CA2957830C - High tg epoxy formulation with good thermal properties - Google Patents
High tg epoxy formulation with good thermal properties Download PDFInfo
- Publication number
- CA2957830C CA2957830C CA2957830A CA2957830A CA2957830C CA 2957830 C CA2957830 C CA 2957830C CA 2957830 A CA2957830 A CA 2957830A CA 2957830 A CA2957830 A CA 2957830A CA 2957830 C CA2957830 C CA 2957830C
- Authority
- CA
- Canada
- Prior art keywords
- varnish
- epoxy resin
- resin
- prepreg
- weight basis
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 32
- 239000004593 Epoxy Substances 0.000 title description 19
- 238000009472 formulation Methods 0.000 title description 6
- 239000002966 varnish Substances 0.000 claims abstract description 119
- 239000003822 epoxy resin Substances 0.000 claims abstract description 76
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 76
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229940106691 bisphenol a Drugs 0.000 claims abstract description 34
- 239000004843 novolac epoxy resin Substances 0.000 claims abstract description 27
- 229920005989 resin Polymers 0.000 claims description 49
- 239000011347 resin Substances 0.000 claims description 49
- 239000003063 flame retardant Substances 0.000 claims description 24
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 20
- 239000004848 polyfunctional curative Substances 0.000 claims description 20
- 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 description 16
- 239000010949 copper Substances 0.000 claims description 12
- 229910052802 copper Inorganic materials 0.000 claims description 11
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical group C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 10
- 150000004982 aromatic amines Chemical group 0.000 claims description 10
- BZQKBFHEWDPQHD-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene Chemical group BrC1=C(Br)C(Br)=C(Br)C(Br)=C1CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BZQKBFHEWDPQHD-UHFFFAOYSA-N 0.000 claims description 8
- 230000001588 bifunctional effect Effects 0.000 claims description 6
- 239000002131 composite material Substances 0.000 claims description 4
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 description 28
- 239000004744 fabric Substances 0.000 description 19
- 239000011521 glass Substances 0.000 description 19
- 238000004519 manufacturing process Methods 0.000 description 16
- 239000002904 solvent Substances 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 239000000945 filler Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000011342 resin composition Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229920001971 elastomer Polymers 0.000 description 7
- 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 7
- 229920003986 novolac Polymers 0.000 description 7
- 229920001187 thermosetting polymer Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 239000002841 Lewis acid Substances 0.000 description 6
- 239000011889 copper foil Substances 0.000 description 6
- 150000007517 lewis acids Chemical class 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- -1 for example Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 235000012239 silicon dioxide Nutrition 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 239000011162 core material Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 125000000466 oxiranyl group Chemical group 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 229910002026 crystalline silica Inorganic materials 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- PETRWTHZSKVLRE-UHFFFAOYSA-N 2-Methoxy-4-methylphenol Chemical compound COC1=CC(C)=CC=C1O PETRWTHZSKVLRE-UHFFFAOYSA-N 0.000 description 2
