CA1322948C - Composes resistants contenant des particules infusibles - Google Patents

Composes resistants contenant des particules infusibles

Info

Publication number: CA1322948C
Authority: CA; Canada
Prior art keywords: epoxy resin; particles; matrix; composite; filaments
Prior art date: 1986-07-09
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.): Expired - Lifetime

Application number

CA000616093A

Other languages

English (en)

Inventor

Irena Gawin

Brian Joseph Swetlin

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hercules LLC

Original Assignee

Hercules LLC

Priority date (The priority date 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 date listed.)

1986-07-09

Filing date

1991-06-14

Publication date

1993-10-12

1986-07-09 Priority claimed from US06/884,139 external-priority patent/US4863787A/en

1991-06-14 Application filed by Hercules LLC filed Critical Hercules LLC

1991-06-14 Priority to CA000616093A priority Critical patent/CA1322948C/fr

1993-10-12 Application granted granted Critical

1993-10-12 Publication of CA1322948C publication Critical patent/CA1322948C/fr

2007-06-25 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

239000002245 particle Substances 0.000 title claims abstract description 119
239000002131 composite material Substances 0.000 title claims abstract description 87
229920000647 polyepoxide Polymers 0.000 claims abstract description 129
239000003822 epoxy resin Substances 0.000 claims abstract description 110
239000011159 matrix material Substances 0.000 claims abstract description 44
229920000642 polymer Polymers 0.000 claims description 42
229920001971 elastomer Polymers 0.000 claims description 41
239000005060 rubber Substances 0.000 claims description 40
239000011521 glass Substances 0.000 claims description 6
239000000919 ceramic Substances 0.000 claims description 5
239000000203 mixture Substances 0.000 abstract description 101
229920005989 resin Polymers 0.000 abstract description 57
239000011347 resin Substances 0.000 abstract description 57
238000000034 method Methods 0.000 abstract description 37
239000000835 fiber Substances 0.000 abstract description 12
230000008569 process Effects 0.000 abstract description 6
239000002344 surface layer Substances 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 description 27
229920000049 Carbon (fiber) Polymers 0.000 description 25
239000004917 carbon fiber Substances 0.000 description 25
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 22
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 21
150000002118 epoxides Chemical group 0.000 description 21
150000001412 amines Chemical class 0.000 description 18
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 15
239000002904 solvent Substances 0.000 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 description 14
150000001875 compounds Chemical class 0.000 description 14
238000002156 mixing Methods 0.000 description 14
239000000047 product Substances 0.000 description 14
239000004593 Epoxy Substances 0.000 description 13
239000004695 Polyether sulfone Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 12
-1 epoxide compound Chemical class 0.000 description 12
229920006393 polyether sulfone Polymers 0.000 description 12
238000007906 compression Methods 0.000 description 11
230000006835 compression Effects 0.000 description 11
238000010438 heat treatment Methods 0.000 description 11
229920000412 polyarylene Polymers 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
238000012545 processing Methods 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 9
239000010408 film Substances 0.000 description 8
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 8
239000004848 polyfunctional curative Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
229920000459 Nitrile rubber Polymers 0.000 description 7
NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 7
229940032007 methylethyl ketone Drugs 0.000 description 7
238000001000 micrograph Methods 0.000 description 7
ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical compound C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 6
125000002947 alkylene group Chemical group 0.000 description 6
239000003963 antioxidant agent Substances 0.000 description 6
230000003078 antioxidant effect Effects 0.000 description 6
229940106691 bisphenol a Drugs 0.000 description 6
230000009477 glass transition Effects 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
239000000463 material Substances 0.000 description 6
