CA2230872A1 - Epoxy resin compositions, prepregs, cured composites, and methods of making the same - Google Patents
Epoxy resin compositions, prepregs, cured composites, and methods of making the same Download PDFInfo
- Publication number
- CA2230872A1 CA2230872A1 CA 2230872 CA2230872A CA2230872A1 CA 2230872 A1 CA2230872 A1 CA 2230872A1 CA 2230872 CA2230872 CA 2230872 CA 2230872 A CA2230872 A CA 2230872A CA 2230872 A1 CA2230872 A1 CA 2230872A1
- Authority
- CA
- Canada
- Prior art keywords
- fluorene
- amine curative
- fluorene amine
- epoxy resin
- cured
- 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 120
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 50
- 239000000203 mixture Substances 0.000 title claims abstract description 49
- 239000002131 composite material Substances 0.000 title claims abstract description 32
- 238000000034 method Methods 0.000 title description 20
- 229920005989 resin Polymers 0.000 claims abstract description 92
- 239000011347 resin Substances 0.000 claims abstract description 90
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 claims abstract description 78
- 125000003118 aryl group Chemical group 0.000 claims abstract description 48
- 239000007787 solid Substances 0.000 claims abstract description 17
- 230000009477 glass transition Effects 0.000 claims abstract description 8
- 239000000835 fiber Substances 0.000 claims description 43
- 230000002787 reinforcement Effects 0.000 claims description 20
- 239000011159 matrix material Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 230000005012 migration Effects 0.000 abstract description 9
- 238000013508 migration Methods 0.000 abstract description 9
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 30
- 239000003795 chemical substances by application Substances 0.000 description 17
- 238000012546 transfer Methods 0.000 description 16
- 239000011342 resin composition Substances 0.000 description 14
- 239000000843 powder Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 150000002500 ions Chemical class 0.000 description 9
- -1 curatives Substances 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000002671 adjuvant Substances 0.000 description 7
- 229920000049 Carbon (fiber) Polymers 0.000 description 6
- 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 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 6
- 239000004809 Teflon Substances 0.000 description 5
- 229920006362 Teflon® Polymers 0.000 description 5
- 230000032683 aging Effects 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003860 storage Methods 0.000 description 5
- 230000035882 stress Effects 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000282320 Panthera leo Species 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000002841 Lewis acid Substances 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 3
- 239000004917 carbon fiber Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007799 cork Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 229940052303 ethers for general anesthesia Drugs 0.000 description 3
- 238000009787 hand lay-up Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 150000007517 lewis acids Chemical class 0.000 description 3
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- 239000004416 thermosoftening plastic Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000003733 fiber-reinforced composite Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000010944 pre-mature reactiony Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 230000007480 spreading Effects 0.000 description 2
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- 239000004753 textile Substances 0.000 description 2
