JP6051987B2

JP6051987B2 - サイジング剤塗布炭素繊維の製造方法

サイジング剤塗布炭素繊維の製造方法 Download PDF

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Publication number: JP6051987B2
Authority: JP; Japan
Prior art keywords: sizing agent; carbon fiber; epoxy; epoxy compound; value
Prior art date: 2013-03-19
Legal status : Active

Application number

JP2013056148A

Other languages

English (en)

Japanese (ja)

Other versions

JP2014181418A5 (cg-RX-API-DMAC7.html

JP2014181418A (ja

Inventor

市川　智子

智子市川

大悟小林

遠藤　真

真遠藤

Current Assignee

Toray Industries Inc

Original Assignee

Toray Industries Inc

Priority date

2013-03-19

Filing date

2013-03-19

Publication date

2016-12-27

2013-03-19 Application filed by Toray Industries Inc filed Critical Toray Industries Inc

2013-03-19 Priority to JP2013056148A priority Critical patent/JP6051987B2/ja

2014-09-29 Publication of JP2014181418A publication Critical patent/JP2014181418A/ja

2016-01-28 Publication of JP2014181418A5 publication Critical patent/JP2014181418A5/ja

2016-12-27 Application granted granted Critical

2016-12-27 Publication of JP6051987B2 publication Critical patent/JP6051987B2/ja

Status Active legal-status Critical Current

2033-03-19 Anticipated expiration legal-status Critical

Links

239000003795 chemical substances by application Substances 0.000 title claims description 299
229920000049 Carbon (fiber) Polymers 0.000 title claims description 286
239000004917 carbon fiber Substances 0.000 title claims description 286
238000004513 sizing Methods 0.000 title claims description 265
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims description 251
238000004519 manufacturing process Methods 0.000 title claims description 22
239000004593 Epoxy Substances 0.000 claims description 219
150000001875 compounds Chemical class 0.000 claims description 173
238000000034 method Methods 0.000 claims description 82
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
238000010438 heat treatment Methods 0.000 claims description 54
125000003700 epoxy group Chemical group 0.000 claims description 49
239000007788 liquid Substances 0.000 claims description 31
239000002904 solvent Substances 0.000 claims description 31
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 27
125000001931 aliphatic group Chemical group 0.000 claims description 23
239000011248 coating agent Substances 0.000 claims description 22
238000000576 coating method Methods 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 21
150000002367 halogens Chemical class 0.000 claims description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
238000004833 X-ray photoelectron spectroscopy Methods 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 16
238000001035 drying Methods 0.000 claims description 14
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
229910052757 nitrogen Inorganic materials 0.000 claims description 11
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 7
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
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FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 4
HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 claims description 4
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 4
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WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
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239000011347 resin Substances 0.000 description 77
238000001723 curing Methods 0.000 description 51
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125000000524 functional group Chemical group 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 31
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229920005992 thermoplastic resin Polymers 0.000 description 28
239000000835 fiber Substances 0.000 description 27
239000002245 particle Substances 0.000 description 25
239000011208 reinforced composite material Substances 0.000 description 24
229920001187 thermosetting polymer Polymers 0.000 description 24
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 19
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239000000126 substance Substances 0.000 description 18
238000005259 measurement Methods 0.000 description 17
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239000002585 base Substances 0.000 description 16
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239000007864 aqueous solution Substances 0.000 description 15
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230000003647 oxidation Effects 0.000 description 15
238000007254 oxidation reaction Methods 0.000 description 15
229910052760 oxygen Inorganic materials 0.000 description 15
125000003118 aryl group Chemical group 0.000 description 14
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
239000001301 oxygen Substances 0.000 description 14
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239000000460 chlorine Substances 0.000 description 12
239000000463 material Substances 0.000 description 12
239000000523 sample Substances 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 11
239000002131 composite material Substances 0.000 description 11
229920001971 elastomer Polymers 0.000 description 11
239000008151 electrolyte solution Substances 0.000 description 11
238000009987 spinning Methods 0.000 description 11
230000000694 effects Effects 0.000 description 10
239000000243 solution Substances 0.000 description 10
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239000005060 rubber Substances 0.000 description 9
238000003860 storage Methods 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000004952 Polyamide Substances 0.000 description 8
239000007791 liquid phase Substances 0.000 description 8
AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 8
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
150000004982 aromatic amines Chemical class 0.000 description 7
239000004202 carbamide Substances 0.000 description 7
239000001257 hydrogen Substances 0.000 description 7
229910052739 hydrogen Inorganic materials 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
229930185605 Bisphenol Natural products 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000007385 chemical modification Methods 0.000 description 6
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QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 6
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239000007789 gas Substances 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
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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 5
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 5
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KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 5
229910000831 Steel Inorganic materials 0.000 description 5
239000001099 ammonium carbonate Substances 0.000 description 5
PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 5
230000008859 change Effects 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
230000006866 deterioration Effects 0.000 description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
230000003993 interaction Effects 0.000 description 5
238000002156 mixing Methods 0.000 description 5
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 5
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239000010959 steel Substances 0.000 description 5
238000009864 tensile test Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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239000004695 Polyether sulfone Substances 0.000 description 4
239000004642 Polyimide Substances 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229920004738 ULTEM® Polymers 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
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230000000052 comparative effect Effects 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
150000002366 halogen compounds Chemical class 0.000 description 4
238000005470 impregnation Methods 0.000 description 4
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239000002243 precursor Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
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238000003763 carbonization Methods 0.000 description 3
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238000007865 diluting Methods 0.000 description 3
238000007598 dipping method Methods 0.000 description 3
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229910052731 fluorine Inorganic materials 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
238000005227 gel permeation chromatography Methods 0.000 description 3
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 3
239000012943 hotmelt Substances 0.000 description 3
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229910052751 metal Inorganic materials 0.000 description 3
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238000002166 wet spinning Methods 0.000 description 3
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229920000297 Rayon Polymers 0.000 description 2
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