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical group O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000486634 Bena Species 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920000459 Nitrile rubber Polymers 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 239000007850 fluorescent dye Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000002648 laminated material Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000011236 particulate material Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 229920006380 polyphenylene oxide Polymers 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- IVORCBKUUYGUOL-UHFFFAOYSA-N 1-ethynyl-2,4-dimethoxybenzene Chemical compound COC1=CC=C(C#C)C(OC)=C1 IVORCBKUUYGUOL-UHFFFAOYSA-N 0.000 description 1
- LIAWCKFOFPPVGF-UHFFFAOYSA-N 2-ethyladamantane Chemical compound C1C(C2)CC3CC1C(CC)C2C3 LIAWCKFOFPPVGF-UHFFFAOYSA-N 0.000 description 1
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 description 1
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 1
- MXJGWNPVKBVVTM-UHFFFAOYSA-N 5-tert-butyl-1,3-benzoxazole Chemical compound CC(C)(C)C1=CC=C2OC=NC2=C1 MXJGWNPVKBVVTM-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 102100028890 E3 ubiquitin-protein ligase synoviolin Human genes 0.000 description 1
- 101000838967 Homo sapiens E3 ubiquitin-protein ligase synoviolin Proteins 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001665 Poly-4-vinylphenol Polymers 0.000 description 1
- 229920000388 Polyphosphate Polymers 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- QBLDFAIABQKINO-UHFFFAOYSA-N barium borate Chemical compound [Ba+2].[O-]B=O.[O-]B=O QBLDFAIABQKINO-UHFFFAOYSA-N 0.000 description 1
- 150000005130 benzoxazines Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- LKAVYBZHOYOUSX-UHFFFAOYSA-N buta-1,3-diene;2-methylprop-2-enoic acid;styrene Chemical group C=CC=C.CC(=C)C(O)=O.C=CC1=CC=CC=C1 LKAVYBZHOYOUSX-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- CETPSERCERDGAM-UHFFFAOYSA-N ceric oxide Chemical compound O=[Ce]=O CETPSERCERDGAM-UHFFFAOYSA-N 0.000 description 1
- 229910000422 cerium(IV) oxide Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011152 fibreglass Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- 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
- 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
- C08J5/249—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs characterised by the additives used in the prepolymer mixture
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L63/04—Epoxynovolacs
-
- 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
- C09D163/04—Epoxynovolacs
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
- C09J163/04—Epoxynovolacs
-
- 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
-
- 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
- H05K3/00—Apparatus or processes for manufacturing printed circuits
-
- 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
- C08J2363/04—Epoxynovolacs
-
- 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
- C08J2463/00—Characterised by the use of epoxy resins; Derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
-
- 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
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Inorganic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Epoxy Resins (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462051051P | 2014-09-16 | 2014-09-16 | |
| US62/051,051 | 2014-09-16 | ||
| US14/743,093 | 2015-06-18 | ||
| US14/743,093 US9822227B2 (en) | 2014-09-16 | 2015-06-18 | High Tg epoxy formulation with good thermal properties |
| PCT/US2015/037247 WO2016043825A1 (en) | 2014-09-16 | 2015-06-23 | High tg epoxy formulation with good thermal properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2957830A1 CA2957830A1 (en) | 2016-03-24 |
