JPH01314785A - 複合材用繊維の処理剤及びその製造方法 - Google Patents
複合材用繊維の処理剤及びその製造方法Info
- Publication number
- JPH01314785A JPH01314785A JP63147532A JP14753288A JPH01314785A JP H01314785 A JPH01314785 A JP H01314785A JP 63147532 A JP63147532 A JP 63147532A JP 14753288 A JP14753288 A JP 14753288A JP H01314785 A JPH01314785 A JP H01314785A
- Authority
- JP
- Japan
- Prior art keywords
- fibers
- hydroxyl group
- polyoxyethylene
- fiber
- treatment agent
- 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.)
- Granted
Links
- 239000000835 fiber Substances 0.000 title claims abstract description 114
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 112
- 239000002131 composite material Substances 0.000 title claims abstract description 32
- 238000004519 manufacturing process Methods 0.000 title claims description 17
- -1 polyoxyethylene Polymers 0.000 claims abstract description 80
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 63
- 239000003822 epoxy resin Substances 0.000 claims abstract description 34
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 34
- 229920003171 Poly (ethylene oxide) Polymers 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 14
- 239000012948 isocyanate Substances 0.000 claims description 9
- 150000002513 isocyanates Chemical class 0.000 claims description 9
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 4
- 229920000049 Carbon (fiber) Polymers 0.000 abstract description 43
- 239000004917 carbon fiber Substances 0.000 abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 38
- 229920006231 aramid fiber Polymers 0.000 abstract description 31
- 239000007788 liquid Substances 0.000 abstract description 26
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 18
- 239000007787 solid Substances 0.000 abstract description 15
- 239000000463 material Substances 0.000 abstract description 7
- 125000001931 aliphatic group Chemical group 0.000 abstract description 3
- 238000004513 sizing Methods 0.000 abstract description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- 239000003733 fiber-reinforced composite Substances 0.000 abstract 1
- 239000012783 reinforcing fiber Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 25
- 239000004760 aramid Substances 0.000 description 21
- 239000007864 aqueous solution Substances 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 18
- 239000002202 Polyethylene glycol Substances 0.000 description 13
- 229920001223 polyethylene glycol Polymers 0.000 description 13
- 238000001556 precipitation Methods 0.000 description 13
- 239000000839 emulsion Substances 0.000 description 12
- 230000008719 thickening Effects 0.000 description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 238000000862 absorption spectrum Methods 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 125000005442 diisocyanate group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 238000005452 bending Methods 0.000 description 4
- 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 4
- 238000011049 filling Methods 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000002990 reinforced plastic Substances 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002430 Fibre-reinforced plastic Polymers 0.000 description 3
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 3
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000011151 fibre-reinforced plastic Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000004846 water-soluble epoxy resin Substances 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229920003319 Araldite® Polymers 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 2