150000003457 sulfones Chemical class 0.000 description 6
238000012360 testing method Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
229920001169 thermoplastic Polymers 0.000 description 6
239000004416 thermosoftening plastic Substances 0.000 description 6
PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
238000009826 distribution Methods 0.000 description 5
238000009472 formulation Methods 0.000 description 5
229920002492 poly(sulfone) Polymers 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000011342 resin composition Substances 0.000 description 5
229920001187 thermosetting polymer Polymers 0.000 description 5
239000003039 volatile agent Substances 0.000 description 5
CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 4
CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 4
AHIPJALLQVEEQF-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=C1)=CC=C1N(CC1OC1)CC1CO1 AHIPJALLQVEEQF-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
229920013646 Hycar Polymers 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
238000013459 approach Methods 0.000 description 4
150000004984 aromatic diamines Chemical class 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000012141 concentrate Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
238000005191 phase separation Methods 0.000 description 4
229920000570 polyether Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000002002 slurry Substances 0.000 description 4
229910052717 sulfur Inorganic materials 0.000 description 4
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
PULOARGYCVHSDH-UHFFFAOYSA-N 2-amino-3,4,5-tris(oxiran-2-ylmethyl)phenol Chemical compound C1OC1CC1=C(CC2OC2)C(N)=C(O)C=C1CC1CO1 PULOARGYCVHSDH-UHFFFAOYSA-N 0.000 description 3
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 3
239000004721 Polyphenylene oxide Substances 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
229920001079 Thiokol (polymer) Polymers 0.000 description 3
229910000288 alkali metal carbonate Inorganic materials 0.000 description 3
150000008041 alkali metal carbonates Chemical class 0.000 description 3
125000001118 alkylidene group Chemical group 0.000 description 3
150000001491 aromatic compounds Chemical class 0.000 description 3
239000011324 bead Substances 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 3
238000004090 dissolution Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
238000011065 in-situ storage Methods 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
230000001788 irregular Effects 0.000 description 3
OANVFVBYPNXRLD-UHFFFAOYSA-M propyromazine bromide Chemical compound [Br-].C12=CC=CC=C2SC2=CC=CC=C2N1C(=O)C(C)[N+]1(C)CCCC1 OANVFVBYPNXRLD-UHFFFAOYSA-M 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
IBRQUKZZBXZOBA-UHFFFAOYSA-N 1-chloro-3-(3-chlorophenyl)sulfonylbenzene Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C=C(Cl)C=CC=2)=C1 IBRQUKZZBXZOBA-UHFFFAOYSA-N 0.000 description 2
UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 2
FAUAZXVRLVIARB-UHFFFAOYSA-N 4-[[4-[bis(oxiran-2-ylmethyl)amino]phenyl]methyl]-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1CN(C=1C=CC(CC=2C=CC(=CC=2)N(CC2OC2)CC2OC2)=CC=1)CC1CO1 FAUAZXVRLVIARB-UHFFFAOYSA-N 0.000 description 2
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
101100379068 Caenorhabditis elegans apc-2 gene Proteins 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
238000005054 agglomeration Methods 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000009835 boiling Methods 0.000 description 2
IRLQAJPIHBZROB-UHFFFAOYSA-N buta-2,3-dienenitrile Chemical compound C=C=CC#N IRLQAJPIHBZROB-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
238000012669 compression test Methods 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical group C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
SLAFUPJSGFVWPP-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;iodide Chemical compound [I-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 SLAFUPJSGFVWPP-UHFFFAOYSA-M 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910002804 graphite Inorganic materials 0.000 description 2
239000010439 graphite Substances 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
229920003052 natural elastomer Polymers 0.000 description 2
229920001194 natural rubber Polymers 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
125000005702 oxyalkylene group Chemical group 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
229920002490 poly(thioether-sulfone) polymer Polymers 0.000 description 2