- 238000001721 transfer moulding Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 238000004804 winding Methods 0.000 description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- ZCLIABJNNBEIBM-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)-n-(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CNC1=CC=CC=C1OCC1CO1 ZCLIABJNNBEIBM-UHFFFAOYSA-N 0.000 description 1
- QDMXRSFKPPVBDW-UHFFFAOYSA-N 2-[9-(2-aminophenyl)fluoren-9-yl]aniline Chemical compound NC1=CC=CC=C1C1(C=2C(=CC=CC=2)N)C2=CC=CC=C2C2=CC=CC=C21 QDMXRSFKPPVBDW-UHFFFAOYSA-N 0.000 description 1
- NNBSNXYUIBPPBI-UHFFFAOYSA-N 2-chloro-4-[9-[3-chloro-4-(methylamino)phenyl]fluoren-9-yl]-n-methylaniline Chemical compound C1=C(Cl)C(NC)=CC=C1C1(C=2C=C(Cl)C(NC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 NNBSNXYUIBPPBI-UHFFFAOYSA-N 0.000 description 1
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 1
- SHTGJTMLIOIKKT-UHFFFAOYSA-N 4-[4-chloro-9-[4-(methylamino)phenyl]fluoren-9-yl]-n-methylaniline Chemical compound C1=CC(NC)=CC=C1C1(C=2C=CC(NC)=CC=2)C(C=CC=C2Cl)=C2C2=CC=CC=C21 SHTGJTMLIOIKKT-UHFFFAOYSA-N 0.000 description 1
- LRQNMTUEZUJDMA-UHFFFAOYSA-N 4-[9-(4-amino-3,5-dimethylphenyl)fluoren-9-yl]-2,6-dimethylaniline Chemical compound CC1=C(N)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(N)=C(C)C=2)=C1 LRQNMTUEZUJDMA-UHFFFAOYSA-N 0.000 description 1
- CIZUMWWHWPJAAK-UHFFFAOYSA-N 4-[9-(4-amino-3-chlorophenyl)fluoren-9-yl]-2-chloroaniline Chemical compound C1=C(Cl)C(N)=CC=C1C1(C=2C=C(Cl)C(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 CIZUMWWHWPJAAK-UHFFFAOYSA-N 0.000 description 1
- KDYWXMLVTFANGF-UHFFFAOYSA-N 4-[9-(4-amino-3-ethylphenyl)fluoren-9-yl]-2-ethylaniline Chemical compound C1=C(N)C(CC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(CC)C(N)=CC=2)=C1 KDYWXMLVTFANGF-UHFFFAOYSA-N 0.000 description 1
- VASAPMVFYCWJAC-UHFFFAOYSA-N 4-[9-(4-amino-3-methylphenyl)fluoren-9-yl]-2,6-diethylaniline Chemical compound CCC1=C(N)C(CC)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(N)=CC=2)=C1 VASAPMVFYCWJAC-UHFFFAOYSA-N 0.000 description 1
- YRKVLGUIGNRYJX-UHFFFAOYSA-N 4-[9-(4-amino-3-methylphenyl)fluoren-9-yl]-2-methylaniline Chemical compound C1=C(N)C(C)=CC(C2(C3=CC=CC=C3C3=CC=CC=C32)C=2C=C(C)C(N)=CC=2)=C1 YRKVLGUIGNRYJX-UHFFFAOYSA-N 0.000 description 1
- AMRHANGJBYPGKE-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-2,7-dinitrofluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC([N+]([O-])=O)=CC=C2C2=CC=C([N+]([O-])=O)C=C21 AMRHANGJBYPGKE-UHFFFAOYSA-N 0.000 description 1
- PBZLWMSBVHQLHN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-2-ethylfluoren-9-yl]aniline Chemical compound C12=CC(CC)=CC=C2C2=CC=CC=C2C1(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 PBZLWMSBVHQLHN-UHFFFAOYSA-N 0.000 description 1
- JOISDWWDEXYHCG-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-2-fluorofluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC(F)=CC=C2C2=CC=CC=C21 JOISDWWDEXYHCG-UHFFFAOYSA-N 0.000 description 1
- PHXKKHVBLDSVKR-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-4-chlorofluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C(C=CC=C2Cl)=C2C2=CC=CC=C21 PHXKKHVBLDSVKR-UHFFFAOYSA-N 0.000 description 1
- PJBLZPUJWNTDPL-UHFFFAOYSA-N 4-[9-(4-aminophenyl)-4-methylfluoren-9-yl]aniline Chemical compound CC1=CC=CC2=C1C1=CC=CC=C1C2(C=1C=CC(N)=CC=1)C1=CC=C(N)C=C1 PJBLZPUJWNTDPL-UHFFFAOYSA-N 0.000 description 1
- KIFDSGGWDIVQGN-UHFFFAOYSA-N 4-[9-(4-aminophenyl)fluoren-9-yl]aniline Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 KIFDSGGWDIVQGN-UHFFFAOYSA-N 0.000 description 1
