CA2582360A1 - Amphiphilic block copolymer-toughened epoxy resins and electrical laminates made therefrom - Google Patents
Amphiphilic block copolymer-toughened epoxy resins and electrical laminates made therefrom Download PDFInfo
- Publication number
- CA2582360A1 CA2582360A1 CA002582360A CA2582360A CA2582360A1 CA 2582360 A1 CA2582360 A1 CA 2582360A1 CA 002582360 A CA002582360 A CA 002582360A CA 2582360 A CA2582360 A CA 2582360A CA 2582360 A1 CA2582360 A1 CA 2582360A1
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- composition
- block
- block copolymer
- immiscible
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 141
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 118
- 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 title description 21
- 239000000203 mixture Substances 0.000 claims abstract description 120
- 229920001400 block copolymer Polymers 0.000 claims abstract description 98
- 229920000570 polyether Polymers 0.000 claims abstract description 72
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 71
- 239000004593 Epoxy Substances 0.000 claims abstract description 48
- 229920000469 amphiphilic block copolymer Polymers 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 239000000178 monomer Substances 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- -1 polybutylene Polymers 0.000 claims description 52
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 230000008569 process Effects 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 12
- 229920001519 homopolymer Polymers 0.000 claims description 8
- 239000005977 Ethylene Substances 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- 239000002966 varnish Substances 0.000 claims description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
- 229920001748 polybutylene Polymers 0.000 claims description 5
- 230000003014 reinforcing effect Effects 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 239000004744 fabric Substances 0.000 claims description 4
- 239000003365 glass fiber Substances 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 claims description 2
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 150000001469 hydantoins Chemical class 0.000 claims description 2
- 150000003949 imides Chemical class 0.000 claims description 2
- QCGKUFZYSPBMAY-UHFFFAOYSA-N methyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1C(C(=O)OC)CCC2OC21 QCGKUFZYSPBMAY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003921 oil Substances 0.000 claims description 2
- 229920000098 polyolefin Polymers 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 229920006305 unsaturated polyester Polymers 0.000 claims description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- 229920000359 diblock copolymer Polymers 0.000 abstract description 22
- 229920000428 triblock copolymer Polymers 0.000 abstract description 10
- 229920005989 resin Polymers 0.000 description 59
- 239000011347 resin Substances 0.000 description 59
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
- 239000002904 solvent Substances 0.000 description 21
- 229920001577 copolymer Polymers 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 229920001187 thermosetting polymer Polymers 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000011342 resin composition Substances 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N Bisphenol A Natural products C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000693 micelle Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000012745 toughening agent Substances 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
- 125000003700 epoxy group Chemical group 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 229920003986 novolac Polymers 0.000 description 7
- 238000012545 processing Methods 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 229920002319 Poly(methyl acrylate) Polymers 0.000 description 6
- 229940106691 bisphenol a Drugs 0.000 description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 6
- 239000004327 boric acid Substances 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000011159 matrix material Substances 0.000 description 6
