JPH0242940B2 - - Google Patents
Info
- Publication number
- JPH0242940B2 JPH0242940B2 JP57190353A JP19035382A JPH0242940B2 JP H0242940 B2 JPH0242940 B2 JP H0242940B2 JP 57190353 A JP57190353 A JP 57190353A JP 19035382 A JP19035382 A JP 19035382A JP H0242940 B2 JPH0242940 B2 JP H0242940B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon fibers
- fibers
- amines
- present
- treatment
- 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.)
- Expired - Lifetime
Links
- 229920000049 Carbon (fiber) Polymers 0.000 claims description 13
- 239000004917 carbon fiber Substances 0.000 claims description 13
- 239000000835 fiber Substances 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 9
- -1 amine compound Chemical class 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910002804 graphite Inorganic materials 0.000 claims description 6
- 239000010439 graphite Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 238000004381 surface treatment Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- 229910020366 ClO 4 Inorganic materials 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BMFVGAAISNGQNM-UHFFFAOYSA-N isopentylamine Chemical compound CC(C)CCN BMFVGAAISNGQNM-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- CJVYYDCBKKKIPD-UHFFFAOYSA-N 1-n,1-n,2-n,2-n-tetramethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N(C)C CJVYYDCBKKKIPD-UHFFFAOYSA-N 0.000 description 1
- UMAPFAAAQBMYNJ-UHFFFAOYSA-N 1-n,2-n-dimethylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1NC UMAPFAAAQBMYNJ-UHFFFAOYSA-N 0.000 description 1
- BBRHQNMMUUMVDE-UHFFFAOYSA-N 1-n,2-n-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1NC(C)CNC1=CC=CC=C1 BBRHQNMMUUMVDE-UHFFFAOYSA-N 0.000 description 1
- ZPGZNKGKCSYBGK-UHFFFAOYSA-N 1-n-[4-(dimethylamino)phenyl]-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC=C(N(C)C)C=C1 ZPGZNKGKCSYBGK-UHFFFAOYSA-N 0.000 description 1
- DCBKKCYNUSINPI-UHFFFAOYSA-N 2,3,4,5,6-pentamethylaniline Chemical compound CC1=C(C)C(C)=C(N)C(C)=C1C DCBKKCYNUSINPI-UHFFFAOYSA-N 0.000 description 1
- CDULGHZNHURECF-UHFFFAOYSA-N 2,3-dimethylaniline 2,4-dimethylaniline 2,5-dimethylaniline 2,6-dimethylaniline 3,4-dimethylaniline 3,5-dimethylaniline Chemical group CC1=CC=C(N)C(C)=C1.CC1=CC=C(C)C(N)=C1.CC1=CC(C)=CC(N)=C1.CC1=CC=C(N)C=C1C.CC1=CC=CC(N)=C1C.CC1=CC=CC(C)=C1N CDULGHZNHURECF-UHFFFAOYSA-N 0.000 description 1
- BMIPMKQAAJKBKP-UHFFFAOYSA-N 2,4,5-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C=C1C BMIPMKQAAJKBKP-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-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
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- HJXIRCMNJLIHQR-UHFFFAOYSA-N 2-n,2-n-dimethylbenzene-1,2-diamine Chemical compound CN(C)C1=CC=CC=C1N HJXIRCMNJLIHQR-UHFFFAOYSA-N 0.000 description 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
- DNIDAYOSPDNUKP-UHFFFAOYSA-N 3-(2-phenylethenyl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C=CC=2C=CC=CC=2)=C1N DNIDAYOSPDNUKP-UHFFFAOYSA-N 0.000 description 1
- YGOFNNAZFZYNIX-UHFFFAOYSA-N 3-N-phenylbenzene-1,2,3-triamine Chemical compound NC=1C(=C(C=CC1)NC1=CC=CC=C1)N YGOFNNAZFZYNIX-UHFFFAOYSA-N 0.000 description 1
