CA2810709A1 - Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material - Google Patents
Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material Download PDFInfo
- Publication number
- CA2810709A1 CA2810709A1 CA 2810709 CA2810709A CA2810709A1 CA 2810709 A1 CA2810709 A1 CA 2810709A1 CA 2810709 CA2810709 CA 2810709 CA 2810709 A CA2810709 A CA 2810709A CA 2810709 A1 CA2810709 A1 CA 2810709A1
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- prepreg
- resin composition
- temperature
- weight parts
- 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
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 194
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 194
- 239000000203 mixture Substances 0.000 title claims abstract description 137
- -1 prepreg Substances 0.000 title claims abstract description 22
- 239000000463 material Substances 0.000 title claims description 102
- 239000003733 fiber-reinforced composite Substances 0.000 title claims description 82
- 150000001412 amines Chemical class 0.000 claims abstract description 21
- 239000004202 carbamide Substances 0.000 claims abstract description 18
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims abstract description 17
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims description 103
- 239000011347 resin Substances 0.000 claims description 103
- 239000012783 reinforcing fiber Substances 0.000 claims description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 230000009477 glass transition Effects 0.000 claims description 16
- 230000001965 increasing effect Effects 0.000 claims description 16
- 239000004744 fabric Substances 0.000 claims description 15
- 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 description 10
- 239000000835 fiber Substances 0.000 claims description 10
- 238000005470 impregnation Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000010030 laminating Methods 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 4
- VAUOPRZOGIRSMI-UHFFFAOYSA-N n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC1=CC=CC=C1 VAUOPRZOGIRSMI-UHFFFAOYSA-N 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 230000035699 permeability Effects 0.000 claims description 3
- 229930185605 Bisphenol Natural products 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 238000007872 degassing Methods 0.000 claims description 2
- 239000011159 matrix material Substances 0.000 description 47
- 238000001723 curing Methods 0.000 description 46
- 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 34
- 229920003319 Araldite® Polymers 0.000 description 25
- 239000003570 air Substances 0.000 description 19
- 229920000049 Carbon (fiber) Polymers 0.000 description 18
- 239000004917 carbon fiber Substances 0.000 description 18
- 238000000465 moulding Methods 0.000 description 18
- 230000007613 environmental effect Effects 0.000 description 17
- 238000000034 method Methods 0.000 description 17
- 239000011800 void material Substances 0.000 description 17
- 238000005259 measurement Methods 0.000 description 16
- 238000009472 formulation Methods 0.000 description 14
- 238000003475 lamination Methods 0.000 description 12
- 239000004848 polyfunctional curative Substances 0.000 description 12
- 229920005992 thermoplastic resin Polymers 0.000 description 12
- 238000003860 storage Methods 0.000 description 11
- 229920001342 Bakelite® Polymers 0.000 description 10