238000003825 pressing Methods 0.000 description 2
150000003141 primary amines Chemical class 0.000 description 2
150000003335 secondary amines Chemical class 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FBOUIAKEJMZPQG-AWNIVKPZSA-N (1E)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol Chemical compound C1=NC=NN1/C(C(O)C(C)(C)C)=C/C1=CC=C(Cl)C=C1Cl FBOUIAKEJMZPQG-AWNIVKPZSA-N 0.000 description 1
FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 1
VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 description 1
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
GFPCHXLNBRGOSJ-UHFFFAOYSA-N 2-[[2-bromo-4-[2-[3-bromo-4-(oxiran-2-ylmethoxy)phenyl]propan-2-yl]phenoxy]methyl]oxirane Chemical compound C=1C=C(OCC2OC2)C(Br)=CC=1C(C)(C)C(C=C1Br)=CC=C1OCC1CO1 GFPCHXLNBRGOSJ-UHFFFAOYSA-N 0.000 description 1
JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
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 description 1
VAGOJLCWTUPBKD-UHFFFAOYSA-N 3-(oxiran-2-ylmethoxy)-n,n-bis(oxiran-2-ylmethyl)aniline Chemical compound C1OC1COC(C=1)=CC=CC=1N(CC1OC1)CC1CO1 VAGOJLCWTUPBKD-UHFFFAOYSA-N 0.000 description 1
229940018563 3-aminophenol Drugs 0.000 description 1
ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 1
GPAPPPVRLPGFEQ-UHFFFAOYSA-N 4,4'-dichlorodiphenyl sulfone Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 GPAPPPVRLPGFEQ-UHFFFAOYSA-N 0.000 description 1
KOGSPLLRMRSADR-UHFFFAOYSA-N 4-(2-aminopropan-2-yl)-1-methylcyclohexan-1-amine Chemical compound CC(C)(N)C1CCC(C)(N)CC1 KOGSPLLRMRSADR-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
FVCSARBUZVPSQF-UHFFFAOYSA-N 5-(2,4-dioxooxolan-3-yl)-7-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C(C(OC2=O)=O)C2C(C)=CC1C1C(=O)COC1=O FVCSARBUZVPSQF-UHFFFAOYSA-N 0.000 description 1
101150039167 Bex3 gene Proteins 0.000 description 1
229930185605 Bisphenol Natural products 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WPYCRFCQABTEKC-UHFFFAOYSA-N Diglycidyl resorcinol ether Chemical compound C1OC1COC(C=1)=CC=CC=1OCC1CO1 WPYCRFCQABTEKC-UHFFFAOYSA-N 0.000 description 1
YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
239000006057 Non-nutritive feed additive Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
229920000297 Rayon Polymers 0.000 description 1
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
241000534944 Thia Species 0.000 description 1
230000009471 action Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000003973 alkyl amines Chemical group 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
YKOQAAJBYBTSBS-UHFFFAOYSA-N biphenyl-2,3-diol Chemical class OC1=CC=CC(C=2C=CC=CC=2)=C1O YKOQAAJBYBTSBS-UHFFFAOYSA-N 0.000 description 1
239000004842 bisphenol F epoxy resin Substances 0.000 description 1
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical class FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
238000010000 carbonizing Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000000806 elastomer Substances 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
GELSOTNVVKOYAW-UHFFFAOYSA-N ethyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 GELSOTNVVKOYAW-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000009730 filament winding Methods 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229920001002 functional polymer Polymers 0.000 description 1
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
230000005484 gravity Effects 0.000 description 1
238000000227 grinding Methods 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229940018564 m-phenylenediamine Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
DFQICHCWIIJABH-UHFFFAOYSA-N naphthalene-2,7-diol Chemical compound C1=CC(O)=CC2=CC(O)=CC=C21 DFQICHCWIIJABH-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
150000004986 phenylenediamines Chemical class 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
229960004063 propylene glycol Drugs 0.000 description 1
VHNQIURBCCNWDN-UHFFFAOYSA-N pyridine-2,6-diamine Chemical compound NC1=CC=CC(N)=N1 VHNQIURBCCNWDN-UHFFFAOYSA-N 0.000 description 1
239000002964 rayon Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000000630 rising effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
229910052979 sodium sulfide Inorganic materials 0.000 description 1
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
229920003048 styrene butadiene rubber Polymers 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
229920005992 thermoplastic resin Polymers 0.000 description 1
239000010409 thin film Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

