CA2023864A1 - Matieres composites de resine thermoplastique/fibres de carbone a grande resistance - Google Patents

Matieres composites de resine thermoplastique/fibres de carbone a grande resistance

Info

Publication number: CA2023864A1
Authority: CA; Canada
Prior art keywords: resin; poly; amine; sulfide; carbon fiber
Prior art date: 1989-07-24
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

Application number

CA002023864A

Other languages

English (en)

Inventor

Rex L. Bobsein

Stuart D. Mills

Mark L. Stone

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.)

Phillips Petroleum Co

Original Assignee

Phillips Petroleum Co

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.)

1989-07-24

Filing date

1990-08-23

Publication date

1992-02-24

1989-07-24 Priority claimed from US07/383,751 external-priority patent/US5039572A/en

1990-08-23 Application filed by Phillips Petroleum Co filed Critical Phillips Petroleum Co

1990-08-23 Priority to CA002023864A priority Critical patent/CA2023864A1/fr

1992-02-24 Publication of CA2023864A1 publication Critical patent/CA2023864A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 57
229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 49
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 30
239000011347 resin Substances 0.000 claims abstract description 129
229920005989 resin Polymers 0.000 claims abstract description 129
-1 poly(arylene sulfide Chemical compound 0.000 claims abstract description 116
239000004917 carbon fiber Substances 0.000 claims abstract description 66
229920000049 Carbon (fiber) Polymers 0.000 claims abstract description 65
239000002131 composite material Substances 0.000 claims abstract description 62
239000000203 mixture Substances 0.000 claims abstract description 38
150000003457 sulfones Chemical class 0.000 claims abstract description 23
239000004977 Liquid-crystal polymers (LCPs) Substances 0.000 claims abstract description 8
239000004696 Poly ether ether ketone Substances 0.000 claims abstract description 8
229920002530 polyetherether ketone Polymers 0.000 claims abstract description 8
229920001643 poly(ether ketone) Polymers 0.000 claims abstract description 7
229920002492 poly(sulfone) Polymers 0.000 claims abstract description 7
229920000106 Liquid crystal polymer Polymers 0.000 claims abstract description 6
229920001652 poly(etherketoneketone) Polymers 0.000 claims abstract description 5
229920001601 polyetherimide Polymers 0.000 claims abstract description 5
229920000098 polyolefin Polymers 0.000 claims abstract description 5
239000000306 component Substances 0.000 claims description 57
125000000732 arylene group Chemical group 0.000 claims description 24
229920000069 polyphenylene sulfide Polymers 0.000 claims description 22
239000011159 matrix material Substances 0.000 claims description 18
UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 17
ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 claims description 14
239000000155 melt Substances 0.000 claims description 8
229920006393 polyether sulfone Polymers 0.000 claims description 7
150000003568 thioethers Chemical class 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 3
238000002156 mixing Methods 0.000 claims description 2
239000004721 Polyphenylene oxide Substances 0.000 abstract 1
239000000835 fiber Substances 0.000 description 17
238000004513 sizing Methods 0.000 description 17
229920000642 polymer Polymers 0.000 description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 12
229910052717 sulfur Inorganic materials 0.000 description 12
239000011593 sulfur Substances 0.000 description 12
238000006116 polymerization reaction Methods 0.000 description 11
239000004416 thermosoftening plastic Substances 0.000 description 10