- 239000004637 bakelite Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 230000002708 enhancing effect Effects 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 230000001133 acceleration Effects 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- 238000000691 measurement method Methods 0.000 description 3
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 3
- 239000011208 reinforced composite material Substances 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000000748 compression moulding Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 238000013035 low temperature curing Methods 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 2
- 238000013001 point bending Methods 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- IVSZLXZYQVIEFR-UHFFFAOYSA-N 1,3-Dimethylbenzene Natural products CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- DXBXIDZYBDDOJV-UHFFFAOYSA-N 2,3,3-trimethyl-2-phenyl-1h-indene Chemical group CC1(C)C2=CC=CC=C2CC1(C)C1=CC=CC=C1 DXBXIDZYBDDOJV-UHFFFAOYSA-N 0.000 description 1
- JBCUKQQIWSWEOK-UHFFFAOYSA-N 2-(benzenesulfonyl)aniline Chemical compound NC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 JBCUKQQIWSWEOK-UHFFFAOYSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- UKGDGZJDRRMVOO-UHFFFAOYSA-N 2-phenyl-3,4-di(propan-2-yl)aniline Chemical compound NC1=C(C(=C(C=C1)C(C)C)C(C)C)C1=CC=CC=C1 UKGDGZJDRRMVOO-UHFFFAOYSA-N 0.000 description 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 1
- ITNADJKYRCCJNX-UHFFFAOYSA-N 3-(2,3-diaminophenyl)sulfonylbenzene-1,2-diamine Chemical compound NC1=CC=CC(S(=O)(=O)C=2C(=C(N)C=CC=2)N)=C1N ITNADJKYRCCJNX-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 101100505905 Dictyostelium discoideum gtaF gene Proteins 0.000 description 1
- 235000015842 Hesperis Nutrition 0.000 description 1
- 235000012633 Iberis amara Nutrition 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- 239000004696 Poly ether ether ketone Substances 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004962 Polyamide-imide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000000816 ethylene group Polymers [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- JAYXSROKFZAHRQ-UHFFFAOYSA-N n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC=CC=1)CC1CO1 JAYXSROKFZAHRQ-UHFFFAOYSA-N 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- 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
- 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
- C08G59/28—Di-epoxy compounds containing acyclic nitrogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B37/00—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding
- B32B37/0007—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding involving treatment or provisions in order to avoid deformation or air inclusion, e.g. to improve surface quality
- B32B37/003—Methods or apparatus for laminating, e.g. by curing or by ultrasonic bonding involving treatment or provisions in order to avoid deformation or air inclusion, e.g. to improve surface quality to avoid air inclusion
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
-
- 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
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3227—Compounds containing acyclic nitrogen atoms
-
- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
-
- 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
-
- 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
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/21—Urea; Derivatives thereof, e.g. biuret
-
