JP2007510772A - より強靱な脂環式エポキシ樹脂 - Google Patents
より強靱な脂環式エポキシ樹脂 Download PDFInfo
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- JP2007510772A JP2007510772A JP2006537988A JP2006537988A JP2007510772A JP 2007510772 A JP2007510772 A JP 2007510772A JP 2006537988 A JP2006537988 A JP 2006537988A JP 2006537988 A JP2006537988 A JP 2006537988A JP 2007510772 A JP2007510772 A JP 2007510772A
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- Prior art keywords
- coating
- resin
- epoxy resin
- reaction
- epoxide
- Prior art date
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- 239000011248 coating agent Substances 0.000 claims abstract description 79
- 238000000034 method Methods 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- -1 alicyclic epoxide ester Chemical class 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims description 52
- 239000000047 product Substances 0.000 claims description 21
- 239000011353 cycloaliphatic epoxy resin Substances 0.000 claims description 10
- 238000009472 formulation Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
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- 239000007795 chemical reaction product Substances 0.000 claims description 6
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- 239000003999 initiator Substances 0.000 claims description 2
- 238000005452 bending Methods 0.000 abstract description 2
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- 0 *C1(C(*)(C(*)(C2)[Mn])N=I)OC1(*)C2(N)N=C Chemical compound *C1(C(*)(C(*)(C2)[Mn])N=I)OC1(*)C2(N)N=C 0.000 description 5
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- PFURGBBHAOXLIO-PHDIDXHHSA-N trans-cyclohexane-1,2-diol Chemical compound O[C@@H]1CCCC[C@H]1O PFURGBBHAOXLIO-PHDIDXHHSA-N 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- SDUZNEIVCAVWSH-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-3,4-dicarboxylic acid Chemical compound C1C(C(O)=O)C(C(=O)O)CC2OC21 SDUZNEIVCAVWSH-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
- 150000004844 dioxiranes Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- ALEAMASTTOYSRW-UHFFFAOYSA-N ethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OCC)CCC2OC21 ALEAMASTTOYSRW-UHFFFAOYSA-N 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- NQUPKCJGWCPODR-UHFFFAOYSA-N hexaneperoxoic acid Chemical compound CCCCCC(=O)OO NQUPKCJGWCPODR-UHFFFAOYSA-N 0.000 description 1
- DOMDHOJBUSKAGM-UHFFFAOYSA-N hexyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical class C1C(C(=O)OCCCCCC)CCC2OC21 DOMDHOJBUSKAGM-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- VRNINGUKUJWZTH-UHFFFAOYSA-L lead(2+);dithiocyanate Chemical compound [Pb+2].[S-]C#N.[S-]C#N VRNINGUKUJWZTH-UHFFFAOYSA-L 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- AZVCGYPLLBEUNV-UHFFFAOYSA-N lithium;ethanolate Chemical compound [Li+].CC[O-] AZVCGYPLLBEUNV-UHFFFAOYSA-N 0.000 description 1
- ZJZXSOKJEJFHCP-UHFFFAOYSA-M lithium;thiocyanate Chemical compound [Li+].[S-]C#N ZJZXSOKJEJFHCP-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- VQAKAOYUEOMWPM-UHFFFAOYSA-N methyl 3-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C)C(C(=O)OC)CC2OC21 VQAKAOYUEOMWPM-UHFFFAOYSA-N 0.000 description 1
- GOURYLUXGBHOJH-UHFFFAOYSA-N methyl 6-methyl-7-oxabicyclo[4.1.0]heptane-3-carboxylate Chemical compound C1C(C(=O)OC)CCC2(C)OC21 GOURYLUXGBHOJH-UHFFFAOYSA-N 0.000 description 1
- MQISPSYWHGSCQH-UHFFFAOYSA-N methyl 6-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC)CCC2OC21C MQISPSYWHGSCQH-UHFFFAOYSA-N 0.000 description 1