150000001875 compounds Chemical class 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
150000001491 aromatic compounds Chemical class 0.000 description 8
229910052751 metal Inorganic materials 0.000 description 7
239000002184 metal Substances 0.000 description 7
229920001169 thermoplastic Polymers 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
150000002894 organic compounds Chemical class 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 5
239000004634 thermosetting polymer Substances 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
229920013632 Ryton Polymers 0.000 description 4
239000004736 Ryton® Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
238000005406 washing Methods 0.000 description 4
PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
239000012783 reinforcing fiber Substances 0.000 description 3
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 3
150000007944 thiolates Chemical class 0.000 description 3
SUDANDSURGYEPX-UHFFFAOYSA-N 2-aminobenzenethiol Chemical compound NC1=CC=CC=C1S.NC1=CC=CC=C1S SUDANDSURGYEPX-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
229910052977 alkali metal sulfide Inorganic materials 0.000 description 2
125000003118 aryl group Chemical class 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
230000006870 function Effects 0.000 description 2
239000003365 glass fiber Substances 0.000 description 2
150000002367 halogens Chemical group 0.000 description 2
125000005842 heteroatom Chemical group 0.000 description 2
238000001746 injection moulding Methods 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
150000002736 metal compounds Chemical class 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
CPRMKOQKXYSDML-UHFFFAOYSA-M rubidium hydroxide Chemical compound [OH-].[Rb+] CPRMKOQKXYSDML-UHFFFAOYSA-M 0.000 description 2
229940083608 sodium hydroxide Drugs 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
229910052979 sodium sulfide Inorganic materials 0.000 description 2
GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 2
IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
RCTKUIOMKBEGTG-UHFFFAOYSA-N 1,3,5-trichloro-2-methylbenzene Chemical compound CC1=C(Cl)C=C(Cl)C=C1Cl RCTKUIOMKBEGTG-UHFFFAOYSA-N 0.000 description 1
XKEFYDZQGKAQCN-UHFFFAOYSA-N 1,3,5-trichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Cl)=C1 XKEFYDZQGKAQCN-UHFFFAOYSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
ZPQOPVIELGIULI-UHFFFAOYSA-N 1,3-dichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1 ZPQOPVIELGIULI-UHFFFAOYSA-N 0.000 description 1
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
UTGSRNVBAFCOEU-UHFFFAOYSA-N 1,4-dichloro-2,5-dimethylbenzene Chemical group CC1=CC(Cl)=C(C)C=C1Cl UTGSRNVBAFCOEU-UHFFFAOYSA-N 0.000 description 1
KFAKZJUYBOYVKA-UHFFFAOYSA-N 1,4-dichloro-2-methylbenzene Chemical compound CC1=CC(Cl)=CC=C1Cl KFAKZJUYBOYVKA-UHFFFAOYSA-N 0.000 description 1
LFMWZTSOMGDDJU-UHFFFAOYSA-N 1,4-diiodobenzene Chemical compound IC1=CC=C(I)C=C1 LFMWZTSOMGDDJU-UHFFFAOYSA-N 0.000 description 1
NFTWWHSKWXOTLL-UHFFFAOYSA-N 1,4-dimethylpiperazin-2-one Chemical compound CN1CCN(C)C(=O)C1 NFTWWHSKWXOTLL-UHFFFAOYSA-N 0.000 description 1
ZFPGARUNNKGOBB-UHFFFAOYSA-N 1-Ethyl-2-pyrrolidinone Chemical compound CCN1CCCC1=O ZFPGARUNNKGOBB-UHFFFAOYSA-N 0.000 description 1
DZHFFMWJXJBBRG-UHFFFAOYSA-N 1-bromo-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(Br)=C1 DZHFFMWJXJBBRG-UHFFFAOYSA-N 0.000 description 1
NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
QYWWZCGTRUQJJF-UHFFFAOYSA-N 1-chloro-4-(4-chloro-2,5-dipropylphenyl)sulfonyl-2,5-dipropylbenzene Chemical compound C1=C(Cl)C(CCC)=CC(S(=O)(=O)C=2C(=CC(Cl)=C(CCC)C=2)CCC)=C1CCC QYWWZCGTRUQJJF-UHFFFAOYSA-N 0.000 description 1
PLVUIVUKKJTSDM-UHFFFAOYSA-N 1-fluoro-4-(4-fluorophenyl)sulfonylbenzene Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CC=C(F)C=C1 PLVUIVUKKJTSDM-UHFFFAOYSA-N 0.000 description 1