- 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/315—Compounds containing carbon-to-nitrogen triple bonds
- C08K5/3155—Dicyandiamide
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- 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
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
-
- 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
-
- 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
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Quality & Reliability (AREA)
- Reinforced Plastic Materials (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41123110P | 2010-11-08 | 2010-11-08 | |
| US61/411,231 | 2010-11-08 | ||
| US201161530173P | 2011-09-01 | 2011-09-01 | |
| US61/530,173 | 2011-09-01 | ||
| PCT/US2011/059610 WO2012064662A1 (en) | 2010-11-08 | 2011-11-07 | Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2810709A1 true CA2810709A1 (en) | 2012-05-18 |
Family
ID=46051258
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2810709 Abandoned CA2810709A1 (en) | 2010-11-08 | 2011-11-07 | Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US9957387B2 (enExample) |
| EP (1) | EP2637860B1 (enExample) |
| JP (1) | JP6007914B2 (enExample) |
| KR (1) | KR101825247B1 (enExample) |
| CN (1) | CN103201102B (enExample) |
| BR (1) | BR112013009345A2 (enExample) |
| CA (1) | CA2810709A1 (enExample) |
| RU (1) | RU2013126414A (enExample) |
| TW (1) | TW201229084A (enExample) |
| WO (1) | WO2012064662A1 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2013255534B2 (en) * | 2012-05-02 | 2017-02-23 | Nexans | A light weight cable |
| CN104583310B (zh) * | 2012-08-20 | 2017-04-05 | 三菱丽阳株式会社 | 环氧树脂组合物以及使用该环氧树脂组合物的膜、预浸料、纤维增强塑料 |
| GB201217210D0 (en) * | 2012-09-26 | 2012-11-07 | Blade Dynamics Ltd | A metod of forming a structural connection between a spar cap fairing for a wind turbine blade |
| TWI621639B (zh) | 2013-01-07 | 2018-04-21 | 東麗股份有限公司 | 環氧樹脂組成物及預浸漬物 |
| 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 |
| WO2014195799A2 (en) * | 2013-06-07 | 2014-12-11 | Toray Industries, Inc. | Fiber reinforced polymer composition enabling rapid-cycle void-free composite manufacturing |
| US9309353B2 (en) | 2013-08-09 | 2016-04-12 | The Boeing Company | Formulation methodology for distortional thermosets |
| GB201411586D0 (en) * | 2014-06-30 | 2014-08-13 | Hexcel Composites Ltd | Adhesive composition |
| EP3002304B1 (en) | 2014-10-03 | 2017-08-02 | Tokyo Ohka Kogyo Co., Ltd. | Curable composition |
| CN104388028A (zh) * | 2014-12-01 | 2015-03-04 | 南京大学 | 一种韧性耐高温环氧树脂粘合剂 |
| JP6511071B2 (ja) | 2014-12-09 | 2019-05-15 | 東京応化工業株式会社 | 硬化性組成物 |
| US10800894B2 (en) * | 2015-02-27 | 2020-10-13 | Toray Industries, Inc. | Resin supply material, preform, and method of producing fiber-reinforced resin |
| WO2017047225A1 (ja) * | 2015-09-17 | 2017-03-23 | 東レ株式会社 | エポキシ樹脂組成物、プリプレグおよび繊維強化複合材料 |
| CN108137839B (zh) | 2015-12-16 | 2021-07-06 | 东丽株式会社 | 预浸料坯、层压体、纤维增强复合材料、及纤维增强复合材料的制造方法 |
| WO2017163129A1 (en) * | 2016-03-24 | 2017-09-28 | Toray Industries, Inc. | Epoxy resin composition, prepreg, and fiber reinforced plastic material |
| KR101790112B1 (ko) * | 2016-03-29 | 2017-10-26 | 주식회사 한국카본 | 프레스 공법을 통한 차체부품 고속경화 프리프레그용 수지 조성물 및 이를 포함하는 프리프레그 제품 |
| WO2018005045A1 (en) * | 2016-06-27 | 2018-01-04 | Dow Global Technologies Llc | Storage stable epoxy prepregs from dicyandiamide solutions and methods for making the same |
| JP2019526650A (ja) * | 2016-08-26 | 2019-09-19 | 東レ株式会社 | エポキシ樹脂組成物、プリプレグ、及び繊維強化プラスチック材料 |
