JPH0319256B2 - - Google Patents
Info
- Publication number
- JPH0319256B2 JPH0319256B2 JP28566485A JP28566485A JPH0319256B2 JP H0319256 B2 JPH0319256 B2 JP H0319256B2 JP 28566485 A JP28566485 A JP 28566485A JP 28566485 A JP28566485 A JP 28566485A JP H0319256 B2 JPH0319256 B2 JP H0319256B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- composite material
- intermediate material
- material according
- epoxy
- 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
Links
- 239000002131 composite material Substances 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229920000728 polyester Polymers 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- 239000004593 Epoxy Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 239000004643 cyanate ester Substances 0.000 claims description 9
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 8
- 239000012779 reinforcing material Substances 0.000 claims description 8
- 239000011342 resin composition Substances 0.000 claims description 8
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 7
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 claims description 5
- 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 claims description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 4
- 229920003192 poly(bis maleimide) Polymers 0.000 claims description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 3
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229910052814 silicon oxide Inorganic materials 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 claims 1
- JDVIRCVIXCMTPU-UHFFFAOYSA-N ethanamine;trifluoroborane Chemical compound CCN.FB(F)F JDVIRCVIXCMTPU-UHFFFAOYSA-N 0.000 claims 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims 1
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003822 epoxy resin Substances 0.000 description 6
- 229920000647 polyepoxide Polymers 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- -1 aliphatic amines Chemical class 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 3
- 150000002170 ethers Chemical class 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000012669 compression test Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- HMHLDAMOJGEOMQ-UHFFFAOYSA-N (1-cyanato-4-phenylcyclohexa-2,4-dien-1-yl) cyanate Chemical group C1=CC(OC#N)(OC#N)CC=C1C1=CC=CC=C1 HMHLDAMOJGEOMQ-UHFFFAOYSA-N 0.000 description 1
- GUGZCSAPOLLKNG-UHFFFAOYSA-N (4-cyanatophenyl) cyanate Chemical compound N#COC1=CC=C(OC#N)C=C1 GUGZCSAPOLLKNG-UHFFFAOYSA-N 0.000 description 1
- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 1
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- KPOXQAKDFUYNFA-UHFFFAOYSA-N 3-methyl-7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(O)=O)C(C)CC2OC21 KPOXQAKDFUYNFA-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- WRDNCFQZLUCIRH-UHFFFAOYSA-N 4-(7-azabicyclo[2.2.1]hepta-1,3,5-triene-7-carbonyl)benzamide Chemical compound C1=CC(C(=O)N)=CC=C1C(=O)N1C2=CC=C1C=C2 WRDNCFQZLUCIRH-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
- ULPDSNLBZMHGPI-UHFFFAOYSA-N 4-methyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1C(C)CCC2OC21 ULPDSNLBZMHGPI-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 229910002019 Aerosil® 380 Inorganic materials 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- BUPOATPDNYBPMR-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfonylphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1S(=O)(=O)C1=CC=C(OC#N)C=C1 BUPOATPDNYBPMR-UHFFFAOYSA-N 0.000 description 1
- AUYQDAWLRQFANO-UHFFFAOYSA-N [4-[(4-cyanatophenyl)methyl]phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1CC1=CC=C(OC#N)C=C1 AUYQDAWLRQFANO-UHFFFAOYSA-N 0.000 description 1
- SIZDMAYTWUINIG-UHFFFAOYSA-N [4-[1-(4-cyanatophenyl)ethyl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)C1=CC=C(OC#N)C=C1 SIZDMAYTWUINIG-UHFFFAOYSA-N 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000001913 cyanates Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- FDPIMTJIUBPUKL-UHFFFAOYSA-N dimethylacetone Natural products CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000012784 inorganic fiber Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011269 tar Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tertâbutyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- JBCJMTUHAXHILC-UHFFFAOYSA-N zinc;octanoic acid Chemical compound [Zn+2].CCCCCCCC(O)=O JBCJMTUHAXHILC-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
- Reinforced Plastic Materials (AREA)
Description
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ãäžããè€åææçšäžéæã«é¢ãããDETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to an intermediate material for composite materials that provides excellent heat resistance, water resistance and mechanical properties.
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Conventionally, various resin compositions have been used as matrices for composite materials, but especially in the field of thermosetting resins, in addition to the excellent mechanical properties of the resin itself (particularly strength and elongation), Epoxy resins have been widely used because they have good adhesive properties and the strength development of reinforcing materials is superior to other thermosetting resins. In recent years, there has been a strong demand for higher performance of composite materials, especially improvements in heat resistance, water resistance, and impact resistance. These pre-reactants are being considered. As a result, although the rigidity of the resin increased and the heat resistance and water resistance of the composite material improved, there were problems with a decrease in elongation and a decrease in impact resistance.