- QCGKUFZYSPBMAY-UHFFFAOYSA-N methyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC)CCC2OC21 QCGKUFZYSPBMAY-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- MKNZKCSKEUHUPM-UHFFFAOYSA-N potassium;butan-1-ol Chemical compound [K+].CCCCO MKNZKCSKEUHUPM-UHFFFAOYSA-N 0.000 description 1
- RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
- 235000013324 preserved food Nutrition 0.000 description 1
- HWFXVRAZRNRWHJ-UHFFFAOYSA-N propan-2-yl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC(C)C)CCC2OC21 HWFXVRAZRNRWHJ-UHFFFAOYSA-N 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- CQAPIGCHBWZHKD-UHFFFAOYSA-N propyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OCCC)CCC2OC21 CQAPIGCHBWZHKD-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- JXKPEJDQGNYQSM-UHFFFAOYSA-M sodium propionate Chemical compound [Na+].CCC([O-])=O JXKPEJDQGNYQSM-UHFFFAOYSA-M 0.000 description 1
- 239000004324 sodium propionate Substances 0.000 description 1
- 235000010334 sodium propionate Nutrition 0.000 description 1
- 229960003212 sodium propionate Drugs 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- RCOSUMRTSQULBK-UHFFFAOYSA-N sodium;propan-1-olate Chemical compound [Na+].CCC[O-] RCOSUMRTSQULBK-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- IYFFLHIMMREMAV-UHFFFAOYSA-N tert-butyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC(C)(C)C)CCC2OC21 IYFFLHIMMREMAV-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 229910002007 uranyl nitrate Inorganic materials 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229960000314 zinc acetate Drugs 0.000 description 1
- 235000013904 zinc acetate Nutrition 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 1
- JXNCWJJAQLTWKR-UHFFFAOYSA-N zinc;methanolate Chemical compound [Zn+2].[O-]C.[O-]C JXNCWJJAQLTWKR-UHFFFAOYSA-N 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/681—Metal alcoholates, phenolates or carboxylates
- C08G59/682—Alcoholates
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/24—Di-epoxy compounds carbocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
- Epoxy Compounds (AREA)
- Structures Or Materials For Encapsulating Or Coating Semiconductor Devices Or Solid State Devices (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51687803P | 2003-11-03 | 2003-11-03 | |
| PCT/US2004/029996 WO2005044890A1 (en) | 2003-11-03 | 2004-09-10 | Tougher cycloaliphatic epoxide resins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007510772A true JP2007510772A (ja) | 2007-04-26 |
| JP2007510772A5 JP2007510772A5 (enExample) | 2007-10-25 |
Family
ID=34572899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006537988A Pending JP2007510772A (ja) | 2003-11-03 | 2004-09-10 | より強靱な脂環式エポキシ樹脂 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20070042191A1 (enExample) |
| EP (1) | EP1682599A1 (enExample) |
| JP (1) | JP2007510772A (enExample) |
| KR (1) | KR20060113912A (enExample) |
| CN (1) | CN1875045A (enExample) |
| AR (1) | AR046438A1 (enExample) |
| BR (1) | BRPI0415812A (enExample) |
| TW (1) | TW200523288A (enExample) |
| WO (1) | WO2005044890A1 (enExample) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006241180A (ja) * | 2005-02-28 | 2006-09-14 | Daicel Chem Ind Ltd | 紫外線硬化型缶用塗料組成物、塗装金属板、および塗装金属缶 |
| JP2010241942A (ja) * | 2009-04-03 | 2010-10-28 | Nippon Kayaku Co Ltd | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
| JP2011016880A (ja) * | 2009-07-07 | 2011-01-27 | Nippon Kayaku Co Ltd | 光半導体封止用硬化性樹脂組成物、及びその硬化物 |