- RQUPXQYTWVIBIV-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)aniline Chemical compound CCC(C)(C)C1=CC=C(N)C=C1 RQUPXQYTWVIBIV-UHFFFAOYSA-N 0.000 description 1
- RHPVVNRNAHRJOQ-UHFFFAOYSA-N 4-methyl-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1NC1=CC=C(C)C=C1 RHPVVNRNAHRJOQ-UHFFFAOYSA-N 0.000 description 1
- WRDWWAVNELMWAM-UHFFFAOYSA-N 4-tert-butylaniline Chemical compound CC(C)(C)C1=CC=C(N)C=C1 WRDWWAVNELMWAM-UHFFFAOYSA-N 0.000 description 1
- IBDUWDDUJSWRTJ-UHFFFAOYSA-N 5-methyl-2-propan-2-ylaniline Chemical compound CC(C)C1=CC=C(C)C=C1N IBDUWDDUJSWRTJ-UHFFFAOYSA-N 0.000 description 1
- UPMCDOMOBNMTPH-UHFFFAOYSA-N 6-phenyl-5,6-dihydroimidazo[2,1-b][1,3]thiazole Chemical compound N1=C2SC=CN2CC1C1=CC=CC=C1 UPMCDOMOBNMTPH-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 229910013684 LiClO 4 Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- NIPLIJLVGZCKMP-UHFFFAOYSA-M Neurine Chemical compound [OH-].C[N+](C)(C)C=C NIPLIJLVGZCKMP-UHFFFAOYSA-M 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 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 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- NOUUUQMKVOUUNR-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCNC1=CC=CC=C1 NOUUUQMKVOUUNR-UHFFFAOYSA-N 0.000 description 1
- JDEJGVSZUIJWBM-UHFFFAOYSA-N n,n,2-trimethylaniline Chemical compound CN(C)C1=CC=CC=C1C JDEJGVSZUIJWBM-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- ZUHZZVMEUAUWHY-UHFFFAOYSA-N n,n-dimethylpropan-1-amine Chemical compound CCCN(C)C ZUHZZVMEUAUWHY-UHFFFAOYSA-N 0.000 description 1
- LXZGVFCKZRHKMU-UHFFFAOYSA-N n-benzyl-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CC1=CC=CC=C1 LXZGVFCKZRHKMU-UHFFFAOYSA-N 0.000 description 1
- PZUGJLOCXUNFLM-UHFFFAOYSA-N n-ethenylaniline Chemical compound C=CNC1=CC=CC=C1 PZUGJLOCXUNFLM-UHFFFAOYSA-N 0.000 description 1
- FNLUJDLKYOWMMF-UHFFFAOYSA-N n-ethyl-2-methylpropan-1-amine Chemical compound CCNCC(C)C FNLUJDLKYOWMMF-UHFFFAOYSA-N 0.000 description 1
- WOLFCKKMHUVEPN-UHFFFAOYSA-N n-ethyl-n-methylbutan-1-amine Chemical compound CCCCN(C)CC WOLFCKKMHUVEPN-UHFFFAOYSA-N 0.000 description 1
- ITMSSZATZARZCA-UHFFFAOYSA-N n-ethyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CC)C1=CC=CC=C1 ITMSSZATZARZCA-UHFFFAOYSA-N 0.000 description 1
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical class [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical compound CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003115 supporting electrolyte Substances 0.000 description 1
- 238000005211 surface analysis Methods 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
Landscapes
- Chemical Or Physical Treatment Of Fibers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
【発明の詳細な説明】
本発明は、黒鉛繊維を含む炭素繊維の表面処理
法に関するものである。
複合体材料の強度特性および耐久性は特に悪条
件の環境において、試材料の二面間の結合強度、
即ち炭素繊維と複合樹脂マトリツクスとの間の結
合強度に非常に左右される。
そこで炭素繊維を樹脂等に、充填する際に両者
の接着性を良好ならしめるため表面処理を施すこ
とが必要である。
かかる処理方法として、種々の手法、装置等が
提案されているが、従来の方法のほとんどが炭素
繊維の表面に、酸化物を形成せしめる方法であ
る。すなわち、炭素繊維もしくは黒鉛繊維に液相
ないし気相による酸化処理を施すことによつて繊
維の表面に−COOH、−OH、−Ｃ＝Ｏ基を形成、
又は繊維の表面積を増大せしめることにより、樹
脂マトリツクスとの親和性、接着性を改善する方
法である。
しかしながら、繊維を酸化する方法は、樹脂と
の充分に強い接着力が得られないこと、酸化処理
条件を強めると繊維の強度を劣化させる等の欠点
を有している。
そこで、本発明者らは、かかるる現状に鑑み、
鋭意検討した結果、本発明に致達したものであ