| JP6573029B2 (ja) * | 2017-05-10 | 2019-09-11 | 東レ株式会社 | 繊維強化複合材料の製造方法 |
| KR102341161B1 (ko) * | 2017-08-10 | 2021-12-20 | 도레이첨단소재 주식회사 | 저밀도 프리프레그 및 이를 포함하는 샌드위치 복합 성형품 |
| RU2655805C1 (ru) * | 2017-08-31 | 2018-05-29 | Акционерное общество "Препрег-Современные Композиционные Материалы" (АО "Препрег-СКМ") | Эпоксидное связующее, препрег на его основе и изделие, выполненное из него |
| ES3069884T3 (en) * | 2018-01-31 | 2026-06-11 | Toray Industries | Prepreg sheets and prepreg stacks useful for preparing low void content fiber-reinforced compostite materials |
| JP7209470B2 (ja) * | 2018-03-13 | 2023-01-20 | 帝人株式会社 | プリプレグ及び炭素繊維強化複合材料 |
| KR102562027B1 (ko) * | 2018-07-05 | 2023-07-31 | 도레이첨단소재 주식회사 | 섬유강화 복합재료용 에폭시 수지 조성물 및 이를 이용한 프리프레그 |
| JP7206993B2 (ja) * | 2019-02-18 | 2023-01-18 | 三菱ケミカル株式会社 | 炭素繊維強化複合材料用エポキシ樹脂組成物、プリプレグおよび炭素繊維強化複合材料 |
| EP3995536B1 (en) * | 2019-07-05 | 2025-06-18 | Toray Industries, Inc. | Prepreg and fiber-reinforced composite material |
| JP7487865B2 (ja) * | 2020-02-27 | 2024-05-21 | 国立大学法人東海国立大学機構 | ホース、ホースの製造方法、および、油圧式ポンプ |
| JP2023067809A (ja) * | 2021-10-29 | 2023-05-16 | 東レ株式会社 | エポキシ樹脂組成物、プリプレグおよび繊維強化複合材料 |
| CN114230974B (zh) * | 2021-12-14 | 2024-04-02 | 江苏兆鋆新材料股份有限公司 | 一种碳纤维环氧预浸料用增韧环氧树脂及其制备方法 |
| WO2026022814A1 (en) * | 2024-07-24 | 2026-01-29 | Israel Plastics & Rubber Center (1986) Ltd. | Epoxy compositions and products comprised thereof |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5230906A (en) | 1986-11-24 | 1993-07-27 | Polytex Plastic Sa | Method of and apparatus for manufacturing fiber-reinforced plastics articles |
| JPH0362821A (ja) * | 1989-07-31 | 1991-03-18 | Tonen Corp | エポキシ樹脂組成物 |
| WO1997031052A1 (en) * | 1996-02-21 | 1997-08-28 | Toray Industries, Inc. | Epoxy resin composition for fiber-reinforced composite material, yarn prepreg, and process and apparatus for preparing the same |
| CA2511566C (en) | 1998-05-20 | 2007-11-20 | Cytec Technology Corporation | Manufacture of void-free laminates and use thereof |
| JP4544656B2 (ja) | 1998-06-30 | 2010-09-15 | 東レ株式会社 | プリプレグおよび繊維強化複合材料 |
| WO2000053654A1 (fr) | 1999-03-11 | 2000-09-14 | Toray Industries, Inc. | Composition de resine epoxy, composition de resine epoxy pour materiau composite a fibres, et materiau composite a fibres contenant ladite composition |
| EP1174250B1 (fr) * | 2000-07-17 | 2005-10-19 | Conception et Développement Michelin S.A. | Imprégnation en continu de fibres en grandes longueurs, par de la résine, pour la fabrication d'éléments composites longilignes |
| US20030082385A1 (en) * | 2001-07-13 | 2003-05-01 | Toray Composites (America), Inc. | Quick cure carbon fiber reinforced epoxy resin |
| JP4177041B2 (ja) | 2002-07-18 | 2008-11-05 | 三菱レイヨン株式会社 | 繊維強化複合材料の製造方法 |
| ES2302980T5 (es) * | 2002-11-28 | 2015-12-01 | Mitsubishi Rayon Co., Ltd. | Procedimientos para la producción de material compuesto reforzado con fibras |
| US7208228B2 (en) * | 2003-04-23 | 2007-04-24 | Toray Composites (America), Inc. | Epoxy resin for fiber reinforced composite materials |
| US20050095415A1 (en) * | 2003-10-30 | 2005-05-05 | Raghavendran Venkat K. | Glass mat thermoplastic composite |
| JP2006028274A (ja) | 2004-07-14 | 2006-02-02 | Tokai Rubber Ind Ltd | エポキシ樹脂組成物およびこれを用いたプリプレグ |
| JP5090701B2 (ja) | 2006-09-30 | 2012-12-05 | 東邦テナックス株式会社 | 部分含浸プリプレグとそれを用いた繊維強化複合材料の製造方法 |
| JP2009292976A (ja) * | 2008-06-06 | 2009-12-17 | Mitsubishi Rayon Co Ltd | プレス成形用プリプレグ及び成形品の製造方法 |