- 239000011261 inert gas Substances 0.000 description 2
- 125000006353 oxyethylene group Chemical group 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- DEMHZMDSLWQANG-UHFFFAOYSA-N N=C=O.N=C=O.C1CCC1 Chemical compound N=C=O.N=C=O.C1CCC1 DEMHZMDSLWQANG-UHFFFAOYSA-N 0.000 description 1
- PEYZIFREGNMXEE-UHFFFAOYSA-N N=C=O.N=C=O.C1CCCCC1C(C)(C)C1CCCCC1 Chemical compound N=C=O.N=C=O.C1CCCCC1C(C)(C)C1CCCCC1 PEYZIFREGNMXEE-UHFFFAOYSA-N 0.000 description 1
- WMTLVUCMBWBYSO-UHFFFAOYSA-N N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 Chemical compound N=C=O.N=C=O.C=1C=CC=CC=1OC1=CC=CC=C1 WMTLVUCMBWBYSO-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- OKTJSMMVPCPJKN-BJUDXGSMSA-N carbon-11 Chemical compound [11C] OKTJSMMVPCPJKN-BJUDXGSMSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 238000009990 desizing Methods 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000005313 fatty acid group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001246 polyethylene glycol monostearate Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
Landscapes
- Reinforced Plastic Materials (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Alloys Or Alloy Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63147532A JPH01314785A (ja) | 1988-06-15 | 1988-06-15 | 複合材用繊維の処理剤及びその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP63147532A JPH01314785A (ja) | 1988-06-15 | 1988-06-15 | 複合材用繊維の処理剤及びその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01314785A true JPH01314785A (ja) | 1989-12-19 |
| JPH0325550B2 JPH0325550B2 (enExample) | 1991-04-08 |
Family
ID=15432441
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63147532A Granted JPH01314785A (ja) | 1988-06-15 | 1988-06-15 | 複合材用繊維の処理剤及びその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH01314785A (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011252132A (ja) * | 2010-06-04 | 2011-12-15 | Shinto Paint Co Ltd | 自己乳化性のエポキシ樹脂組成物 |
| JP2016196711A (ja) * | 2015-04-03 | 2016-11-24 | Dic株式会社 | 繊維集束剤ならびに集束されたガラス繊維及び炭素繊維 |
| WO2018079763A1 (ja) | 2016-10-28 | 2018-05-03 | 三菱ケミカル株式会社 | 炭素繊維用サイジング剤、炭素繊維用サイジング剤の水分散液、及びサイジング剤付着炭素繊維束 |
| CN108547372A (zh) * | 2018-04-12 | 2018-09-18 | 中建局集团第三建筑有限公司 | 一种临时移动厕所化粪池及其施工方法 |
| JP2024019220A (ja) * | 2022-03-31 | 2024-02-08 | 明成化学工業株式会社 | 架橋剤組成物、ゴム補強用繊維処理剤、ゴム補強用繊維処理剤キット及びゴム補強用繊維の製造方法 |
-
1988
- 1988-06-15 JP JP63147532A patent/JPH01314785A/ja active Granted
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011252132A (ja) * | 2010-06-04 | 2011-12-15 | Shinto Paint Co Ltd | 自己乳化性のエポキシ樹脂組成物 |
| JP2016196711A (ja) * | 2015-04-03 | 2016-11-24 | Dic株式会社 | 繊維集束剤ならびに集束されたガラス繊維及び炭素繊維 |
| WO2018079763A1 (ja) | 2016-10-28 | 2018-05-03 | 三菱ケミカル株式会社 | 炭素繊維用サイジング剤、炭素繊維用サイジング剤の水分散液、及びサイジング剤付着炭素繊維束 |
| KR20190045355A (ko) | 2016-10-28 | 2019-05-02 | 미쯔비시 케미컬 주식회사 | 탄소섬유용 사이징제, 탄소섬유용 사이징제의 수분산액, 및 사이징제 부착 탄소섬유속 |
| KR20210062745A (ko) | 2016-10-28 | 2021-05-31 | 미쯔비시 케미컬 주식회사 | 탄소섬유용 사이징제, 탄소섬유용 사이징제의 수분산액, 및 사이징제 부착 탄소섬유속 |
| US11787913B2 (en) | 2016-10-28 | 2023-10-17 | Mitsubishi Chemical Corporation | Sizing agent for carbon fibers, aqueous dispersion of sizing agent for carbon fibers, and sizing agent-adhered carbon fiber bundle |
| CN108547372A (zh) * | 2018-04-12 | 2018-09-18 | 中建局集团第三建筑有限公司 | 一种临时移动厕所化粪池及其施工方法 |
| JP2024019220A (ja) * | 2022-03-31 | 2024-02-08 | 明成化学工業株式会社 | 架橋剤組成物、ゴム補強用繊維処理剤、ゴム補強用繊維処理剤キット及びゴム補強用繊維の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0325550B2 (enExample) | 1991-04-08 |
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