る。すなわち本発明は、炭素繊維表面に、−NH
基等の官能基を形成せしめる、又は−NH基等の
官能基を持つた化合物を吸着せしめることによつ
て、樹脂との親和性、接着性を改善させることを
目的として、塩基性有機アミン存在下で水溶液中
で通電処理する方法である。
本発明に用いられる塩基性有機アミンとは、脂
肪族アミンの第１級アミンとして、メチルアミ
ン、エチルアミン、プロピルアミン、イソプロピ
ルアミン、ブチルアミン、イソブチルアミン、
sec−ブチルアミン、tert−ブチルアミン、ペン
チルアミン、イソペンチルアミン、tert−ペンチ
ルアミン、ヘキシルアミン、ヘプチルアミン、オ
クチルアミン、２−エチルヘキシルアミン、ノニ
ルアミン、デシルアミン、ビニルアミン、アリル
アミン等、脂肪族の第２級アミンとして、ジメチ
ルアミン、ジエチルアミン、ジプロピルアミン、
ジイソプロピルアミン、Ｎ−メチルエチルアミ
ン、Ｎ−エチルイソブチルアミン等、第３級アミ
ンとして、トリメチルアミン、トリエチルアミ
ン、Ｎ，Ｎ−ジメチルプロピルアミン、Ｎ−エチ
ル−Ｎ−メチルブチルアミン、第４級アンモニウ
ム化合物としてテトラメチルアンモニウムの塩化
物もしくは臭化物、テトラエチルアンモニウムの
塩化物もしくは臭化物、ノイリン、ジアミン及び
ポリアミン類としてエチレンジアミン、プロピレ
ンジアミン、トリメチレンジアミン、テトラメチ
レンジアミン、ペンタメチレンジアミン、ヘキサ
メチレンジアミン、ビス（２−アミノエチル）ア
ミン、３，６，９−トリアザ−１，11−ウンデカ
ンジアミン、その他の脂肪族アミンとしてジシア
ンジアミド及びアミノアルコール類、芳香族アミ
ンのモノアミンとしてアニリン、トルイジン、エ
チルアニリン、ｐ−イソプロピルアニリン、ｐ−
tert−ブチルアニリン、ｐ−tert−ペンチルアニ
リン、キシリジン、２−イソプロピル−５−メチ
ルアニリン、２，４，５−トリメチルアニリン、
２，４，６−トリメチルアニリン、ペンタメチル
アニリン、ビニルアニリン、Ｎ−メチルアニリ
ン、Ｎ−エチルアニリン、Ｎ−メチルトルイジ
ン、Ｎ，Ｎ−ジメチルアニリン、Ｎ，Ｎ−ジエチ
ルアニリン、Ｎ，Ｎ−ジメチルトルイジン、ジフ
エニルアミン、ジ−ｐ−トリルアミン、Ｎ−メチ
ルジフエニルアミン、Ｎ−エチルジフエニルアミ
ン、トリフエニルアミン、Ｎ−ベンジル−Ｎ−メ
チルアニリン、Ｎ，Ｎ−ジベンジルアニリン、芳
香族のジアミン及びポリアミンとして、フエニレ
ンジアミン、トルエンジアミン、Ｎ−メチルフエ
ニレンジアミン、Ｎ，Ｎ−ジメチルフエニレンジ
アミン、Ｎ，N′−ジメチルフエニレンジアミン、
Ｎ，Ｎ，N′，N′−テトラメチルフエニレンジア
ミン、アミノジフエニルアミン、ジアミノジフエ
ニルアミン、４，4′−ビス（ジメチルアミノ）ジ
フエニルアミン、ベンゼントリアミン、Ｎ，
N′−ジフエニルエチレンジアミン、Ｎ，N′−ジ
フエニルプロピレンジアミン、スチルベンジアミ
ン、アンモニウム塩としてトリメチルフエニルア
ンモニウム−ヨージド、ベンジルジメチルフエニ
ルアンモニウムクロリド、その他芳香族アミンと
して、ハロゲンのアニリン類、ニトロソ及びニト
ロアニリン類、アルコキシアニリン類、アラルキ
ルアミン、ピリジン類等のことを総称する。
本発明において、水溶液中で通電処理するに当
り、支持電解質として、過酸素酸塩たとえば
LiClO4、NH4ClO4、Et4ClO4等を用いてもよい。
本発明の方法で、溶媒に水を使用すると、繊維
と樹脂との密着性が良くなる。溶媒に水を使用す
ることの利点は、取り扱い性、安全性を高めるの
で工業的には有利な方法である。炭素繊維もしく
は、黒鉛繊維とアミンが如何なる反応を起してい
るかは明確でないが、ESCAによつて、炭素繊維
もしくは黒鉛繊維中の窒素量の増加が認められ、
化学反応によつてアミンが付着していることは明
らかであり、吸着によるアミンの付着や陰極還元
による表面の改質等も考えられる。
本発明の水溶液中で炭素繊維もしくは黒鉛繊維
を陽極又は陰極として通電処理を行うに当り、ア
ミン濃度、電圧、電流密度、通電時の温度、時間
等はそれぞれの系で適宜選択されるが、特に電流
密度をあげ効果を向上させるには、通常１〜10ボ
ルト、電流密度は0.01〜１アンペア／ｄm2、好ま
しくは２〜５ボルト、電流密度は0.05〜0.2アン
ペア／ｄm2を適用する。温度は室温〜60℃までが
反応を行うに当り便利である。又支持電解質の濃
度も特に制限を受けない。
以上によつて得られた炭素繊維を複合材料とし
て使用するに当り、相手のマトリツクスについて
も特に制限がないが、通常エポキシ樹脂、不飽和
ポリエステル樹脂、ポリアセタール樹脂、ポリア
ミド樹脂等が用いられる。
以下実施例によつて本発明を説明する。
実施例 １
炭素繊維を陰極として、種々のアミン５％の水
溶液中で電流密度0.1アンペア／ｄm2になるよう
に通電処理して得られた、炭素繊維のESCAによ
る表面分析結果とマトリツクス樹脂として油化シ
エル製DX#210 100部、BF3・MEA3部を使用し
たコンポジツトのILSSを表１に示す。
【表】DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for surface treatment of carbon fibers including graphite fibers. The strength properties and durability of composite materials are determined by the strength of the bond between two surfaces of the specimen, especially in adverse environments.
That is, it is highly dependent on the bond strength between the carbon fibers and the composite resin matrix. Therefore, when filling carbon fibers into a resin or the like, it is necessary to perform surface treatment to improve the adhesion between the two. Various techniques, devices, etc. have been proposed as such treatment methods, but most of the conventional methods involve forming oxides on the surface of carbon fibers. That is, by subjecting carbon fibers or graphite fibers to oxidation treatment in a liquid phase or gas phase, -COOH, -OH, -C=O groups are formed on the surface of the fibers.