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CA000616093A 1986-07-09 1991-06-14 Composes resistants contenant des particules infusibles Expired - Lifetime CA1322948C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000616093A CA1322948C (fr)	1986-07-09	1991-06-14	Composes resistants contenant des particules infusibles

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US884,139		1986-07-09
US06/884,139 US4863787A (en)	1986-07-09	1986-07-09	Damage tolerant composites containing infusible particles
CA 540492 CA1300783C (fr)	1986-07-09	1987-06-25	Composites a tolerance aux avaries renfermant des particules non fusibles
CA000616093A CA1322948C (fr)	1986-07-09	1991-06-14	Composes resistants contenant des particules infusibles

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 540492 Division CA1300783C (fr)	1986-07-09	1987-06-25	Composites a tolerance aux avaries renfermant des particules non fusibles

Publications (1)

Publication Number	Publication Date
CA1322948C true CA1322948C (fr)	1993-10-12

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ID=25671393

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Application Number	Title	Priority Date	Filing Date
CA000616092A Expired - Lifetime CA1326176C (fr)	1986-07-09	1991-06-14	Composites resistants contenant des particules infusibles
CA000616093A Expired - Lifetime CA1322948C (fr)	1986-07-09	1991-06-14	Composes resistants contenant des particules infusibles

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
CA000616092A Expired - Lifetime CA1326176C (fr)	1986-07-09	1991-06-14	Composites resistants contenant des particules infusibles

Country Status (1)

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CA (2)	CA1326176C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20230242451A1 (en) *	2022-02-03	2023-08-03	General Electric Company	Tools and methods for their formation and use

1991
- 1991-06-14 CA CA000616092A patent/CA1326176C/fr not_active Expired - Lifetime
- 1991-06-14 CA CA000616093A patent/CA1322948C/fr not_active Expired - Lifetime

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20230242451A1 (en) *	2022-02-03	2023-08-03	General Electric Company	Tools and methods for their formation and use

Also Published As

Publication number	Publication date
CA1326176C (fr)	1994-01-18

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Date	Code	Title	Description
2010-10-12	MKEX	Expiry	Effective date: 20101012

Publication	Publication Date	Title
US4863787A (en)	1989-09-05	Damage tolerant composites containing infusible particles
US4783506A (en)	1988-11-08	Damage tolerant composites containing infusible particles
US4999238A (en)	1991-03-12	Damage tolerant composites containing infusible particles
US5025045A (en)	1991-06-18	Damage tolerant composites containing infusible particles
EP0193082B1 (fr)	1990-03-21	Compositions de résines d'époxydes thermodurcissables et produits thermodurcis préparés à partir de ces compositions
US5169710A (en)	1992-12-08	Fiber-reinforced composites toughened with porous resin particles
US5087657A (en)	1992-02-11	Fiber-reinforced composites toughened with resin particles
JPS642609B2 (fr)	1989-01-18
US4874661A (en)	1989-10-17	Impact enhanced prepregs and formulations
US5405688A (en)	1995-04-11	Epoxy resin/aminopolysiloxane/aromatic oligomer composite
EP2470367B1 (fr)	2019-01-09	Durcissement interlaminaire de particules thermoplastiques réticulées modifiées
EP0311349B1 (fr)	1996-09-11	Composition de polymères
US5268223A (en)	1993-12-07	Toughened fiber-reinforced composites
EP0259100A2 (fr)	1988-03-09	Epoxydes thermodurcissables polyphasés contenant du caoutchouc à l'intérieur de la phase dispersée
JPH0368650A (ja)	1991-03-25	強化熱硬化性構造材料
JPH10511426A (ja)	1998-11-04	硬化剤と強化剤とを含むエポキシ樹脂
EP0583224B1 (fr)	1999-01-20	Résines thermodurcissables endurcies par des polymères sulfones
US4822832A (en)	1989-04-18	Thermosetting epoxy resin compositions and thermosets therefrom
EP0486044A2 (fr)	1992-05-20	Matériau composite résistant à l'usure contenant des particules infusibles
US5231150A (en)	1993-07-27	Polymer composition
US4992325A (en)	1991-02-12	Inorganic whisker containing impact enhanced prepregs and formulations formulations
CA1322948C (fr)	1993-10-12	Composes resistants contenant des particules infusibles
US5002821A (en)	1991-03-26	Toughened prepregs and formulations
GB2257144A (en)	1993-01-06	Fibre-reinforced composites toughened with porous resin particles
JP2584452B2 (ja)	1997-02-26	不融性粒子を含有する耐衝撃性のコンポジット

CA1322948C - Composes resistants contenant des particules infusibles - Google Patents

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Priority Applications (1)

Applications Claiming Priority (4)

Related Parent Applications (1)

Publications (1)

Family

ID=25671393

Family Applications (2)

Family Applications Before (1)

Country Status (1)

Cited By (1)

Cited By (1)

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