QORAVNMWUNPXAO-UHFFFAOYSA-N 2,2',4,4'-tetrachlorobiphenyl Chemical group ClC1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1Cl QORAVNMWUNPXAO-UHFFFAOYSA-N 0.000 description 1
ZWMYTAHVFFRQTD-UHFFFAOYSA-N 2,4-dibromo-3-(2,6-dibromo-3,5-dimethylphenyl)-1,5-dimethylbenzene Chemical group CC1=CC(C)=C(Br)C(C=2C(=C(C)C=C(C)C=2Br)Br)=C1Br ZWMYTAHVFFRQTD-UHFFFAOYSA-N 0.000 description 1
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical compound NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 1
MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 description 1
YTBRNEUEFCNVHC-UHFFFAOYSA-N 4,4'-dichlorobiphenyl Chemical group C1=CC(Cl)=CC=C1C1=CC=C(Cl)C=C1 YTBRNEUEFCNVHC-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
JSPGSVIGUXWPKI-UHFFFAOYSA-N 4-aminobenzenethiol Chemical compound NC1=CC=C(C=C1)S.NC1=CC=C(C=C1)S JSPGSVIGUXWPKI-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000003435 aroyl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
229910052792 caesium Inorganic materials 0.000 description 1
TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 1
HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000004918 carbon fiber reinforced polymer Substances 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
IBSGAWQJFSDRBJ-UHFFFAOYSA-M cesium sulfanide Chemical compound [SH-].[Cs+] IBSGAWQJFSDRBJ-UHFFFAOYSA-M 0.000 description 1
239000000805 composite resin Substances 0.000 description 1
238000007596 consolidation process Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
QTNDMWXOEPGHBT-UHFFFAOYSA-N dicesium;sulfide Chemical compound [S-2].[Cs+].[Cs+] QTNDMWXOEPGHBT-UHFFFAOYSA-N 0.000 description 1
229940117389 dichlorobenzene Drugs 0.000 description 1
150000004816 dichlorobenzenes Chemical class 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
239000004744 fabric Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229940060037 fluorine Drugs 0.000 description 1
235000019000 fluorine Nutrition 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
CKAPSXZOOQJIBF-UHFFFAOYSA-N hexachlorobenzene Chemical compound ClC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl CKAPSXZOOQJIBF-UHFFFAOYSA-N 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000010952 in-situ formation Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229910000103 lithium hydride Inorganic materials 0.000 description 1
GLNWILHOFOBOFD-UHFFFAOYSA-N lithium sulfide Chemical compound [Li+].[Li+].[S-2] GLNWILHOFOBOFD-UHFFFAOYSA-N 0.000 description 1
HXQGSILMFTUKHI-UHFFFAOYSA-M lithium;sulfanide Chemical compound S[Li] HXQGSILMFTUKHI-UHFFFAOYSA-M 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
150000004692 metal hydroxides Chemical class 0.000 description 1
229910044991 metal oxide Inorganic materials 0.000 description 1
150000004706 metal oxides Chemical class 0.000 description 1
238000005065 mining Methods 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920005672 polyolefin resin Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
ZOCLAPYLSUCOGI-UHFFFAOYSA-M potassium hydrosulfide Chemical compound [SH-].[K+] ZOCLAPYLSUCOGI-UHFFFAOYSA-M 0.000 description 1
DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
LXOXXUIVMOYGST-UHFFFAOYSA-M rubidium(1+);sulfanide Chemical compound [SH-].[Rb+] LXOXXUIVMOYGST-UHFFFAOYSA-M 0.000 description 1
AHKSSQDILPRNLA-UHFFFAOYSA-N rubidium(1+);sulfide Chemical compound [S-2].[Rb+].[Rb+] AHKSSQDILPRNLA-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229910052712 strontium Inorganic materials 0.000 description 1
CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
229920001897 terpolymer Polymers 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
150000003672 ureas Chemical class 0.000 description 1