Another method is to improve the affinity and adhesion with the resin matrix by increasing the surface area of the fibers. However, the method of oxidizing fibers has drawbacks such as not being able to obtain a sufficiently strong adhesive force with the resin, and increasing the oxidation treatment conditions to deteriorate the strength of the fibers. Therefore, in view of the current situation, the present inventors
As a result of intensive study, the present invention was arrived at. That is, in the present invention, -NH
The presence of basic organic amines is intended to improve affinity and adhesion with resins by forming functional groups such as -NH groups or by adsorbing compounds with functional groups such as -NH groups. The method described below involves applying electricity in an aqueous solution. The basic organic amines used in the present invention include methylamine, ethylamine, propylamine, isopropylamine, butylamine, isobutylamine,
Aliphatic secondary amines such as sec-butylamine, tert-butylamine, pentylamine, isopentylamine, tert-pentylamine, hexylamine, heptylamine, octylamine, 2-ethylhexylamine, nonylamine, decylamine, vinylamine, allylamine, etc. as dimethylamine, diethylamine, dipropylamine,
Diisopropylamine, N-methylethylamine, N-ethylisobutylamine, etc. as tertiary amines, trimethylamine, triethylamine, N,N-dimethylpropylamine, N-ethyl-N-methylbutylamine, tetramethyl as quaternary ammonium compounds Ammonium chloride or bromide, tetraethylammonium chloride or bromide, neurin, diamines and polyamines such as ethylenediamine, propylenediamine, trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, bis(2-aminoethyl) Amine, 3,6,9-triaza-1,11-undecanediamine, other aliphatic amines such as dicyandiamide and amino alcohols, monoamines of aromatic amines such as aniline, toluidine, ethylaniline, p-isopropylaniline, p-
tert-butylaniline, p-tert-pentylaniline, xylidine, 2-isopropyl-5-methylaniline, 2,4,5-trimethylaniline,
2,4,6-trimethylaniline, pentamethylaniline, vinylaniline, N-methylaniline, N-ethylaniline, N-methyltoluidine, N,N-dimethylaniline, N,N-diethylaniline, N,N-dimethyl Toluidine, diphenylamine, di-p-tolylamine, N-methyldiphenylamine, N-ethyldiphenylamine, triphenylamine, N-benzyl-N-methylaniline, N,N-dibenzylaniline, aromatic diamines and As polyamines, phenylenediamine, toluenediamine, N-methylphenylenediamine, N,N-dimethylphenylenediamine, N,N'-dimethylphenylenediamine,
N,N,N',N'-tetramethylphenylenediamine, aminodiphenylamine, diaminodiphenylamine, 4,4'-bis(dimethylamino)diphenylamine, benzenetriamine, N,
N'-diphenylethylenediamine, N,N'-diphenylpropylenediamine, stilbenediamine, ammonium salts such as trimethylphenylammonium iodide, benzyldimethylphenylammonium chloride, and other aromatic amines such as halogen anilines, nitroso, and A general term for nitroanilines, alkoxyanilines, aralkylamines, pyridines, etc. In the present invention, when carrying out current treatment in an aqueous solution, peroxygen salts such as