- QFWYKFPCIFDQHB-UHFFFAOYSA-N 4-[9-[3,5-dimethyl-4-(methylamino)phenyl]fluoren-9-yl]-n,2,6-trimethylaniline Chemical compound C1=C(C)C(NC)=C(C)C=C1C1(C=2C=C(C)C(NC)=C(C)C=2)C2=CC=CC=C2C2=CC=CC=C21 QFWYKFPCIFDQHB-UHFFFAOYSA-N 0.000 description 1
- WRIQVHHYPAKIFD-UHFFFAOYSA-N 4-[9-[4-(ethylamino)phenyl]fluoren-9-yl]-n-methylaniline Chemical compound C1=CC(NCC)=CC=C1C1(C=2C=CC(NC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 WRIQVHHYPAKIFD-UHFFFAOYSA-N 0.000 description 1
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- YFONKFDEZLYQDH-OPQQBVKSSA-N N-[(1R,2S)-2,6-dimethyindan-1-yl]-6-[(1R)-1-fluoroethyl]-1,3,5-triazine-2,4-diamine Chemical compound C[C@@H](F)C1=NC(N)=NC(N[C@H]2C3=CC(C)=CC=C3C[C@@H]2C)=N1 YFONKFDEZLYQDH-OPQQBVKSSA-N 0.000 description 1
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- DPNISTOAESHQJF-UHFFFAOYSA-N n-methyl-4-[2-methyl-9-[4-(methylamino)phenyl]fluoren-9-yl]aniline Chemical compound C1=CC(NC)=CC=C1C1(C=2C=CC(NC)=CC=2)C2=CC(C)=CC=C2C2=CC=CC=C21 DPNISTOAESHQJF-UHFFFAOYSA-N 0.000 description 1
- WINGACDUUPIWFZ-UHFFFAOYSA-N n-methyl-4-[9-[4-(methylamino)phenyl]fluoren-9-yl]aniline Chemical compound C1=CC(NC)=CC=C1C1(C=2C=CC(NC)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 WINGACDUUPIWFZ-UHFFFAOYSA-N 0.000 description 1
- OJVIJGVKJMPVAE-UHFFFAOYSA-N n-propan-2-yl-4-[9-[4-(propan-2-ylamino)phenyl]fluoren-9-yl]aniline Chemical compound C1=CC(NC(C)C)=CC=C1C1(C=2C=CC(NC(C)C)=CC=2)C2=CC=CC=C2C2=CC=CC=C21 OJVIJGVKJMPVAE-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001230 polyarylate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012783 reinforcing fiber Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/20—Compounding polymers with additives, e.g. colouring
- C08J3/201—Pre-melted polymers
-
- 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
-
- 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
- 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
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/30—Self-sustaining carbon mass or layer with impregnant or other layer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Inorganic Chemistry (AREA)
- Reinforced Plastic Materials (AREA)
- Epoxy Resins (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/532941 | 1995-09-22 | ||
| US08/532,941 US5728755A (en) | 1995-09-22 | 1995-09-22 | Curable epoxy resin compositions with 9,9'-bis(4-aminophenyl)fluorenes as curatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2230872A1 true CA2230872A1 (en) | 1997-03-27 |
Family
ID=24123838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2230872 Abandoned CA2230872A1 (en) | 1995-09-22 | 1996-07-29 | Epoxy resin compositions, prepregs, cured composites, and methods of making the same |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US5728755A (enExample) |
| EP (1) | EP0851887B1 (enExample) |
| JP (1) | JP3864210B2 (enExample) |
| KR (1) | KR19990063620A (enExample) |
| AU (1) | AU6603896A (enExample) |
| CA (1) | CA2230872A1 (enExample) |
| DE (1) | DE69627675T2 (enExample) |
| IL (1) | IL123452A0 (enExample) |
| WO (1) | WO1997011112A1 (enExample) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2748486B1 (fr) * | 1996-05-09 | 1998-06-19 | Inst Francais Du Petrole | Compositions thermodurcissables a latence amelioree a base de polyamine aromatique primaire, en suspension dans une resine epoxy et utilisation pour l'impregnation de preformes |
| FR2753978B1 (fr) * | 1996-09-30 | 1999-05-14 | Inst Francais Du Petrole | Composition thermodurcissable, ses utilisations et preforme souple depliable comprenant cette composition |
| US6506325B1 (en) * | 1999-02-05 | 2003-01-14 | The B. F. Goodrich Company | Method controlling the exotherm of a vacuum resin infusion |