Landscapes

Reinforced Plastic Materials (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA002023864A 1989-07-24 1990-08-23 Matieres composites de resine thermoplastique/fibres de carbone a grande resistance Abandoned CA2023864A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA002023864A CA2023864A1 (fr)	1989-07-24	1990-08-23	Matieres composites de resine thermoplastique/fibres de carbone a grande resistance

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/383,751 US5039572A (en)	1989-07-24	1989-07-24	High strength thermoplastic resin/carbon fiber composites and methods
CA002023864A CA2023864A1 (fr)	1989-07-24	1990-08-23	Matieres composites de resine thermoplastique/fibres de carbone a grande resistance

Publications (1)

Publication Number	Publication Date
CA2023864A1 true CA2023864A1 (fr)	1992-02-24

Family

ID=25674274

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002023864A Abandoned CA2023864A1 (fr)	1989-07-24	1990-08-23	Matieres composites de resine thermoplastique/fibres de carbone a grande resistance

Country Status (1)

Country	Link
CA (1)	CA2023864A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2393856A4 (fr) *	2009-02-05	2013-12-18	Arkema Inc	Fibres encollées avec des polyéthercétonecétones

1990
- 1990-08-23 CA CA002023864A patent/CA2023864A1/fr not_active Abandoned

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2393856A4 (fr) *	2009-02-05	2013-12-18	Arkema Inc	Fibres encollées avec des polyéthercétonecétones
US8829108B2 (en)	2009-02-05	2014-09-09	Arkema Inc.	Fibers sized with polyetherketoneketones
US9657437B2 (en)	2009-02-05	2017-05-23	Arkema Inc.	Fibers sized with polyethereketoneketones
US10030333B2 (en)	2009-02-05	2018-07-24	Arkema Inc.	Fibers sized with polyetherketoneketones
US10443189B2 (en)	2009-02-05	2019-10-15	Arkema Inc.	Fibers sized with polyetherketoneketones
US11168024B2 (en)	2009-02-05	2021-11-09	Arkema France	Fibers sized with polyetherketoneketones

Legal Events

Date	Code	Title	Description
1993-02-23	FZDE	Discontinued
2023-05-26	FZDE	Discontinued	Effective date: 19930223

Publication	Publication Date	Title
US5039572A (en)	1991-08-13	High strength thermoplastic resin/carbon fiber composites and methods
CA1324225C (fr)	1993-11-09	Composition a base de polysulfure de phenylene et procede de preparation
US4820800A (en)	1989-04-11	Arylene sulfide polymers
US5780583A (en)	1998-07-14	Reactive polyarylene sulfide oligomers
US5093155A (en)	1992-03-03	Process for sizing reinforcing fiber by applying sulfone compounds containing sulfonyl groups and sized reinforcing fibers obtained thereby
JP4608715B2 (ja)	2011-01-12	ポリアリーレンスルフィドの製造方法
US3763124A (en)	1973-10-02	Treatment of the alkali metal sulfide reactant to reduce impurities and its reaction with a polyhalo substituted aromatic compound
KR100262252B1 (ko)	2000-08-01	폴리(아릴렌술파이드)중합체의 제조 방법
US4812552A (en)	1989-03-14	Process for preparing poly(arylene sulfide ketone) with water addition
US5017643A (en)	1991-05-21	Composition and process for making poly (arylene sulfide) resins reinforced with glass fibers
US5298318A (en)	1994-03-29	Poly(arylene sulfide) resins reinforced with glass fibers
CA1306575C (fr)	1992-08-18	Production de polymeres aromatiques sulfure/cetone
JP3598510B2 (ja)	2004-12-08	繊維強化複合材料
EP0374719B1 (fr)	1996-01-31	Sulfure de polyarylène de haut poids moléculaire et procédé pour le préparer
US5134224A (en)	1992-07-28	Aromatic sulfide/sulfone polymer production
US5015702A (en)	1991-05-14	Treatment of poly(arylene sulfide/sulfone) polymers
CA1312410C (fr)	1993-01-05	Mode de production de production de polymeres lineaires, branches ou modifies
CA2009241A1 (fr)	1990-08-27	Production de polymeres aromatiques sulfure/cetone
CA1309551C (fr)	1992-10-27	Preparation du poly (sulfure d'arylene)
JPH04173840A (ja)	1992-06-22	高強度熱可塑性樹脂複合材料
US4762911A (en)	1988-08-09	Process for the preparation of high-molecular, optionally branched polyarylene sulphide with sodium sulfide, potassium sulfide and hydrogen sulfide
JPS58183750A (ja)	1983-10-27	導電性を有する熱可塑性樹脂組成物
US5045367A (en)	1991-09-03	Reinforced plastic comprising fibrous reinforcement treated with poly(arylene sulfide sulfone) polymer containing ether groups
US5110901A (en)	1992-05-05	Higher molecular weight arylene sulfide resin and process for its preparation
US4958004A (en)	1990-09-18	Aromatic sulfide/sulfone polymer production