| JP2011079794A (ja) * | 2009-10-09 | 2011-04-21 | Nippon Kayaku Co Ltd | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
| WO2011078205A1 (ja) * | 2009-12-24 | 2011-06-30 | 日本化薬株式会社 | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物、並びに光半導体装置 |
| WO2011078322A1 (ja) * | 2009-12-24 | 2011-06-30 | 日本化薬株式会社 | エポキシ樹脂組成物、硬化性樹脂組成物、およびその硬化物 |
| WO2011145733A1 (ja) * | 2010-05-21 | 2011-11-24 | 日本化薬株式会社 | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
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| JP2005330335A (ja) * | 2004-05-18 | 2005-12-02 | Nitto Denko Corp | 光半導体素子封止用エポキシ樹脂組成物およびそれを用いた光半導体装置 |
| US7288607B2 (en) * | 2004-10-12 | 2007-10-30 | E. I. Du Pont De Nemours & Co. | High solids primer composition based on epoxy ring opening curing reaction |
| JP4683933B2 (ja) * | 2005-01-19 | 2011-05-18 | ダイセル化学工業株式会社 | 硬化性樹脂組成物および層間絶縁膜 |
| JP2007039521A (ja) * | 2005-08-02 | 2007-02-15 | Stanley Electric Co Ltd | 熱硬化性樹脂組成物、該組成物を熱硬化してなる透光性硬化物、該硬化物で封止された発光ダイオード |
| JP5319971B2 (ja) * | 2008-06-27 | 2013-10-16 | 昭和電工株式会社 | 脂環式エポキシ基含有エステル化合物の製造方法 |
| BR112012033390A2 (pt) | 2010-06-28 | 2016-11-22 | Dow Global Technologies Llc | composição curável por uv, processo para preparar uma composição de resina de dióxido de divinilareno curável e produto curado |
| US9861452B2 (en) | 2013-08-09 | 2018-01-09 | Dsm Ip Assets B.V. | Low-viscosity liquid radiation curable dental aligner mold resin compositions for additive manufacturing |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5981329A (ja) * | 1982-09-30 | 1984-05-11 | ユニオン、カーバイド、コーポレーシヨン | 硬化し得るエポキシ樹脂含有成形組成物 |
| JPS62230861A (ja) * | 1985-12-19 | 1987-10-09 | ユニオン・カ−バイド・コ−ポレ−シヨン | 光硬化性相似被覆組成物 |
| JPS63261259A (ja) * | 1987-04-06 | 1988-10-27 | チバ−ガイギー アクチエンゲゼルシヤフト | 光構造性塗膜の製造方法 |
| JPH10251375A (ja) * | 1997-03-06 | 1998-09-22 | Ciba Specialty Chem Holding Inc | α−グリコール基含有グリシジル化合物 |
| JP2000159764A (ja) * | 1998-11-24 | 2000-06-13 | Ciba Specialty Chem Holding Inc | ピペラジノン誘導体 |
| JP2001200200A (ja) * | 1999-11-10 | 2001-07-24 | Vantico Ag | 硬化性組成物 |
| JP2002338659A (ja) * | 2001-05-14 | 2002-11-27 | Daicel Chem Ind Ltd | 液状エポキシ樹脂組成物及びその用途 |
| JP2002371073A (ja) * | 2001-06-12 | 2002-12-26 | Asahi Kasei Corp | エポキシ含有脂環式エステルの製法 |
| JP2003176333A (ja) * | 2001-08-23 | 2003-06-24 | General Electric Co <Ge> | エポキシ樹脂組成物、該組成物で封入された固体素子デバイス及び封入方法 |
| JP2003342268A (ja) * | 2002-05-28 | 2003-12-03 | Nippon Kasei Chem Co Ltd | エポキシ基末端(メタ)アクリレートの製造方法 |
| JP2004067947A (ja) * | 2002-08-08 | 2004-03-04 | Nippon Soda Co Ltd | 光触媒層形成用塗布液および光触媒担持構造体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US516878A (en) * | 1894-03-20 | Joseph sachs | ||
| JPS608246B2 (ja) * | 1980-11-03 | 1985-03-01 | ユニオン・カ−バイド・コ−ポレ−シヨン | 硬化し得るエポキシ樹脂含有組成物 |
| JPH0418460A (ja) * | 1990-05-11 | 1992-01-22 | Kansai Paint Co Ltd | カチオン電着塗料用樹脂組成物 |
| US5268489A (en) * | 1991-06-26 | 1993-12-07 | Union Carbide Chemicals & Plastics Technology Corporation | Production of unsaturated cycloaliphatic esters and derivatives thereof |
| US5948922A (en) * | 1997-02-20 | 1999-09-07 | Cornell Research Foundation, Inc. | Compounds with substituted cyclic hydrocarbon moieties linked by secondary or tertiary oxycarbonyl containing moiety providing reworkable cured thermosets |
| US20030059618A1 (en) * | 2001-03-23 | 2003-03-27 | Hideyuke Takai | Method of producing epoxy compound, epoxy resin composition and its applications, ultraviolet rays-curable can-coating composition and method of producing coated metal can |