LiClO 4 , NH 4 ClO 4 , Et 4 ClO 4 , etc. may also be used. When water is used as a solvent in the method of the present invention, the adhesion between the fiber and the resin is improved. The advantage of using water as a solvent is that it improves ease of handling and safety, making it an industrially advantageous method. Although it is not clear what kind of reaction occurs between carbon fibers or graphite fibers and amines, an increase in the amount of nitrogen in carbon fibers or graphite fibers was observed by ESCA.
It is clear that the amine is attached due to a chemical reaction, and it is also possible that the amine is attached due to adsorption or surface modification due to cathodic reduction. When carrying out current treatment using carbon fibers or graphite fibers as anodes or cathodes in the aqueous solution of the present invention, the amine concentration, voltage, current density, temperature and time during current application are selected as appropriate for each system, but in particular To increase the current density and improve the effect, a current density of usually 1 to 10 volts, a current density of 0.01 to 1 ampere/dm 2 , preferably 2 to 5 volts, and a current density of 0.05 to 0.2 ampere/dm 2 is applied. Temperatures ranging from room temperature to 60°C are convenient for carrying out the reaction. Furthermore, the concentration of the supporting electrolyte is not particularly limited. When using the carbon fibers obtained as described above as a composite material, there are no particular restrictions on the matrices to be used, but epoxy resins, unsaturated polyester resins, polyacetal resins, polyamide resins, etc. are usually used. The present invention will be explained below with reference to Examples. Example 1 Surface analysis results by ESCA of carbon fibers obtained by applying current to a 5% aqueous solution of various amines at a current density of 0.1 ampere/dm 2 using carbon fibers as a cathode, and oil as a matrix resin. Table 1 shows the ILSS of a composite using 100 parts of DX#210 manufactured by Kasiel and 3 parts of BF and 3 parts of MEA. 【table】
Claims (1)
合物の存在下で通電処理することを特徴とする炭
素繊維もしくは黒鉛繊維の表面処理方法。1. A method for surface treatment of carbon fibers or graphite fibers, which comprises subjecting the carbon fibers to an electrical current treatment in an aqueous solution in the presence of a basic organic amine compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19035382A JPS5982467A (en) | 1982-10-29 | 1982-10-29 | Surface modification of carbon fiber |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19035382A JPS5982467A (en) | 1982-10-29 | 1982-10-29 | Surface modification of carbon fiber |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5982467A JPS5982467A (en) | 1984-05-12 |
| JPH0242940B2 true JPH0242940B2 (en) | 1990-09-26 |
Family
ID=16256775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19035382A Granted JPS5982467A (en) | 1982-10-29 | 1982-10-29 | Surface modification of carbon fiber |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5982467A (en) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2564489B1 (en) * | 1984-05-18 | 1986-10-10 | Onera (Off Nat Aerospatiale) | ELECTROCHEMICAL PROCESS FOR THE SURFACE TREATMENT OF CARBON FIBERS, FIBER TREATED BY THIS PROCESS AND COMPOSITE MATERIAL COMPRISING SUCH FIBERS |