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The present inventors have arrived at the present invention as a result of intensive studies aimed at developing an intermediate material for composite materials having high heat resistance, water resistance, and excellent impact resistance.
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The present invention provides polyfunctional maleimide () and polyfunctional cyanate ester or oligomer thereof ().
mixture of () or pre-reactant of () and () (A)
100 parts by weight, 5 to 100 parts by weight of epoxy compound (B) and general formula (In the formula, Ar is a phenylene group and R 1 is a divalent aliphatic group.) Polyester compound (C)5
This is an intermediate material for composite materials in which a reinforcing material is impregnated with ~50 parts by weight of a resin composition.
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ããåºïŒâCH2ïŒâ2ãïŒâCH2ïŒâ3ãâCH2âCHïŒCH3ïŒ
âãCHâC2H5ãïŒâCH2ïŒâ4ãâCH2âCH
ïŒCH3ïŒâCH2âãïŒâCH2ïŒâ5ãïŒâCH2ïŒâ3CH
ïŒCH3ïŒâãïŒâCH2ïŒâ2CHïŒCH3ïŒâCH2âãïŒâCH2
ïŒâ2CHïŒC2H5ïŒâãâCH2âïŒCH3ïŒ2âCH2âçã Substituent in polyester compound (C) of formula (1)
The phenylene group for Ar may be any o-phenylene group, m-phenylene group, or p-phenylene group, and the divalent aliphatic group for R 1 may be a straight C2-C6 aliphatic group. A chain or branched aliphatic group is preferred, and examples include the following groups. Group ( -CH2 ) -2 , ( -CH2 ) -3 , -CH2 -CH( CH3 )
â, CHâC 2 H 5 , (âCH 2 )â 4 , âCH 2 âCH
( CH3 ) âCH2â , ( âCH2 ) â5 , ( âCH2 ) â3 CH
(CH 3 )â, (âCH 2 )â 2 CH(CH 3 )âCH 2 â, (âCH 2
) -2CH ( C2H5 )-, -CH2 - C ( CH3 ) 2 - CH2- , etc.
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ã¢ãããžããšãã«ãšãŒãã«çãçšããããã Polyfunctional maleimide () used in the present invention
is a compound having two or more maleimide groups, and has the general formula In addition to bismaleimide represented by the formula (in which R 2 represents a divalent aromatic group or aliphatic group), it also includes prepolymers obtained from these bismaleimides and diamines. The bismaleimide of formula (2) can be produced by a known method of preparing bismaleamic acid by reacting maleic anhydride with a diamine, and then cyclodehydrating it. As the diamine, aromatic diamines are preferred from the viewpoint of heat resistance, but aliphatic amines may be used alone or in combination if it is desired to impart functions such as flexibility. Examples of diamines include m-phenylenediamine, p-phenylenediamine 4,4'-diaminodiphenylsulfone, 3,3'-diaminodiphenylsulfone,
4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl ether, etc. are used.
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ãããã The polyfunctional cyanate ester () used in the present invention is an organic compound having two or more cyanate ester groups and an oligomer thereof, and has the general formula R 3 (-0-Câ¡N) o (3) ( In the formula, n is an integer of 2 to 5, and R 3 represents an aromatic organic residue. Examples of polyfunctional cyanate esters include 1,3- or 1,4-dicyanatobenzene, 4,4-dicyanatobiphenyl, bis(4-cyanatophenyl)methane, and 2,2-bis( 4-cyanatophenyl)ethane, 2,2-bis(4-cyanatophenyl)propane, bis(4-cyanatophenyl)sulfone, etc. are used. The polyfunctional cyanate ester described above can be used in the form of a triazine oligomer obtained by trimerizing cyanate, or in the form of a prepolymer obtained by reaction with an amine. and those used for metamorphosis.
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å¿ããŠé©å®éžæ䜿çšãããã In the present invention, as component A, a mixture of the polyfunctional maleimide () and a polyfunctional cyanate ester or its oligomer (), or a mixture obtained by pre-reacting () with () in the absence or presence of a catalyst, is used. Preliminary reactants are appropriately selected and used depending on the purpose.