| US6916890B1 (en) * | 2001-10-09 | 2005-07-12 | Henkel Corporation | Thermally reworkable epoxy resins and compositions based thereon |
-
2004
- 2004-09-10 KR KR1020067008596A patent/KR20060113912A/ko not_active Ceased
- 2004-09-10 JP JP2006537988A patent/JP2007510772A/ja active Pending
- 2004-09-10 BR BRPI0415812 patent/BRPI0415812A/pt not_active IP Right Cessation
- 2004-09-10 CN CNA2004800322989A patent/CN1875045A/zh active Pending
- 2004-09-10 WO PCT/US2004/029996 patent/WO2005044890A1/en not_active Ceased
- 2004-09-10 US US10/575,286 patent/US20070042191A1/en not_active Abandoned
- 2004-09-10 EP EP04788740A patent/EP1682599A1/en not_active Withdrawn
- 2004-09-20 TW TW93128404A patent/TW200523288A/zh unknown
- 2004-11-02 AR ARP040104029 patent/AR046438A1/es not_active Application Discontinuation
Patent Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5981329A (ja) * | 1982-09-30 | 1984-05-11 | ユニオン、カーバイド、コーポレーシヨン | 硬化し得るエポキシ樹脂含有成形組成物 |
| JPS62230861A (ja) * | 1985-12-19 | 1987-10-09 | ユニオン・カ−バイド・コ−ポレ−シヨン | 光硬化性相似被覆組成物 |
| JPS63261259A (ja) * | 1987-04-06 | 1988-10-27 | チバ−ガイギー アクチエンゲゼルシヤフト | 光構造性塗膜の製造方法 |
| JPH10251375A (ja) * | 1997-03-06 | 1998-09-22 | Ciba Specialty Chem Holding Inc | α−グリコール基含有グリシジル化合物 |
| JP2000159764A (ja) * | 1998-11-24 | 2000-06-13 | Ciba Specialty Chem Holding Inc | ピペラジノン誘導体 |
| JP2001200200A (ja) * | 1999-11-10 | 2001-07-24 | Vantico Ag | 硬化性組成物 |
| JP2002338659A (ja) * | 2001-05-14 | 2002-11-27 | Daicel Chem Ind Ltd | 液状エポキシ樹脂組成物及びその用途 |
| JP2002371073A (ja) * | 2001-06-12 | 2002-12-26 | Asahi Kasei Corp | エポキシ含有脂環式エステルの製法 |
| JP2003176333A (ja) * | 2001-08-23 | 2003-06-24 | General Electric Co <Ge> | エポキシ樹脂組成物、該組成物で封入された固体素子デバイス及び封入方法 |
| JP2003342268A (ja) * | 2002-05-28 | 2003-12-03 | Nippon Kasei Chem Co Ltd | エポキシ基末端(メタ)アクリレートの製造方法 |
| JP2004067947A (ja) * | 2002-08-08 | 2004-03-04 | Nippon Soda Co Ltd | 光触媒層形成用塗布液および光触媒担持構造体 |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006241180A (ja) * | 2005-02-28 | 2006-09-14 | Daicel Chem Ind Ltd | 紫外線硬化型缶用塗料組成物、塗装金属板、および塗装金属缶 |
| JP2010241942A (ja) * | 2009-04-03 | 2010-10-28 | Nippon Kayaku Co Ltd | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
| JP2011016880A (ja) * | 2009-07-07 | 2011-01-27 | Nippon Kayaku Co Ltd | 光半導体封止用硬化性樹脂組成物、及びその硬化物 |
| JP2011079794A (ja) * | 2009-10-09 | 2011-04-21 | Nippon Kayaku Co Ltd | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
| WO2011078205A1 (ja) * | 2009-12-24 | 2011-06-30 | 日本化薬株式会社 | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物、並びに光半導体装置 |
| WO2011078322A1 (ja) * | 2009-12-24 | 2011-06-30 | 日本化薬株式会社 | エポキシ樹脂組成物、硬化性樹脂組成物、およびその硬化物 |
| JP5559207B2 (ja) * | 2009-12-24 | 2014-07-23 | 日本化薬株式会社 | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物、並びに光半導体装置 |
| JP5615847B2 (ja) * | 2009-12-24 | 2014-10-29 | 日本化薬株式会社 | エポキシ樹脂組成物、硬化性樹脂組成物、およびその硬化物 |
| WO2011145733A1 (ja) * | 2010-05-21 | 2011-11-24 | 日本化薬株式会社 | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
| JP5878865B2 (ja) * | 2010-05-21 | 2016-03-08 | 日本化薬株式会社 | ジオレフィン化合物、エポキシ樹脂、硬化性樹脂組成物及びその硬化物 |
Also Published As
| Publication number | Publication date |
|---|---|
| TW200523288A (en) | 2005-07-16 |
| KR20060113912A (ko) | 2006-11-03 |
| AR046438A1 (es) | 2005-12-07 |
| WO2005044890A1 (en) | 2005-05-19 |
| CN1875045A (zh) | 2006-12-06 |
| EP1682599A1 (en) | 2006-07-26 |
| US20070042191A1 (en) | 2007-02-22 |
| BRPI0415812A (pt) | 2006-12-26 |
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