| FR2672307B1 (en) * | 1991-02-01 | 1993-06-04 | Centre Nat Rech Scient | METHOD FOR MODIFYING THE SURFACE OF CARBON MATERIALS BY ELECTROCHEMICAL REDUCTION OF DIAZONIUM SALTS, PARTICULARLY CARBON FIBERS FOR COMPOSITE MATERIALS, CARBON MATERIALS THUS MODIFIED. |
| US5869550A (en) * | 1995-05-22 | 1999-02-09 | Cabot Corporation | Method to improve traction using silicon-treated carbon blacks |
| US6069190A (en) * | 1996-06-14 | 2000-05-30 | Cabot Corporation | Ink compositions having improved latency |
| US5922118A (en) * | 1996-06-14 | 1999-07-13 | Cabot Corporation | Modified colored pigments and ink jet inks, inks, and coatings containing modified colored pigments |
| US5707432A (en) * | 1996-06-14 | 1998-01-13 | Cabot Corporation | Modified carbon products and inks and coatings containing modified carbon products |
| US6110994A (en) * | 1996-06-14 | 2000-08-29 | Cabot Corporation | Polymeric products containing modified carbon products and methods of making and using the same |
| WO1998013418A1 (en) * | 1996-09-25 | 1998-04-02 | Cabot Corporation | Pre-coupled silicon-treated carbon blacks |
| US6017980A (en) * | 1997-03-27 | 2000-01-25 | Cabot Corporation | Elastomeric compounds incorporating metal-treated carbon blacks |
| US5904762A (en) * | 1997-04-18 | 1999-05-18 | Cabot Corporation | Method of making a multi-phase aggregate using a multi-stage process |
| US5895522A (en) * | 1997-08-12 | 1999-04-20 | Cabot Corporation | Modified carbon products with leaving groups and inks and coatings containing modified carbon products |
| US6368239B1 (en) | 1998-06-03 | 2002-04-09 | Cabot Corporation | Methods of making a particle having an attached stable free radical |
| EP1178085A3 (en) | 1997-10-31 | 2004-05-12 | Cabot Corporation | Particles having an attached stable free radical, polymerized modified particles, and methods of making the same |
| US6068688A (en) * | 1997-11-12 | 2000-05-30 | Cabot Corporation | Particle having an attached stable free radical and methods of making the same |
| US6387500B1 (en) | 1997-11-06 | 2002-05-14 | Cabot Corporation | Multi-layered coatings and coated paper and paperboards |
| US6472471B2 (en) | 1997-12-16 | 2002-10-29 | Cabot Corporation | Polymeric products containing modified carbon products and methods of making and using the same |
| US6103380A (en) | 1998-06-03 | 2000-08-15 | Cabot Corporation | Particle having an attached halide group and methods of making the same |
| JP6224021B2 (en) * | 2015-03-24 | 2017-11-01 | 三菱重工業株式会社 | Method for producing carbon fiber reinforced thermoplastics |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4832993A (en) * | 1971-08-26 | 1973-05-04 | ||
| JPS5040891A (en) * | 1973-08-14 | 1975-04-14 | ||
| JPS53122894A (en) * | 1977-03-30 | 1978-10-26 | Japan Exlan Co Ltd | Treating of carbon fiber |
-
1982
- 1982-10-29 JP JP19035382A patent/JPS5982467A/en active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4832993A (en) * | 1971-08-26 | 1973-05-04 | ||
| JPS5040891A (en) * | 1973-08-14 | 1975-04-14 | ||
| JPS53122894A (en) * | 1977-03-30 | 1978-10-26 | Japan Exlan Co Ltd | Treating of carbon fiber |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5982467A (en) | 1984-05-12 |
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