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ãã The epoxy compound (B) used in the present invention may be any known epoxy resin, such as the following compounds. Polyglycidyl ethers of diphenylolalkanes such as diphenylopropane, diphenyloethane, and diphenylomethane; polyglycidyl ethers of polyhydric phenols such as novolac, cresol, and resol; cyclohexane, cyclopentadiene, dicyclopentadiene, etc. Epoxy resins produced by epoxidation of alicyclic compounds, such as (3,4-epoxy-6-methyl-cyclohexane)-methyl ester of 3,4-epoxy-6-methyl-cyclohexane-carboxylic acid, ethylene glycol, glycerin poly(epoxyalkyl)ethers of aliphatic polyoxy compounds such as, epoxyalkyl esters of carboxylic acids such as glycidyl esters of aromatic or aliphatic carboxylic acids, etc. Also, for example, U.S. Patent Nos. 3390037, 2970983, and
It may be a preliminary reaction product of an epoxy resin and a curing agent as described in each specification of No. 3067170,
It may also be a simple mixture. These may be used alone or in combination of two or more. Suitable epoxy compounds include, for example, diglycidyl ether of bisphenol A or diglycidyl ether of bisphenol F, or pre-reacted products of these epoxy compounds and diaminodiphenylsulfone at an epoxy group/NH group ratio of 4/1. Can be mentioned.
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è¬çãªæ¹æ³ã«ãã€ãŠè£œé ã§ããã Polyester compound of formula (1) used in the present invention
(C) is preferably a compound whose acid component is mainly terephthalic acid and whose glycol component is mainly neopentyl glycol or ethylene glycol. The polyester compound used in the present invention must have a softening point of 100°C or lower, preferably 70°C or lower. If the softening point exceeds 100°C, the compatibility with polyfunctional maleimide, polyfunctional cyanate ester, and epoxy compound deteriorates, making it difficult to obtain a uniform composition. This polyester compound has a number average molecular weight of 500~
10,000, particularly preferably 500 to 3,000.
If it is less than 500, the viscosity decreases, and if it exceeds 10,000, it is not suitable because it lacks workability in mixing with other components. The polyester compound used in the present invention can be produced by a general method used in the production of other linear polyesters.
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èç±æ°Žæ§ãäœäžãããã奜ãŸãããªãã The resin composition used in the present invention has an A component of 100%
5 to 100 parts by weight of component B, 5 to 100 parts by weight of component C
It is necessary to set the composition ratio to 50 parts by weight. If the amount of the epoxy compound used as component B is less than 5 parts by weight, the adhesion to the substrate will be poor, and if it exceeds 100 parts by weight, satisfactory heat resistance will not be obtained. Also C
If the amount of the component polyester compound used is less than 5 parts by weight, sufficient impact resistance will not be exhibited.
If it exceeds 50 parts by weight, heat resistance and solvent resistance will be significantly reduced. The ratio of ()/() in component A is preferably 5-15/95-85. If the amount of polyfunctional maleimide () is more than 15, heat resistance will improve, but a high curing temperature will be required, and impact resistance will decrease, and if it is less than 5, impact resistance will improve, but
This is not preferred because hot water resistance decreases.
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ããããšã奜ãŸããã A catalyst may be added to the resin composition used in the present invention for the purpose of imparting desired properties to the cured resin product or adjusting the thermosetting properties of the resin.
Examples of catalysts include latent curing catalysts such as boron trifluoride amine complexes, triethylenediamine, 1,8-diazabicyclo(5,4,0)undecene, N,N-dimethylbenzylamine, N-
Tertiary amines such as methylmorpholine and tri-n-butylamine, organic peroxides such as dicumyl peroxide, benzoyl peroxide, and t-butyl hydroperoxide, zinc octylate, tin octylate,
Examples include organic acid metal salts such as zinc naphthenate and cobalt naphthenate. The amount of catalyst to be used may be determined depending on the purpose, but from the viewpoint of stability of the resin composition, it is preferably 0.2 to 3% by weight based on the total resin solid components.
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ããããã As the reinforcing material for the intermediate material for composite materials of the present invention,
In addition to inorganic fibers such as glass fiber, carbon fiber, boron fiber, and silicon carbide fiber, chop-shaped, yarn-shaped, and tape-shaped products are made of organic fibers such as poly-p-phenylene terephthalamide, poly-p-benzamide, and polyamide hydrazide. , sheet, knitted, pine, paper, asbestos, mica,
Talc and the like, as well as mixtures of two or more thereof, are used.