| EP2314642B1 (en) * | 2008-07-31 | 2014-09-24 | Toray Industries, Inc. | Prepreg, preform, molded product, and method for manufacturing prepreg |
| JP5326435B2 (ja) * | 2008-08-29 | 2013-10-30 | 東レ株式会社 | エポキシ樹脂組成物、プリプレグ、および、繊維強化複合材料、ならびに、繊維強化複合材料の製造方法 |
| JP5668329B2 (ja) * | 2009-06-08 | 2015-02-12 | 三菱レイヨン株式会社 | エポキシ樹脂組成物およびそれを用いた繊維強化複合材料 |
-
2011
- 2011-11-07 TW TW100140457A patent/TW201229084A/zh unknown
- 2011-11-07 WO PCT/US2011/059610 patent/WO2012064662A1/en not_active Ceased
- 2011-11-07 RU RU2013126414/05A patent/RU2013126414A/ru not_active Application Discontinuation
- 2011-11-07 US US13/881,790 patent/US9957387B2/en active Active
- 2011-11-07 BR BR112013009345A patent/BR112013009345A2/pt not_active IP Right Cessation
- 2011-11-07 CN CN201180053710.5A patent/CN103201102B/zh active Active
- 2011-11-07 CA CA 2810709 patent/CA2810709A1/en not_active Abandoned
- 2011-11-07 EP EP11839752.0A patent/EP2637860B1/en active Active
- 2011-11-07 KR KR1020137010415A patent/KR101825247B1/ko active Active
- 2011-11-07 JP JP2013537913A patent/JP6007914B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| EP2637860B1 (en) | 2017-08-16 |
| US20130217283A1 (en) | 2013-08-22 |
| JP6007914B2 (ja) | 2016-10-19 |
| WO2012064662A1 (en) | 2012-05-18 |
| BR112013009345A2 (pt) | 2015-04-22 |
| JP2013543035A (ja) | 2013-11-28 |
| US9957387B2 (en) | 2018-05-01 |
| KR101825247B1 (ko) | 2018-02-02 |
| EP2637860A1 (en) | 2013-09-18 |
| TW201229084A (en) | 2012-07-16 |
| CN103201102B (zh) | 2015-07-01 |
| KR20130141491A (ko) | 2013-12-26 |
| CN103201102A (zh) | 2013-07-10 |
| RU2013126414A (ru) | 2014-12-20 |
| EP2637860A4 (en) | 2014-09-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2637860B1 (en) | Epoxy resin composition for fiber reinforced composite material, prepreg, and fiber reinforced composite material | |
| KR101951058B1 (ko) | 프리프레그, 섬유 강화 복합 재료 및 섬유 강화 복합 재료의 제조 방법 | |
| CN102498173B (zh) | 粘合剂组合物、增强纤维基材、预成型体及纤维增强复合材料及其制造方法 | |
| JP5469086B2 (ja) | 熱硬化性樹脂組成物とそれを用いたプリプレグ | |
| EP2794735B1 (en) | Improvements in or relating to fibre reinforced composites | |
| CA3020078C (en) | Prepreg and production method therefor | |
| RU2736820C2 (ru) | Композиция эпоксидной смолы, препрег и композитный материал, армированный углеродным волокном | |
| RU2712217C2 (ru) | Композиция эпоксидной смолы, препрег и армированный волокном композиционный материал | |
| JP5723505B2 (ja) | 樹脂組成物、硬化物、プリプレグ、および繊維強化複合材料 | |
| US20220153923A1 (en) | Thermosetting resin composition, prepreg, fiber-reinforced plastic molded body and method for producing same | |
| KR20160127023A (ko) | 에폭시 수지 조성물, 수지 경화물, 섬유 강화 복합 재료 및 프리프레그 | |
| WO2001027190A1 (en) | Epoxy resin composition for fiber-reinforced composite material, prepreg, and fiber-reinforced composite material | |
| KR20140127868A (ko) | 섬유강화 복합 재료 | |
| CN102834440A (zh) | 预浸料坯、纤维增强复合材料及预浸料坯的制造方法 | |
| KR20140127869A (ko) | 섬유강화 복합 재료 | |
| KR20140127867A (ko) | 섬유강화 복합 재료 | |
| EP3613788A1 (en) | Epoxy resin composition, prepreg, and carbon fiber-reinforced composite material | |
| KR20200125579A (ko) | 열경화성 수지 조성물, 프리프레그 및 섬유 강화 복합재료 | |
| WO2022163611A1 (ja) | エポキシ樹脂組成物、繊維強化複合材料およびその製造方法 | |
| JP2021516705A (ja) | プリプレグ、積層体、繊維強化複合材料、及び繊維強化複合材料の製造方法 | |
| CN104583284B (zh) | 纤维增强复合材料 | |
| WO2020040200A1 (ja) | プリプレグ | |
| JP4655329B2 (ja) | 一方向プリプレグおよび繊維強化複合材料 | |
| JP2011016985A (ja) | エポキシ樹脂組成物およびそれを用いた繊維強化複合材料 | |
| JP2009068000A (ja) | エポキシ樹脂組成物およびプリプレグ |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20171107 |