| CA2957830C true CA2957830C (en) | 2019-01-08 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2957830A Active CA2957830C (en) | 2014-09-16 | 2015-06-23 | High tg epoxy formulation with good thermal properties |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US9822227B2 (enExample) |
| EP (1) | EP3194516B1 (enExample) |
| JP (2) | JP7134627B2 (enExample) |
| KR (1) | KR102447582B1 (enExample) |
| CN (1) | CN107075294B (enExample) |
| CA (1) | CA2957830C (enExample) |
| MY (1) | MY178642A (enExample) |
| SG (1) | SG11201700654XA (enExample) |
| TW (1) | TWI561594B (enExample) |
| WO (1) | WO2016043825A1 (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9822227B2 (en) | 2014-09-16 | 2017-11-21 | Isola Usa Corp. | High Tg epoxy formulation with good thermal properties |
| TWI709483B (zh) * | 2018-01-22 | 2020-11-11 | 聯茂電子股份有限公司 | 層壓板以及印刷電路板 |
| CN111500270A (zh) * | 2019-12-30 | 2020-08-07 | 大庆石油管理局有限公司 | 一种油水井井下修井用高效树脂封堵液 |
| CN111961314A (zh) * | 2020-08-26 | 2020-11-20 | 深圳先进电子材料国际创新研究院 | 一种电子封装材料及其制备方法和应用 |
| US11359062B1 (en) | 2021-01-20 | 2022-06-14 | Thintronics, Inc. | Polymer compositions and their uses |
| US11596066B1 (en) | 2022-03-22 | 2023-02-28 | Thintronics. Inc. | Materials for printed circuit boards |
| IT202300022308A1 (it) * | 2023-10-25 | 2025-04-25 | Antonio ARONNE | Materiale composito termoisolante e resistente alla fiamma a base di resina epossidica contenente particelle di titania funzionalizzate con silano |
Family Cites Families (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4455250A (en) | 1981-01-12 | 1984-06-19 | American Cyanamid Company | Stable liquid hard surface cleanser composition containing DGH and a quaternary germicide |
| US4550128A (en) * | 1984-04-16 | 1985-10-29 | International Business Machines Corporation | Epoxy composition |
| US5364700A (en) * | 1985-12-27 | 1994-11-15 | Amoco Corporation | Prepregable resin composition and composite |
| JPH07121989B2 (ja) * | 1987-08-13 | 1995-12-25 | 東邦レーヨン株式会社 | 型成形用プリプレグ |
| JPH05295083A (ja) * | 1992-04-24 | 1993-11-09 | Nippon Kayaku Co Ltd | 型用エポキシ樹脂組成物及びそれから得られる樹脂型 |
| JP3216291B2 (ja) * | 1993-01-13 | 2001-10-09 | 東邦テナックス株式会社 | 難燃性エポキシ樹脂組成物及びプリプレグ |
| AU728470B2 (en) | 1996-02-14 | 2001-01-11 | Stepan Company | Reduced residue hard surface cleaner comprising hydrotrope |
| US6159916A (en) | 1998-06-12 | 2000-12-12 | The Clorox Company | Shower rinsing composition |
| US6204456B1 (en) | 1998-09-24 | 2001-03-20 | International Business Machines Corporation | Filling open through holes in a multilayer board |
| US6528218B1 (en) | 1998-12-15 | 2003-03-04 | International Business Machines Corporation | Method of fabricating circuitized structures |
| ATE308585T1 (de) | 1999-12-13 | 2005-11-15 | Dow Global Technologies Inc | Feuerhemmende phosporenthaltende epoxidharzzusammensetzung |
| JP2001240836A (ja) | 2000-02-29 | 2001-09-04 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物および接着剤付き金属箔 |
| EP1275674B1 (en) | 2000-04-21 | 2007-04-04 | Mitsubishi Rayon Co., Ltd. | Epoxy resin composition and prepreg made with the epoxy resin composition |
| JP2006131920A (ja) | 2000-04-21 | 2006-05-25 | Mitsubishi Rayon Co Ltd | エポキシ樹脂組成物及び該エポキシ樹脂組成物を使用したプリプレグ |
| JP2002080559A (ja) * | 2000-09-06 | 2002-03-19 | Sumitomo Bakelite Co Ltd | インターポーザ用エポキシ樹脂組成物、プリプレグ及びそれを用いた銅張積層板 |
| US7070861B2 (en) | 2000-12-18 | 2006-07-04 | Mitsubishi Rayon Co., Ltd. | Flame retardant epoxy resin composition, and prepreg and fiber-reinforced composite materials made by using the composition |
| JP5078208B2 (ja) * | 2001-09-25 | 2012-11-21 | 三菱レイヨン株式会社 | エポキシ樹脂組成物及び該エポキシ樹脂組成物を使用したプリプレグ |
| US20030158337A1 (en) * | 2001-12-05 | 2003-08-21 | Isola Laminate Systems Corp. | Thermosetting resin composition for high performance laminates |
| US20060115440A1 (en) | 2004-09-07 | 2006-06-01 | Arata Andrew B | Silver dihydrogen citrate compositions |
| US7687556B2 (en) | 2004-09-28 | 2010-03-30 | Isola Usa Corp. | Flame retardant compositions |