- 238000001338 self-assembly Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000003475 lamination Methods 0.000 description 5
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
- 239000002841 Lewis acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 150000007517 lewis acids Chemical class 0.000 description 4
- 239000005022 packaging material Substances 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 3
- 208000037427 Beta-propeller protein-associated neurodegeneration Diseases 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000001721 carbon Chemical class 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000005553 drilling Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 201000007614 neurodegeneration with brain iron accumulation 5 Diseases 0.000 description 3
- 239000004848 polyfunctional curative Substances 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- 235000013772 propylene glycol Nutrition 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 2
- ZFMOJHVRFMOIGF-UHFFFAOYSA-N 2,4,6-trimethoxy-1,3,5,2,4,6-trioxatriborinane Chemical compound COB1OB(OC)OB(OC)O1 ZFMOJHVRFMOIGF-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 239000006145 Eagle's minimal essential medium Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000011889 copper foil Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
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- 239000000428 dust Substances 0.000 description 2
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- 235000011187 glycerol Nutrition 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- 230000000877 morphologic effect Effects 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical class C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
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- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
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- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
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- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
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- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/244—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using glass fibres
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2363/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Manufacturing & Machinery (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
- Reinforced Plastic Materials (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62661104P | 2004-11-10 | 2004-11-10 | |
| US60/626,611 | 2004-11-10 | ||
| PCT/US2005/039963 WO2006052727A1 (en) | 2004-11-10 | 2005-11-02 | Amphiphilic block copolymer-toughened epoxy resins and electrical laminates made therefrom |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2582360A1 true CA2582360A1 (en) | 2006-05-18 |
Family
ID=35770865
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002582360A Abandoned CA2582360A1 (en) | 2004-11-10 | 2005-11-02 | Amphiphilic block copolymer-toughened epoxy resins and electrical laminates made therefrom |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7923073B2 (https=) |
| EP (1) | EP1814948B1 (https=) |
| JP (1) | JP5248860B2 (https=) |
| KR (1) | KR101227201B1 (https=) |
| CN (1) | CN101056933B (https=) |
| AT (1) | ATE453688T1 (https=) |
| BR (1) | BRPI0516702A (https=) |
| CA (1) | CA2582360A1 (https=) |
| DE (1) | DE602005018680D1 (https=) |
| ES (1) | ES2337598T3 (https=) |
| MX (1) | MX2007005597A (https=) |
| NO (1) | NO20071727L (https=) |
| RU (1) | RU2395545C2 (https=) |
| TW (1) | TWI400296B (https=) |
| WO (1) | WO2006052727A1 (https=) |
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| KR101129115B1 (ko) * | 2004-04-02 | 2012-03-23 | 리전츠 오브 더 유니버시티 오브 미네소타 | 양친매성 블럭 공중합체 강인화 열경화성 수지 |
| KR101226377B1 (ko) * | 2004-11-10 | 2013-01-24 | 다우 글로벌 테크놀로지스 엘엘씨 | 양친매성 블록 공중합체-강인화된 에폭시 수지 및 그로부터제조된 분말 코팅 |
| JP4634856B2 (ja) * | 2005-05-12 | 2011-02-16 | 利昌工業株式会社 | 白色プリプレグ、白色積層板、及び金属箔張り白色積層板 |
| US9096790B2 (en) | 2007-03-22 | 2015-08-04 | Hexion Inc. | Low temperature coated particles comprising a curable liquid and a reactive powder for use as proppants or in gravel packs, methods for making and using the same |
