula 2,each of R1, R2 and R3 is independently hydrogen, C1-C18alkyl, C5-C8cycloalkyl, C6-C10aryl, C6-C10arylC1-C6alkyl, C1-C6alkyl substituted with 1 to 3 halogens, or C2-C8alkenyl;R6 is selected from the group consisting of CH2CH2CH2NH2, CH2CH2-O-CH2CH2NHCH2CH2CH2NH2, CH2CH2CH2NHCH2CH(CH2CH2NH2)CH2CH2CH2NH2, CH2CH(CH3)CH2NHCH2CH2NHCH3, CH2CH2CH2NHCH2CH2NHCH2CH2NH2 and CH2CH2N(CH2CH2NH2)2; andeach of p, q, r and s is independently an integer of from 1 to 1000. - The method according to claim 2, wherein the lactone, carbonate, acetic anhydride or succinic acid, or derivative thereof is a compound selected from the following group of Formula 3:[Formula 3]
- The method according to claim 2, wherein the compound of Formula 2 is 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:[Formula 4]
[Formula 5]
[Formula 6]
wherein in Formulas 4 to 6,each of R1, R2 and R3 is independently hydrogen, C1-C18alkyl, C5-C8cycloalkyl, C6-C10aryl, C6-C10arylC1-C6alkyl, C1-C6alkyl substituted with 1 to 3 halogens, or C2-C8alkenyl;R6 is selected from the group consisting of CH2CH2CH2NH2, CH2CH2-O-CH2CH2NHCH2CH2CH2NH2, CH2CH2CH2NHCH2CH(CH2CH2NH2)CH2CH2CH2NH2, CH2CH(CH3)CH2NHCH2CH2NHCH3, CH2CH2CH2NHCH2CH2NHCH2CH2NH2 and CH2CH2N(CH2CH2NH2)2; andeach of p, q, r and t is independently an integer of from 1 to 1000. - The method according to claim 4, wherein the reaction of step (1) is conducted at 60 to 200℃ for 2 to 3 hours and the reaction of step (2) is conducted at 110 to 200℃ for 2 to 4 hours.
- A silicone composition comprising an organopolysiloxane of claim 1.
- The silicone composition according to claim 6, which has a refractive index of 1.40 or higher for 589 nm wavelength at 25℃.
- The silicone composition according to claim 6, which provides a cured product having a durometer (Shore A) hardness of 10 or higher after curing at 150℃ for 1 hour.
- The silicone composition according to claim 6, which provides a cured product having a visible light transmittance of 85% or higher for 400 to 700 nm wavelength.
- The silicone composition according to any one of claims 6 to 9, which is used for sealing light-emitting diode (LED) devices or for optical lenses.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2011-0011313 | 2011-02-09 | ||
| KR1020110011313A KR101213028B1 (en) | 2011-02-09 | 2011-02-09 | Organopolysiloxane, method for preparing the same, and silicon composition comprising the same |
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| WO2012108609A1 true WO2012108609A1 (en) | 2012-08-16 |
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| PCT/KR2011/008397 WO2012108609A1 (en) | 2011-02-09 | 2011-11-07 | Organopolysiloxane, method for preparing the same, and silicone composition comprising the same |
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Cited By (3)
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| WO2014073341A1 (en) | 2012-11-09 | 2014-05-15 | 住友精化株式会社 | Silicone resin composition, cured silicone resin, and sealed optical semiconductor element |
| WO2015025617A1 (en) | 2013-08-19 | 2015-02-26 | 住友精化株式会社 | Addition-cured silicone resin composition, curing product of addition-cured silicone resin, and optical semiconductor element sealing body |
| CN105555873A (en) * | 2013-08-20 | 2016-05-04 | 住友精化株式会社 | Condensation-curable silicone resin composition, cured product of condensation-curable silicone resin, and optical semiconductor element sealing body |
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| US5527935A (en) * | 1993-09-23 | 1996-06-18 | Wacker-Chemie Gmbh | Organopolysiloxanes having bifunctional terminal siloxane units |
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| GB9702234D0 (en) | 1997-02-04 | 1997-03-26 | Dow Corning | Process for stabilising siloxane polymers |
| JP4503271B2 (en) | 2003-11-28 | 2010-07-14 | 東レ・ダウコーニング株式会社 | Method for producing silicone laminate |
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- 2011-02-09 KR KR1020110011313A patent/KR101213028B1/en not_active IP Right Cessation
- 2011-11-07 WO PCT/KR2011/008397 patent/WO2012108609A1/en active Application Filing
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| US4801622A (en) * | 1987-02-03 | 1989-01-31 | Shin-Etsu Chemical Co., Ltd. | Curable and foamable organopolysiloxane composition |
| US5527935A (en) * | 1993-09-23 | 1996-06-18 | Wacker-Chemie Gmbh | Organopolysiloxanes having bifunctional terminal siloxane units |
| US5674963A (en) * | 1994-04-20 | 1997-10-07 | Bayer Aktiengesellschaft | Preparing reaction products from poly (diorganosiloxanes) |
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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 (en) | 2012-11-09 | 2014-05-15 | 住友精化株式会社 | Silicone resin composition, cured silicone resin, and sealed optical semiconductor element |
| 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 |
| WO2015025617A1 (en) | 2013-08-19 | 2015-02-26 | 住友精化株式会社 | Addition-cured silicone resin composition, curing product of addition-cured silicone resin, and optical semiconductor element sealing body |
| CN105492541A (en) * | 2013-08-19 | 2016-04-13 | 住友精化株式会社 | Addition-cured silicone resin composition, curing product of addition-cured silicone resin, and optical semiconductor element sealing body |
| KR20160045754A (en) | 2013-08-19 | 2016-04-27 | 스미또모 세이까 가부시키가이샤 | Addition-cured silicone resin composition, curing product of addition-cured silicone resin, and optical semiconductor element sealing body |
| TWI623588B (en) * | 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 |
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| EP3037481A4 (en) * | 2013-08-20 | 2017-04-05 | Sumitomo Seika Chemicals CO. LTD. | Condensation-curable silicone resin composition, cured product of condensation-curable silicone resin, and optical semiconductor element sealing body |
| TWI622622B (en) * | 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 |
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| CN105555873B (en) * | 2013-08-20 | 2018-09-14 | 住友精化株式会社 | Condensation cured type organosilicon resin composition, condensation cured type silicone cured product and optical semiconductor seal |
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| Publication number | Publication date |
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| KR20120091518A (en) | 2012-08-20 |
| KR101213028B1 (en) | 2012-12-18 |
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