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NASA RP1092ã«æºæ ããŠã寞æ³ïŒÃïŒÃ0.25ã€
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ãèœäžãããæ¿åïŒã€ã³ãåœã1500lbin
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æç®å€ã§ãããExample 1 Bis(4-maleimidophenyl)methane, 2,
2-bis(4-cyanatophenyl)propane,
Epikote 807 (manufactured by Schiel Kagaku Co., Ltd.) having an epoxy equivalent of 172 and polyester (a) with a softening point of 25°C consisting of terephthalic acid as an acid component and neopentyl glycol as a glycol component are mixed in the proportions shown in the table below, and a fine amount of silicon oxide is added. 1.25 parts of powder AEROSIL 380 (manufactured by Nippon Aerosil Co., Ltd.) and 0.2 parts of dicumyl peroxide as a curing catalyst were added, and a preliminary reaction was carried out at 70°C for 30 minutes to obtain a prepolymer. This prepolymer is sandwiched between glass plates to a predetermined thickness.
A resin plate was obtained by curing at 180°C for 2 hours. In addition, this prepolymer is dissolved in methyl ethyl ketone, impregnated with carbon fiber (Pyrofil T-3 manufactured by Mitsubishi Rayon Co., Ltd.), wound around a drum, dried, and then cut open to create a unidirectional prepreg (thread density).
145 g/m 2 , resin content 33% by weight). This prepreg was laminated to [0°] 16 , and also [+45°/
0ã/-45ã/+90ã) 4S pseudo-isotropically stacked and heated at 180â
The mixture was cured for 2 hours to obtain a composite material. Various tests were then conducted on resins and composite materials. The results are shown in the table below. The glass transition point (Tg) in the table is the tan Ύ MAX temperature measured with a Dynamik mechanical spectrometer manufactured by Rheometrics. The hot water resistance of the composite material was determined after a 16-layer laminate composite was left in water at 71°C for 14 days.
Judgment was made by performing a compression test in the 0° direction at 121°C in accordance with ASTM D695. In addition, the impact resistance
In accordance with NASA RP1092, a board with dimensions of 4 x 6 x 0.25 inches was fixed on a table with a 3 x 5 inch hole, and a 1/2 inch radius nose was attached in the center.
Dropping a kg weight, 1500lbin per inch of plate thickness
It was determined by applying an impact to the plate and then performing a compression test. All composite data are calculated based on a fiber content of 60%.
å®æœäŸ ïŒ
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åç©ããæãè»åç¹20âã®ããªãšã¹ãã«(b)ãçš
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åæãåŸããå皮詊éšã®çµæãäžèšè¡šã«ç€ºããExample 2 Polyester (b) with a softening point of 20°C consisting of terephthalic acid as the acid component and a 1:1 (by weight) mixture of ethylene glycol and neopentyl glycol as the glycol component was used instead of polyester (a), and the other conditions were as follows. A resin plate and a composite material were obtained in the same manner as in Example 1. The results of various tests are shown in the table below.
å®æœäŸ ïŒ
ãšããã·æš¹èãšããŠããšããã·åœé184ã194ã®
ãšãã³ãŒã828ïŒã·ãšã«ååŠç€Ÿè£œïŒãçšãããã®ä»
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ããè©Šéšçµæãäžèšè¡šã«ç€ºããExample 3 A resin plate and a composite material were obtained in the same manner as in Example 1 except that Epikote 828 (manufactured by Ciel Chemical Co., Ltd.) having an epoxy equivalent of 184 to 194 was used as the epoxy resin. The test results are shown in the table below.
å®æœäŸïŒãæ¯èŒäŸïŒåã³ïŒ
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æãäžèšè¡šã«ç€ºããExample 4, Comparative Examples 1 and 2 A resin plate and a composite material were obtained in the same manner as in Example 1 except that the amount of polyester (a) used was changed. The test results are shown in the table below.
å®æœäŸïŒãæ¯èŒäŸïŒåã³ïŒ
ãšãã³ãŒã807ã®äœ¿çšéãå€ãããã®ä»ã¯å®æœ
äŸïŒãšåæ§ã«ããŠæš¹èæ¿ãšè€åæãåŸããExample 5, Comparative Examples 3 and 4 A resin plate and a composite material were obtained in the same manner as in Example 1 except that the amount of Epicote 807 used was changed.
è©Šéšçµæãäžèšè¡šã«ç€ºãã The test results are shown in the table below.
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ããExamples 6 and 7 Resin plates and composite materials were prepared in the same manner as in Example 1 except that the amounts of bis(4-maleimidophenyl)methane and 2,2-bis(4-cyanatophenyl)propane were changed. Obtained. The test results are shown in the table below.