| US8129456B2 (en) | 2004-09-28 | 2012-03-06 | Isola Usa Corp. | Flame retardant compositions with a phosphorated compound |
| JP2006152099A (ja) | 2004-11-29 | 2006-06-15 | Toray Ind Inc | プリプレグ |
| JP5411406B2 (ja) * | 2005-07-13 | 2014-02-12 | 三菱レイヨン株式会社 | プリプレグ |
| JP2007314761A (ja) | 2006-04-28 | 2007-12-06 | Hitachi Chem Co Ltd | エポキシ樹脂組成物、ならびにそれを用いたプリプレグ、金属張積層板および多層プリント配線板 |
| EP1948769B1 (en) | 2006-07-31 | 2009-03-25 | Reckitt Benckiser (UK) LIMITED | Improved hard surface cleaning compositions |
| JP2010526907A (ja) * | 2007-05-09 | 2010-08-05 | ダウ グローバル テクノロジーズ インコーポレイティド | 過剰のエポキシレジンを含むエポキシ熱硬化性組成物およびその製造方法 |
| TWI350716B (en) * | 2008-12-29 | 2011-10-11 | Nanya Plastics Corp | High thermal conductivity, halogen-free flame-retardent resin composition and its pre-impregnated and coating materials for printed circuit boards |
| JP5487634B2 (ja) | 2009-02-10 | 2014-05-07 | 東亞合成株式会社 | フレキシブル印刷配線板用難燃性接着剤組成物及びそれを用いたフレキシブル印刷配線板 |
| EP2578613B8 (en) * | 2010-05-31 | 2018-12-19 | Hitachi Chemical Company, Ltd. | Epoxy resin composition and pre-preg, support-provided resin film, metallic foil clad laminate plate and multilayer printed circuit board utilizing said composition |
| EP2598573A1 (en) * | 2010-07-30 | 2013-06-05 | Dow Global Technologies LLC | Curable compositions |
| CN102633990A (zh) * | 2012-04-05 | 2012-08-15 | 广东生益科技股份有限公司 | 环氧树脂组合物及使用其制作的半固化片与覆铜箔层压板 |
| TWI545155B (zh) | 2012-06-05 | 2016-08-11 | 三菱麗陽股份有限公司 | 環氧樹脂組成物、預浸絲束、複合材料補強壓力容器以及鋼腱 |
| JP6128311B2 (ja) * | 2013-02-12 | 2017-05-17 | パナソニックＩｐマネジメント株式会社 | 樹脂組成物、樹脂ワニス、プリプレグ、金属張積層板、及びプリント配線板 |
| CN104119639B (zh) * | 2013-04-24 | 2016-08-03 | 台光电子材料(昆山)有限公司 | 无卤素树脂组合物及应用其的铜箔基板及印刷电路板 |
| GB2535075B (en) | 2014-06-23 | 2022-03-30 | Energizer Auto Inc | Cleaning composition having improved vertical cling |
| US9822227B2 (en) * | 2014-09-16 | 2017-11-21 | Isola Usa Corp. | High Tg epoxy formulation with good thermal properties |
-
2015
- 2015-06-18 US US14/743,093 patent/US9822227B2/en active Active
- 2015-06-23 SG SG11201700654XA patent/SG11201700654XA/en unknown
- 2015-06-23 KR KR1020177007277A patent/KR102447582B1/ko active Active
- 2015-06-23 WO PCT/US2015/037247 patent/WO2016043825A1/en not_active Ceased
- 2015-06-23 CA CA2957830A patent/CA2957830C/en active Active
- 2015-06-23 EP EP15741397.2A patent/EP3194516B1/en active Active
- 2015-06-23 CN CN201580049319.6A patent/CN107075294B/zh active Active
- 2015-06-23 MY MYPI2017700599A patent/MY178642A/en unknown
- 2015-06-23 JP JP2017514684A patent/JP7134627B2/ja active Active
- 2015-07-09 TW TW104122396A patent/TWI561594B/zh active
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2017
- 2017-10-17 US US15/786,131 patent/US10364332B2/en active Active
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2019
- 2019-07-18 US US16/515,127 patent/US11155687B2/en active Active
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2020
- 2020-08-20 JP JP2020139551A patent/JP7084966B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| KR102447582B1 (ko) | 2022-09-26 |
| JP7084966B2 (ja) | 2022-06-15 |
| US20200181342A1 (en) | 2020-06-11 |
| TWI561594B (en) | 2016-12-11 |
| US9822227B2 (en) | 2017-11-21 |
| SG11201700654XA (en) | 2017-04-27 |
| TW201612264A (en) | 2016-04-01 |
| CA2957830A1 (en) | 2016-03-24 |
| EP3194516A1 (en) | 2017-07-26 |
| JP7134627B2 (ja) | 2022-09-12 |
| MY178642A (en) | 2020-10-19 |
| US20160075839A1 (en) | 2016-03-17 |
| US20180251618A1 (en) | 2018-09-06 |
| CN107075294B (zh) | 2019-12-31 |
| EP3194516B1 (en) | 2020-08-05 |
| US10364332B2 (en) | 2019-07-30 |
| JP2017531067A (ja) | 2017-10-19 |
| WO2016043825A1 (en) | 2016-03-24 |
| CN107075294A (zh) | 2017-08-18 |
| US11155687B2 (en) | 2021-10-26 |
| JP2021001337A (ja) | 2021-01-07 |
| KR20170057274A (ko) | 2017-05-24 |
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