| US6537483B1 (en) * | 1999-02-05 | 2003-03-25 | The B. F. Goodrich Company | Pressure equalized vacuum resin infusion process |
| 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 |
| US7141303B2 (en) * | 2001-03-06 | 2006-11-28 | 3M Innovative Properties Company | Protective articles |
| US7070850B2 (en) * | 2002-12-31 | 2006-07-04 | 3M Innovative Properties Company | Drag reduction article and method of use |
| US7044324B2 (en) * | 2003-10-24 | 2006-05-16 | United Technologies Corporation | Composite material |
| US8029889B1 (en) | 2004-12-03 | 2011-10-04 | Henkel Corporation | Prepregs, towpregs and preforms |
| US7649060B2 (en) * | 2005-12-02 | 2010-01-19 | Henkel Corporation | Curable compositions |
| JP2006245453A (ja) * | 2005-03-07 | 2006-09-14 | Three M Innovative Properties Co | フレキシブルプリント回路基板の他の回路基板への接続方法 |
| US8772398B2 (en) * | 2005-09-28 | 2014-07-08 | Entrotech Composites, Llc | Linerless prepregs, composite articles therefrom, and related methods |
| US10449736B2 (en) | 2006-02-02 | 2019-10-22 | The Boeing Company | Apparatus for fabricating thermoplastic composite parts |
| US7807005B2 (en) * | 2006-02-02 | 2010-10-05 | The Boeing Company | Fabrication process for thermoplastic composite parts |
| US9102103B2 (en) * | 2006-02-02 | 2015-08-11 | The Boeing Company | Thermoplastic composite parts having integrated metal fittings and method of making the same |
| US8333858B2 (en) * | 2006-02-02 | 2012-12-18 | The Boeing Company | Method for fabricating curved thermoplastic composite parts |
| US8491745B2 (en) | 2007-02-03 | 2013-07-23 | The Boeing Company | Method and material efficient tooling for continuous compression molding |
| US8691137B2 (en) * | 2009-03-04 | 2014-04-08 | The Boeing Company | Method of molding partus using a tool sleeve for mold die |
| US10232532B1 (en) | 2006-02-02 | 2019-03-19 | The Boeing Company | Method for fabricating tapered thermoplastic composite parts |
| JP4969363B2 (ja) | 2006-08-07 | 2012-07-04 | 東レ株式会社 | プリプレグおよび炭素繊維強化複合材料 |
| US20080078876A1 (en) * | 2006-08-15 | 2008-04-03 | Baggette Phillip D | Composite resin window frame constructions for airplanes |
| US8449709B2 (en) * | 2007-05-25 | 2013-05-28 | The Boeing Company | Method of fabricating fiber reinforced composite structure having stepped surface |
| US20110052874A1 (en) * | 2009-07-02 | 2011-03-03 | Wensheng Zhou | Roofing articles with highly reflective coated granules |
| WO2011082374A1 (en) | 2009-12-31 | 2011-07-07 | Firestone Building Products Company, Llc | Asphaltic membrane with mullite-containing granules |
| US10821653B2 (en) * | 2010-02-24 | 2020-11-03 | Alexander M. Rubin | Continuous molding of thermoplastic laminates |
| GB201009851D0 (en) * | 2010-06-14 | 2010-07-21 | Hexcel Composites Ltd | Improvements in composite materials |
| CA2837862C (en) * | 2011-06-03 | 2018-10-23 | Cytec Technology Corp. | Resin coated radius fillers and system and method of making the same |
| TWI549923B (zh) * | 2011-06-27 | 2016-09-21 | 台燿科技股份有限公司 | 熔合填料及其製法與應用 |
| CN102850720B (zh) * | 2011-07-01 | 2015-07-22 | 台燿科技股份有限公司 | 熔合填料及其制法与应用 |
| US8826957B2 (en) * | 2012-08-31 | 2014-09-09 | General Electric Company | Methods and systems for automated ply layup for composites |
| DE102013214419A1 (de) * | 2013-07-24 | 2015-01-29 | Sgl Carbon Se | Tooling Prepreg mit hoher Lagerbeständigkeit und Verfahren zu dessen Herstellung |
| GB201421373D0 (en) | 2014-12-02 | 2015-01-14 | Cytec Ind Inc | Modified amine curing agents, their preparation and use in curable compositions |
| GB2533776B (en) * | 2014-12-23 | 2020-11-04 | Hexcel Composites Ltd | Resin Composition |