| JP5336485B2 (ja) | 2007-08-02 | 2013-11-06 | ダウ グローバル テクノロジーズ エルエルシー | 熱硬化性ポリマーの性能を向上させるための両親媒性ブロックコポリマーおよび無機ナノフィラー |
| US8492482B2 (en) * | 2007-12-10 | 2013-07-23 | Arkema Inc. | Acrylic-based rubber modified thermoset composition |
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| KR20160007668A (ko) | 2008-04-14 | 2016-01-20 | 블루 큐브 아이피 엘엘씨 | 분말 피복 분야에 유용한 에폭시-이미다졸 촉매 |
| EP2110397A1 (de) | 2008-04-16 | 2009-10-21 | Sika Technology AG | Auf amphiphilen Block-Copolymer basierendes Polyurethan-Polymer und dessen Verwendung als Schlagzähigkeitsmodifikator |
| JP2011521151A (ja) * | 2008-05-16 | 2011-07-21 | ダウ グローバル テクノロジーズ エル エルエルシー | 風車プロペラ羽根及びその製造方法 |
| EP2128182A1 (de) | 2008-05-28 | 2009-12-02 | Sika Technology AG | Hitzehärtende Epoxidharzzusammensetzung enthaltend einen Beschleuniger mit Heteroatomen |
| ATE461953T1 (de) | 2008-07-17 | 2010-04-15 | Sika Technology Ag | Haftvermittlerverbindungen für beölten stahl |
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| EP2182025B1 (de) | 2008-10-31 | 2010-10-06 | Sika Technology AG | Hitzehärtende Epoxidharzzusammensetzungen einsetzbar als Rohbauklebstoff oder Strukturschaum |
| TWI423741B (zh) * | 2009-02-13 | 2014-01-11 | Iteq Corp | An epoxy resin composition and a film and a substrate made of the epoxy resin composition |
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| BRPI0924000B1 (pt) * | 2009-03-09 | 2019-08-06 | Dow Global Technologies Llc | Composição termofixável, produto termofixo e processo para preparar uma composição termofixável |
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| EP2365011A1 (de) | 2010-03-02 | 2011-09-14 | Sika Technology AG | Aminogruppen - terminierter Schlagzähigkeitsmodifikator und dessen Verwendungen in Epoxidharzzusammensetzungen |
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| US4119609A (en) | 1977-03-28 | 1978-10-10 | Shell Oil Company | Curable epoxy-carboxylic acid adducts |
| US4431782A (en) | 1981-07-27 | 1984-02-14 | The Dow Chemical Company | Process for the preparation of radiation-curable, water-thinnable vinyl ester resins |
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-
2005
- 2005-11-02 RU RU2007121650/04A patent/RU2395545C2/ru not_active IP Right Cessation
- 2005-11-02 EP EP05818062A patent/EP1814948B1/en not_active Expired - Lifetime
- 2005-11-02 KR KR1020077010527A patent/KR101227201B1/ko not_active Expired - Fee Related
- 2005-11-02 MX MX2007005597A patent/MX2007005597A/es active IP Right Grant
- 2005-11-02 WO PCT/US2005/039963 patent/WO2006052727A1/en not_active Ceased
- 2005-11-02 JP JP2007541252A patent/JP5248860B2/ja not_active Expired - Fee Related
- 2005-11-02 DE DE602005018680T patent/DE602005018680D1/de not_active Expired - Lifetime
- 2005-11-02 CA CA002582360A patent/CA2582360A1/en not_active Abandoned
- 2005-11-02 CN CN2005800382698A patent/CN101056933B/zh not_active Expired - Fee Related
- 2005-11-02 US US11/663,802 patent/US7923073B2/en not_active Expired - Fee Related
- 2005-11-02 ES ES05818062T patent/ES2337598T3/es not_active Expired - Lifetime
- 2005-11-02 BR BRPI0516702-7A patent/BRPI0516702A/pt not_active IP Right Cessation
- 2005-11-02 AT AT05818062T patent/ATE453688T1/de active
- 2005-11-09 TW TW094139243A patent/TWI400296B/zh not_active IP Right Cessation
-
2007
- 2007-04-02 NO NO20071727A patent/NO20071727L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20071727L (no) | 2007-08-08 |
| JP5248860B2 (ja) | 2013-07-31 |
| KR101227201B1 (ko) | 2013-01-28 |
| EP1814948A1 (en) | 2007-08-08 |
| HK1112930A1 (en) | 2008-09-19 |
| CN101056933A (zh) | 2007-10-17 |
| BRPI0516702A (pt) | 2008-09-16 |
| RU2007121650A (ru) | 2008-12-20 |
| MX2007005597A (es) | 2007-05-23 |
| US20080213489A1 (en) | 2008-09-04 |
| RU2395545C2 (ru) | 2010-07-27 |
| EP1814948B1 (en) | 2009-12-30 |
| JP2008519886A (ja) | 2008-06-12 |
| ES2337598T3 (es) | 2010-04-27 |
| WO2006052727A1 (en) | 2006-05-18 |
| CN101056933B (zh) | 2012-11-21 |
| DE602005018680D1 (de) | 2010-02-11 |
| KR20070084111A (ko) | 2007-08-24 |
| US7923073B2 (en) | 2011-04-12 |
| ATE453688T1 (de) | 2010-01-15 |
| TWI400296B (zh) | 2013-07-01 |
| TW200624500A (en) | 2006-07-16 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20140805 |