Claims (1)
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ç¯å²ç¬¬ïŒé ã«èšèŒã®è€åææçšäžéæã ïŒ è§ŠåªãšããŠäžåŒåç¡ŒçŽ ã¢ããšãã«ã¢ãã³é¯
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éæã[Scope of Claims] 1. 100 parts by weight of a mixture of polyfunctional maleimide () and polyfunctional cyanate ester or its oligomer () or a preliminary reaction product (A) of () and (), epoxy compound (B) 5-100 parts by weight and general formula (In the formula, Ar is a phenylene group and R 1 is a divalent aliphatic group) Polyester compound (C)5
An intermediate material for composite materials in which a reinforcing material is impregnated with ~50 parts by weight of a resin composition. 2. The intermediate material for a composite material according to claim 1, wherein the polyfunctional maleimide () is bismaleimide of diaminodiphenylmethane. 3. The intermediate material for a composite material according to claim 1, wherein the polyfunctional cyanate ester () is dicyanate of bisphenol A. 4. The epoxy compound (B) is diglycidyl ether of bisphenol A or diglycidyl ether of bisphenol F, or a preliminary reaction product of these epoxy compounds and diaminodiphenylsulfone at an epoxy group/NH group ratio of 4/1. An intermediate material for a composite material according to claim 1, characterized in that: 5 The polyester compound (C) is a reaction product from terephthalic acid and neopentyl glycol, has a softening temperature of 100°C or less, and has an average molecular weight of 500~
10,000, the intermediate material for composite material according to claim 1. 6. The intermediate material for a composite material according to claim 1, which contains 0.2 to 3% by weight of silicon oxide fine powder. 7 The weight ratio of ()/() in component A is 5 to
15/95-85, the intermediate material for composite material according to claim 1. 8. The intermediate material for a composite material according to claim 1, which contains 0.2 to 3% by weight of boron trifluoride monoethylamine complex, dicumyl peroxide and/or zinc octylate as a catalyst. .
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28566485A JPS62146927A (en) | 1985-12-20 | 1985-12-20 | Intermediate for composite material |
DE8686117763T DE3673150D1 (en) | 1985-12-20 | 1986-12-19 | INTERMEDIATE PRODUCT FOR COMPOSITE MATERIALS. |
EP19860117763 EP0230631B2 (en) | 1985-12-20 | 1986-12-19 | Intermediate for composite material |
ES86117763T ES2016249T5 (en) | 1985-12-20 | 1986-12-19 | PROCEDURE FOR PREPARING AN INTERMEDIATE FOR A COMPOSITE MATERIAL. |
US07/320,803 US5003013A (en) | 1985-12-20 | 1989-03-09 | Intermediate for composite of polymaleimide, polycyanate, epoxy resin and polyester |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP28566485A JPS62146927A (en) | 1985-12-20 | 1985-12-20 | Intermediate for composite material |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS62146927A JPS62146927A (en) | 1987-06-30 |
JPH0319256B2 true JPH0319256B2 (en) | 1991-03-14 |
Family
ID=17694456
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP28566485A Granted JPS62146927A (en) | 1985-12-20 | 1985-12-20 | Intermediate for composite material |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS62146927A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6330558A (en) * | 1986-07-25 | 1988-02-09 | Yokohama Rubber Co Ltd:The | Thermosetting resin composition |
US6534179B2 (en) | 2001-03-27 | 2003-03-18 | International Business Machines Corporation | Halogen free triazines, bismaleimide/epoxy polymers, prepregs made therefrom for circuit boards and resin coated articles, and use |
JP5016998B2 (en) * | 2007-07-03 | 2012-09-05 | äžè±ã¬ã€ãšã³æ ªåŒäŒç€Ÿ | Matrix resin and prepreg for fiber reinforced composite materials |
JP2012131948A (en) * | 2010-12-24 | 2012-07-12 | Sumitomo Bakelite Co Ltd | Resin composition, prepreg, laminate plate, resin sheet, printed wiring board, and semiconductor device |
CN105542128A (en) * | 2015-12-15 | 2016-05-04 | 广äžå¹¿å±±æ°æææéå ¬åž | Curing agent for epoxy resin as well as preparation method and application thereof |
JP6354884B1 (en) * | 2017-03-13 | 2018-07-11 | 暪æµãŽã æ ªåŒäŒç€Ÿ | Cyanate ester resin composition and prepreg |
CN110655791B (en) * | 2019-09-30 | 2022-03-01 | èŸèç¹æéœæ°ææç§ææéå ¬åž | High heat-resistant low-dielectric active ester resin composition and preparation method of laminated board |
-
1985
- 1985-12-20 JP JP28566485A patent/JPS62146927A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS62146927A (en) | 1987-06-30 |
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