| US11078358B2 (en) | 2017-07-31 | 2021-08-03 | 3M Innovative Properties Company | Curable composition including epoxy resin and curable solid filler |
| ES2944118T3 (es) * | 2017-12-21 | 2023-06-19 | Huntsman Advanced Mat Americas Llc | Sistema epoxi curable |
| WO2020008847A1 (ja) | 2018-07-06 | 2020-01-09 | 東レ株式会社 | 繊維強化複合材料用エポキシ樹脂組成物、および繊維強化複合材料ならびにその製造方法 |
| WO2022176773A1 (ja) | 2021-02-18 | 2022-08-25 | 東レ株式会社 | 繊維強化複合材料用エポキシ樹脂組成物、繊維強化複合材料、および繊維強化複合材料の製造方法 |
| CN113549169B (zh) * | 2021-06-15 | 2022-12-06 | 南京工业大学 | 一种苯基芴胺类聚合物空穴传输材料及其制备方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1595807B2 (de) * | 1966-08-18 | 1977-03-10 | Henkel & Cie GmbH, 4000 Düsseldorf | Verfahren zur herstellung von pressmassen auf basis von mehr als eine epoxidgruppe im molekuel enthaltenden verbindungen |
| US3825506A (en) * | 1972-01-26 | 1974-07-23 | Glasrock Products | Method of preparation of a porous thermosetting resin |
| US4684678A (en) * | 1985-05-30 | 1987-08-04 | Minnesota Mining And Manufacturing Company | Epoxy resin curing agent, process, and composition |
| CA1264476A (en) * | 1985-05-30 | 1990-01-16 | William J. Schultz | Epoxy resin curing agent, process, and composition |
| US4769399A (en) * | 1987-03-12 | 1988-09-06 | Minnesota Mining And Manufacturing Company | Epoxy adhesive film for electronic applications |
| US4882370A (en) * | 1988-01-27 | 1989-11-21 | Minnesota Mining And Manufacturing Company | Fiber reinforced composites with improved glass transition temperatures |
| EP0441047B1 (en) * | 1990-01-19 | 1996-06-05 | Minnesota Mining And Manufacturing Company | Thermosettable composition |
| CA2034969A1 (en) * | 1990-02-09 | 1991-08-10 | Walter V. Breitigam | Process for preparing thermoset composite articles |
| US5369192A (en) * | 1993-06-28 | 1994-11-29 | Minnesota Mining And Manufacturing Company | Binder resin for resin transfer molding preforms |
| US5541000A (en) * | 1993-08-17 | 1996-07-30 | Minnesota Mining And Manufacturing Company | Latent, thermal cure accelerators for epoxy-aromatic amine resins having lowered peak exotherms |
| US5648407A (en) * | 1995-05-16 | 1997-07-15 | Minnesota Mining And Manufacturing Company | Curable resin sols and fiber-reinforced composites derived therefrom |
-
1995
- 1995-09-22 US US08/532,941 patent/US5728755A/en not_active Expired - Lifetime
-
1996
- 1996-07-29 DE DE1996627675 patent/DE69627675T2/de not_active Expired - Lifetime
- 1996-07-29 EP EP19960925563 patent/EP0851887B1/en not_active Expired - Lifetime
- 1996-07-29 KR KR1019980702068A patent/KR19990063620A/ko not_active Withdrawn
- 1996-07-29 CA CA 2230872 patent/CA2230872A1/en not_active Abandoned
- 1996-07-29 JP JP51268297A patent/JP3864210B2/ja not_active Expired - Lifetime
- 1996-07-29 WO PCT/US1996/012427 patent/WO1997011112A1/en not_active Ceased
- 1996-07-29 AU AU66038/96A patent/AU6603896A/en not_active Abandoned
- 1996-07-29 IL IL12345296A patent/IL123452A0/xx unknown
-
1997
- 1997-12-22 US US08/995,299 patent/US6007917A/en not_active Expired - Lifetime
-
1999
- 1999-10-15 US US09/418,913 patent/US6054221A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP0851887B1 (en) | 2003-04-23 |
| JP3864210B2 (ja) | 2006-12-27 |
| US6054221A (en) | 2000-04-25 |
| KR19990063620A (ko) | 1999-07-26 |
| JPH11511503A (ja) | 1999-10-05 |
| US5728755A (en) | 1998-03-17 |
| AU6603896A (en) | 1997-04-09 |
| WO1997011112A1 (en) | 1997-03-27 |
| DE69627675T2 (de) | 2004-04-08 |
| DE69627675D1 (de) | 2003-05-28 |
| EP0851887A1 (en) | 1998-07-08 |
| US6007917A (en) | 1999-12-28 |
| IL123452A0 (en) | 1998-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |