JPH0317153A - New heat-resistant and solvent-resistant resin composition - Google Patents
New heat-resistant and solvent-resistant resin compositionInfo
- Publication number
- JPH0317153A JPH0317153A JP14944989A JP14944989A JPH0317153A JP H0317153 A JPH0317153 A JP H0317153A JP 14944989 A JP14944989 A JP 14944989A JP 14944989 A JP14944989 A JP 14944989A JP H0317153 A JPH0317153 A JP H0317153A
- Authority
- JP
- Japan
- Prior art keywords
- polyphenylene ether
- polyphenylene
- modified
- polyphenylene sulfide
- ether
- 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
- 239000002904 solvent Substances 0.000 title claims abstract description 20
- 239000011342 resin composition Substances 0.000 title claims abstract description 7
- 229920001955 polyphenylene ether Polymers 0.000 claims abstract description 40
- 239000004734 Polyphenylene sulfide Substances 0.000 claims abstract description 32
- 229920000069 polyphenylene sulfide Polymers 0.000 claims abstract description 32
- 229920005989 resin Polymers 0.000 claims abstract description 9
- 239000011347 resin Substances 0.000 claims abstract description 9
- 239000003607 modifier Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004018 acid anhydride group Chemical group 0.000 claims description 4
- 238000012986 modification Methods 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- -1 polyphenylene Polymers 0.000 abstract description 26
- 229920001577 copolymer Polymers 0.000 abstract description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 abstract description 12
- 239000000203 mixture Substances 0.000 abstract description 9
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 abstract description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 6
- 229920000265 Polyparaphenylene Polymers 0.000 abstract description 3
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 150000008064 anhydrides Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 238000002156 mixing Methods 0.000 description 12
- 238000000034 method Methods 0.000 description 11
- 239000008188 pellet Substances 0.000 description 11
- 229920001971 elastomer Polymers 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- 239000000835 fiber Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000805 composite resin Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000005060 rubber Substances 0.000 description 3
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 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 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 150000002763 monocarboxylic acids Chemical class 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- IXQGCWUGDFDQMF-UHFFFAOYSA-N o-Hydroxyethylbenzene Natural products CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- DMYOHQBLOZMDLP-UHFFFAOYSA-N 1-[2-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1CCCCN1CC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 DMYOHQBLOZMDLP-UHFFFAOYSA-N 0.000 description 1
- GWWBILGABMLVTN-UHFFFAOYSA-N 1-but-1-enyl-2,3-dimethylbenzene Chemical group CCC=CC1=CC=CC(C)=C1C GWWBILGABMLVTN-UHFFFAOYSA-N 0.000 description 1
- WAEOXIOXMKNFLQ-UHFFFAOYSA-N 1-methyl-4-prop-2-enylbenzene Chemical group CC1=CC=C(CC=C)C=C1 WAEOXIOXMKNFLQ-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- RLEWTHFVGOXXTN-UHFFFAOYSA-N 2,3-diethylphenol Chemical compound CCC1=CC=CC(O)=C1CC RLEWTHFVGOXXTN-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- MTLWTRLYHAQCAM-UHFFFAOYSA-N 2-[(1-cyano-2-methylpropyl)diazenyl]-3-methylbutanenitrile Chemical compound CC(C)C(C#N)N=NC(C#N)C(C)C MTLWTRLYHAQCAM-UHFFFAOYSA-N 0.000 description 1
- CKEUSTRYGVZRLN-UHFFFAOYSA-N 2-[tris(dimethylamino)methyl]phenol Chemical compound CN(C)C(N(C)C)(N(C)C)C1=CC=CC=C1O CKEUSTRYGVZRLN-UHFFFAOYSA-N 0.000 description 1
- OCKYMBMCPOAFLL-UHFFFAOYSA-N 2-ethyl-3-methylphenol Chemical compound CCC1=C(C)C=CC=C1O OCKYMBMCPOAFLL-UHFFFAOYSA-N 0.000 description 1
- XRSWLVYCXFHDDB-UHFFFAOYSA-N 2-ethyl-3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1CC XRSWLVYCXFHDDB-UHFFFAOYSA-N 0.000 description 1
- AKZFZHNJLYDHKN-UHFFFAOYSA-N 2-ethyl-6-propylphenol Chemical compound CCCC1=CC=CC(CC)=C1O AKZFZHNJLYDHKN-UHFFFAOYSA-N 0.000 description 1
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- XNCTZUPZTWUFNW-UHFFFAOYSA-N 2-methyl-3-propylphenol Chemical compound CCCC1=CC=CC(O)=C1C XNCTZUPZTWUFNW-UHFFFAOYSA-N 0.000 description 1
- NXSQQKKFGJHACS-UHFFFAOYSA-N 2-methyl-6-propylphenol Chemical compound CCCC1=CC=CC(C)=C1O NXSQQKKFGJHACS-UHFFFAOYSA-N 0.000 description 1
- IVFJPARIJHUGPZ-UHFFFAOYSA-N 3-ethyl-2-methylphenol Chemical compound CCC1=CC=CC(O)=C1C IVFJPARIJHUGPZ-UHFFFAOYSA-N 0.000 description 1
- RIAHASMJDOMQER-UHFFFAOYSA-N 5-ethyl-2-methyl-1h-imidazole Chemical compound CCC1=CN=C(C)N1 RIAHASMJDOMQER-UHFFFAOYSA-N 0.000 description 1
- QMZCVQNGASCJAX-UHFFFAOYSA-N 5-methyl-3-propyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(CCC)=CC2=C1 QMZCVQNGASCJAX-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- 241000951471 Citrus junos Species 0.000 description 1
- 241000219112 Cucumis Species 0.000 description 1
- 235000015510 Cucumis melo subsp melo Nutrition 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- 229920001079 Thiokol (polymer) Polymers 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000005083 Zinc sulfide Substances 0.000 description 1
- FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- FJMNNXLGOUYVHO-UHFFFAOYSA-N aluminum zinc Chemical compound [Al].[Zn] FJMNNXLGOUYVHO-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- PVEOYINWKBTPIZ-UHFFFAOYSA-N but-3-enoic acid Chemical compound OC(=O)CC=C PVEOYINWKBTPIZ-UHFFFAOYSA-N 0.000 description 1
- 229920005549 butyl rubber Polymers 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
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- 239000011152 fibreglass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 238000009863 impact test Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 150000002506 iron compounds Chemical class 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
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- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- 239000011490 mineral wool Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 229920003225 polyurethane elastomer Polymers 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012779 reinforcing material Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910052984 zinc sulfide Inorganic materials 0.000 description 1
- DRDVZXDWVBGGMH-UHFFFAOYSA-N zinc;sulfide Chemical compound [S-2].[Zn+2] DRDVZXDWVBGGMH-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は高耐熱性、成形性、耐溶剤性、に侵れた新規々
樹′ａ組戊物に係わり、さらに詳細には＾｝ポリフェニ
レンエーテルを分子中に（ａ）エチレン性二重結合と（
ｂ）カルポキシル基または酸無水物基を有する有機化合
物から選ばれた変性剤でラジカル開始剤の存在下又は非
存在下に変性して得られる変性ポリフェニレンエーテル
とＣＢＩポリフェニレンスルフィドからなる、新規な耐
熱性、耐溶剤性樹指４２１戊物に係わる。[Detailed Description of the Invention] [Field of Industrial Application] The present invention relates to a novel composite material having high heat resistance, moldability, and solvent resistance, and more specifically relates to a novel composite material made of polyphenylene. The ether has (a) an ethylenic double bond and (
b) A novel heat-resistant product consisting of modified polyphenylene ether and CBI polyphenylene sulfide obtained by modifying with a modifier selected from organic compounds having a carpoxyl group or an acid anhydride group in the presence or absence of a radical initiator. , related to solvent-resistant resin 421 wood.
ボＩＪ ７エニレンエーテルは、耐熱性、剛性、電気特
性等に秀でた樹脂であり、エンジニアリングプラスチッ
クとして有用な高分子材料である。しかしながら、ポリ
フェニレンエーテルは耐溶剤性に劣り、さらには、威形
加工性が悪いという大きな欠点を有することはよく知ら
れている。Bo IJ 7 enylene ether is a resin with excellent heat resistance, rigidity, electrical properties, etc., and is a polymer material useful as an engineering plastic. However, it is well known that polyphenylene ether has major drawbacks such as poor solvent resistance and poor shapeability.
一方、ポリフェニレンスルフィドは、耐熱性、耐溶剤性
、電気特性、機械的強度、寸法安定性、難燃性等が優れ
た慟脂として知られており、近年注目されている。特に
ポリフエニレンスルフィドは、ガラス偵維、炭素繊維扛
どの４８維状強化材、タルク、クレー、シリカなどの無
機質充填材との複合化により上記性能を向上させること
ができ、電気、電子部品、機械構造部品等に使用されて
いる。しかしｔｌがら、ポリフエニレンスルフィドは重
合度が低く、成形加工が困難で靭性が？！＜ｉい、又ガ
ラス繰帷で強化されたポリフェニレンスルフィドは成形
品にソリが生じやすいなどの欠点を有する。On the other hand, polyphenylene sulfide is known as a resin with excellent heat resistance, solvent resistance, electrical properties, mechanical strength, dimensional stability, flame retardancy, etc., and has attracted attention in recent years. In particular, polyphenylene sulfide can improve the above performance by combining it with 48 fibrous reinforcing materials such as glass fibers and carbon fibers, and inorganic fillers such as talc, clay, and silica. Used in mechanical structural parts, etc. However, polyphenylene sulfide has a low degree of polymerization, is difficult to mold, and has poor toughness. ! In addition, polyphenylene sulfide reinforced with glass fiber has drawbacks such as warpage in molded products.
ボリフェニレンエーテルの成形加工性を改良するための
技術としては、例えば特公昭５６一３４０３２号でポリ
フェニレンスルフィドをブレンドすることが開示されて
いる。しかしながら、成形加工性の改善効果は見られる
ものの、ポリフェニレンエーテルとポリフェニレンスル
フィドとの相溶性が乏しい為、外校不良、機械的性質の
低下などの問題点を有していた。As a technique for improving the moldability of polyphenylene ether, blending polyphenylene sulfide is disclosed, for example, in Japanese Patent Publication No. 56-134032. However, although the effect of improving molding processability was observed, the compatibility between polyphenylene ether and polyphenylene sulfide was poor, resulting in problems such as defective molding and deterioration of mechanical properties.
またポリフェニレンエーテルとポリフェニレンスルフィ
ドとの相溶性を改善するための技術として、エポキシ樹
脂を介在させることが特公昭６０−１１０６３号公報に
開示されている。Further, as a technique for improving the compatibility between polyphenylene ether and polyphenylene sulfide, interposition of an epoxy resin is disclosed in Japanese Patent Publication No. 11063/1983.
しかしながら、相溶性の改善効果はある程度見られるも
のの十分ではなく、機械的性質、耐溶剤性なども満足す
べきものではなかった。However, although the compatibility was improved to some extent, it was not sufficient, and the mechanical properties, solvent resistance, etc. were also unsatisfactory.
また、ポリフェニレンエーテルを無水マレイン酸で変性
し、ポリフェニレンスルフィドとの相溶性を改善するた
めの技術が、特開昭６４−３６６４５号公報に示されて
いるが、相溶性の改善効果は見られるものの十分でなく
、耐衝撃性、耐溶剤性もまだ満足すべきものではない。Furthermore, a technique for modifying polyphenylene ether with maleic anhydride to improve its compatibility with polyphenylene sulfide is disclosed in JP-A-64-36645, but although the effect of improving compatibility is seen, The impact resistance and solvent resistance are still unsatisfactory.
本発明が目的とした解決すべき問題点は、ポリフェニレ
ンエーテルとポリフェニレンスルフィドをブレンドした
時に両者の本質的相溶性不良に起因する材料の耐ｆｆｒ
撃性、耐溶剤性の低下を防止することにある。The problem to be solved by the present invention is that when polyphenylene ether and polyphenylene sulfide are blended, the ffr resistance of the material is due to the inherent poor compatibility between the two.
The objective is to prevent deterioration of impact resistance and solvent resistance.
この点の解決により従来技術には見られない機械的性能
、耐衝撃性、耐溶剤性に優れ、かつ耐熱性、成形性にも
優れた材料の創出が可能となった。By solving this problem, it has become possible to create a material that has excellent mechanical performance, impact resistance, and solvent resistance, as well as excellent heat resistance and moldability, which were not found in the prior art.
すなわち本発明は、（Ａｌポリフェニレンエーテルを分
子中に−｝エチレン性二重結合と←）カルボキシル基ま
たは酸無水物基から選ばれる官能基を有する有機化合物
から選ばれた変性剤でラジカル開始剤の存在下又は非存
在下に変性して得られる変性ポリフェニレンエーテルと
， （Ｂｌｓ Ｈ末端基の濃度が樹脂Ｉ Ｋ９につき１
０ミリグラム当量以上である、ポリフェニレンスルフィ
ドからなる新規な耐熱性、耐溶剤性樹脂組成物である。That is, the present invention provides a radical initiator using a modifier selected from organic compounds having (-}ethylenic double bonds and ←) carboxyl groups or acid anhydride groups in the molecule of Al polyphenylene ether. Modified polyphenylene ether obtained by modification in the presence or absence of (Bls H end group concentration 1 per resin I K9)
This is a novel heat-resistant and solvent-resistant resin composition composed of polyphenylene sulfide having a weight of 0 milligram equivalent or more.
本発明の樹脂組我物において用いられるポリフェニレン
エーテルとは，一般式１（Ｉ）で示される単環式フェノ
ールの一種以上を重箱合して得ら（ここに、Ｒ１ は
炭素数１〜３の低級アルキル基、Ｒ２ およびＲ３
は水素原子または炭素数１〜３の低級アルキル基であり
、水酸基の少なくとも一方のオルト位には必ず低級アル
キル置換基が存在しなければならない。）レンエーテル
にビニル芳香族化合物をグラフト重合して得られる根幹
にボリフェニレンエーテルを有するグラフト共重合体を
包含する。このポリフェニレンエーテルは、単独重合体
であっても共重合体であってもよい。The polyphenylene ether used in the resin composition of the present invention is obtained by combining one or more monocyclic phenols represented by general formula 1(I) (herein, R1 has 1 to 3 carbon atoms). lower alkyl group, R2 and R3
is a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, and a lower alkyl substituent must always be present at the ortho position of at least one of the hydroxyl groups. ) It includes a graft copolymer having polyphenylene ether as its core, which is obtained by graft polymerizing a vinyl aromatic compound to rene ether. This polyphenylene ether may be a homopolymer or a copolymer.
前記一般式（Ｉ＋で示される単環式フェノールとしては
、例えば、２．６−ジメチルフェノール、２．６−ジエ
チルフェノール．２．６−ジプロピルフェノール、２−
メチル−６−エチルフェノール、２−メチル−６−プロ
ビルフェノール、２−エチル−６−プロビルフェノール
、ｍ−クレゾール、２．３−ジメチルフェノール、２，
３−ジエチルフェノール、２．３−ジプロビルフェノー
ル、２−メチル−３−エチルフェノール、２−メチル−
３−プロビルフェノール、２一エチル−３−メチルフェ
ノール、２−エチル−３−プロビルフェノール、２−プ
ロビル−３−メチルフェノール、２−プロビル−３−エ
チルフェノール、２．３．６−｝リメチルフエノ一ル、
２，３．６−｝リエチルフェノール、２．３．６−トリ
プロビルフェノール、２．６−ジメチル−３−エチルー
フェノール，２．６−ジメチル−３−プロビルフェノー
ル等が挙げられる。そして、これらのフェノールの一種
以上の重縮合により得られるポリフェニレンエーテルと
しては、例えば、ポリ（２．６−ジメチルー１．４−フ
ェニレン）エーテル、ポリ （２．６−シエチル−１．
４−フェニレン）エーテル、ポリ （２．６−ジプ
ロビル−１，４−フェニレン）エーテル、ポリ（２−メ
チル−６−エチル−１．４−フェニレン）エーテル、ポ
リ （２一メチル−６−プロビル−１．４−フェニレン
）エーテル、ポリ（２−エチル−６−プロビル−１．４
−フェニレン）エーテル、２．６−ジメチルフェノール
／２．３．６−トリメチルフェノール共ｆｆｉ合体、２
ｔ ６−ジメチルフェ／−ル／２． ３． ６−
｝リエチルフェ／−ル共重合体、２．６−ジエチルフェ
ノール／２，３．６−トリメチルフェノール共ｍ．＝体
、２．６−ジプロビルフェノール／２．３．６−トリメ
チルフェノール共重合体、ポリ（２．６−ジメチル−１
，４−フェニレン）エーテルにスチレンをグラフト重合
したグラフト共重合体、２＃６−ジメチルフェノール／
２．３．６−トリメチルフェノ・−ル共重合体にスチレ
ンをグラフト重合したグラフト共重合体等が挙げられる
。Examples of the monocyclic phenol represented by the general formula (I+) include 2.6-dimethylphenol, 2.6-diethylphenol, 2.6-dipropylphenol, 2-
Methyl-6-ethylphenol, 2-methyl-6-propylphenol, 2-ethyl-6-propylphenol, m-cresol, 2,3-dimethylphenol, 2,
3-diethylphenol, 2,3-diprobylphenol, 2-methyl-3-ethylphenol, 2-methyl-
3-propylphenol, 2-ethyl-3-methylphenol, 2-ethyl-3-propylphenol, 2-propyl-3-methylphenol, 2-propyl-3-ethylphenol, 2.3.6-} Limethylphenol,
Examples thereof include 2,3.6-}ethylphenol, 2.3.6-triprobylphenol, 2.6-dimethyl-3-ethylphenol, and 2.6-dimethyl-3-probylphenol. Examples of polyphenylene ether obtained by polycondensation of one or more of these phenols include poly(2,6-dimethyl-1,4-phenylene) ether, poly(2,6-ethyl-1.
4-phenylene) ether, poly (2,6-dipropyl-1,4-phenylene) ether, poly (2-methyl-6-ethyl-1,4-phenylene) ether, poly (2-methyl-6-propyl- 1.4-phenylene)ether, poly(2-ethyl-6-probyl-1.4)
-phenylene) ether, 2.6-dimethylphenol/2.3.6-trimethylphenol co-ffi combination, 2
t 6-dimethylphenol/2. 3. 6-
}Ethyl phenol/-ethyl phenol copolymer, 2,6-diethyl phenol/2,3,6-trimethyl phenol copolymer, m. = body, 2.6-dipropylphenol/2.3.6-trimethylphenol copolymer, poly(2.6-dimethyl-1
, 4-phenylene) ether grafted with styrene, 2#6-dimethylphenol/
Examples include graft copolymers in which styrene is graft-polymerized to 2.3.6-trimethylphenol copolymer.
これらのポリフェニレンエーテルの中で好ましいものは
、ポリ（２．６−ジメチル−１，４一フェニレン）エー
テル、２．６−ジメチルフェノール／２．３．６−｝リ
メチルフェノール共重合体であり、最も好ましいものは
、２．６−ジメチルフェノール／２，３．６−｝リメチ
ルフェノール共重合体である。Preferred among these polyphenylene ethers are poly(2,6-dimethyl-1,4-phenylene) ether, 2,6-dimethylphenol/2.3.6-}limethylphenol copolymer, The most preferred is 2,6-dimethylphenol/2,3.6-}limethylphenol copolymer.
ポリフェニレンエーテルの 「変性剤」は分子中にー）
エチレン性二重結合と（ｂ）カルボキシル基、または酸
無水物基を有する有機化合物であり、具体的にはマレイ
ン酸、クロロマレイン酸、シトラコン酸、イタコン酸等
で例示されるα．β−不飽和ジカルポン酸；アクリル酸
、プラン酸、クロトン酸、ビニル酢酸、メタクリル酸、
ヘンテン酸、アンゲリカ酸等で例示される不飽和モノカ
ルボン酸；これらのα，β一不飽和ジヵルボン酸わよび
不飽和モノカルボン酸の酸無水物を挙げることができる
。The “modifier” of polyphenylene ether is in the molecule.)
It is an organic compound having an ethylenic double bond and (b) a carboxyl group, or an acid anhydride group, and is specifically an α. β-unsaturated dicarboxylic acid; acrylic acid, puranic acid, crotonic acid, vinylacetic acid, methacrylic acid,
Examples include unsaturated monocarboxylic acids such as henthenic acid and angelic acid; α,β-monounsaturated dicarboxylic acids and acid anhydrides of these unsaturated monocarboxylic acids.
これらの中で好ましいものは、マレイン酸、アクリル酸
、メタクリル酸、無水マレイン酸であり、さらに好まし
いものは無水マレイン酸である。Among these, preferred are maleic acid, acrylic acid, methacrylic acid, and maleic anhydride, and more preferred is maleic anhydride.
本発明で用いられる変性ポリフェニレンエーテルの調製
は、次のような方法によって行なうが、特にこれに限定
されるものではない。たどえば、変性ポリフェニレンエ
ーテルは、前記ボリフェニレンエーテルと変性剤とをロ
ールミル、バンバリーミキサー、押出機等を用いて１５
０〜３５０゜Ｃの温度で溶融混練し、反応させることに
よって調製しても、ベンゼン、トルエン、キシレン、等
で例示される溶媒中でポリフェニレンエーテルと変性剤
とを加熱、反応させることによって調製してもよい。変
性反応を容易に進めるために、反応系にペンゾイルバー
オキサイド、ジーｔ−プチルバーオキサイド、ジクミル
パーオキサイド、ｔ−プチルバーオキシベンゾエート等
で例示される有機過酸化物やアゾビスイソブチロニトリ
ル、アゾビスイソバレロニトリル等で例示されるアゾ化
合物で代表されるラジカル開始剤を存在させることは、
有効である。より有用的な変性方法は、ラジカル開始剤
の存在下に溶！％！ｋ混棟する方法である。The modified polyphenylene ether used in the present invention is prepared by the following method, but is not particularly limited thereto. For example, modified polyphenylene ether can be obtained by mixing the polyphenylene ether and a modifier using a roll mill, Banbury mixer, extruder, etc.
It can be prepared by melt-kneading and reacting at a temperature of 0 to 350°C, or it can be prepared by heating and reacting polyphenylene ether and a modifier in a solvent such as benzene, toluene, xylene, etc. It's okay. In order to facilitate the modification reaction, organic peroxides such as penzoyl peroxide, di-t-butyl peroxide, dicumyl peroxide, t-butyl peroxide, and azobisisobutyronitrile are added to the reaction system. The presence of a radical initiator represented by an azo compound exemplified by azobisisovaleronitrile, etc.
It is valid. A more useful modification method is dissolution in the presence of a radical initiator! %! This is a mixed building method.
次に本発明で用いられるポリフェニレンスルる繰返し単
位を７０モル％以上、より好ましくは９０モル％以上含
む重合体であり、上記繰返し単位が７０モル％未満では
特ａの性質を有する組成物は？８１！い。この重合体を
得る重合方法としては公知の種々の方法を採用し得るが
、硫化ナトリウムとｐ−ジクロノレベンゼンとをＮ−メ
チルビロリドン、ジメチルアセトアミドなどのアミド系
溶媒やスルホランなどのスルホン系溶媒中で反応させる
方法が好適である。この際に重合度を調節するために酢
酸ナトリウム、酢酸リチウム１１どのアルカリ金属カル
ポン酸塩を添加することは好ましい方法である。共重合
或分として３０モル％未満であって、重合体の結晶性に
影響を与えない範囲で、メタ結合ｔ１どを含有していて
もよいが、好ましくは共重合成分は１０モル％未満がよ
い。Next, which is a polymer containing 70 mol% or more, more preferably 90 mol% or more, of polyphenylene repeating units used in the present invention, and which has the property specified in a when the repeating unit is less than 70 mol%? 81! stomach. Various known methods can be used to obtain this polymer, but sodium sulfide and p-dichronolebenzene are mixed in an amide solvent such as N-methylpyrrolidone or dimethylacetamide or a sulfone solvent such as sulfolane. A reaction method is preferred. At this time, it is a preferable method to add an alkali metal carboxylate such as sodium acetate or lithium acetate 11 to adjust the degree of polymerization. The copolymerization component may contain less than 30 mol% of meta bonds, etc., as long as it does not affect the crystallinity of the polymer, but preferably the copolymerization component is less than 10 mol%. good.
ポリフェニレンスルフィドの末端基は、そのが、末端基
に−ＳＨ 基を導入することにより、驚くべきことに
、飛躍的に耐衝撃性、耐溶剤性などが改善されることが
わかった。Surprisingly, it has been found that impact resistance, solvent resistance, etc. can be dramatically improved by introducing -SH groups into the terminal groups of polyphenylene sulfide.
ＳＨ基を導入する方法としては、種々の方法が考えられ
るが、特に限定することなく、示せば、ボリフエニレン
スルフィド合成の最後の段階で塩酸で処理する。あるい
は、精製されたボリフェニレンスルフィドを塩酸のアセ
トン溶媒で処理する。など簡便にＳ Ｈ基を末端に導入
できる。Various methods can be considered for introducing the SH group, but there are no particular limitations, and one example is treatment with hydrochloric acid in the final step of polyphenylene sulfide synthesis. Alternatively, purified polyphenylene sulfide is treated with hydrochloric acid in acetone solvent. A S H group can be easily introduced at the terminal.
さらに、ポリフェニレンスルフィドのＳＨ末端基の濃度
は、樹脂Ｉ Ｋ９につき１０ミリグラム当量以上が好ま
しい。さらに好ましくは、２０ミリグラム当量以上、さ
らに好ましくは３０ミリグラム当量以上である。なおボ
リフェニレンスルフィドのＳＩ｛末端基濃度が川脂１ベ
クにつき１０ｔリグラム当量未満の場合には組成物とし
た場合、耐衝撃性、６４＃剤性の改善が不十分となり好
ましくない。Further, the concentration of SH end groups of polyphenylene sulfide is preferably 10 milligram equivalents or more per resin I K9. More preferably, it is 20 milligram equivalents or more, and even more preferably 30 milligram equivalents or more. It should be noted that if the SI{terminal group concentration of polyphenylene sulfide is less than 10 gram equivalents per 1 vector of river fat, the impact resistance and 64# agent properties will not be sufficiently improved when used as a composition, which is not preferable.
次に本発明の或分（Ａｌ、（Ｂ）の配合ｑは、体）変性
ポリフェニレンエーテル ５〜９５ｆｆｉｆｆｉ％、好
ましくは２０〜８０重漬％、およびμｓ）ボリフエニレ
ンスルフィド ９５〜５重量％、好マシ＜は８０〜２０
重ｆｆｌ％である。ポリフェニレンスルフィドがこの量
より少ないと耐溶剤性、成形性が不十分となり、多すぎ
るとフィラー非強化の場合の耐熱性が低下し、さらには
成形品にソリが生じやすくなる。Next, the composition q of (Al, (B)) of the present invention is a) modified polyphenylene ether 5 to 95 ffiffi%, preferably 20 to 80 ffiffi%, and μs) polyphenylene sulfide 95 to 5 wt%, Better than 80-20
Heavy ffl%. If the amount of polyphenylene sulfide is less than this amount, the solvent resistance and moldability will be insufficient, and if it is too much, the heat resistance in the case of non-reinforced filler will decrease, and furthermore, the molded product will be more likely to warp.
また本発明の樹脂組或物には両成分間の反応を促進する
ために、トリーｎ−プチルアミン、トリフェニルアミン
、ペンジルメチルアミン、トリス（ジメチルアミノ）メ
チルフェノール等の三級アミン：トリエチルベンジルア
ンモニウムクロライド、テトラメチルアンモニウｌ・ク
ロライド等の四級アンモニウム塩；２−メチル−４−エ
チルイミダゾール、２−メチルーイミダゾール等のイミ
ダゾール化合物に代表される触媒を添加することができ
る。In addition, the resin composition of the present invention contains a tertiary amine such as tri-n-butylamine, triphenylamine, pendylmethylamine, tris(dimethylamino)methylphenol, etc., in order to promote the reaction between both components. Catalysts typified by quaternary ammonium salts such as ammonium chloride and tetramethylammonium chloride; and imidazole compounds such as 2-methyl-4-ethylimidazole and 2-methyl-imidazole can be added.
さらに本発明の樹脂組戊物を構成する両叔分の配合方法
は特に限定されないものであるが、両成分をミキサー等
で混合後、押出機、二−ダー等で２５０〜３５０℃の温
度で溶融混榛する等の方法による。Further, the method of blending the two components constituting the resin composite of the present invention is not particularly limited, but after mixing both components in a mixer or the like, the mixture is heated at a temperature of 250 to 350°C in an extruder, seconder, or the like. By methods such as melting and mixing.
本発明の樹脂組戊物には、所望に応じて、他の樹脂：エ
ラストマー：難燃剤：＠燃助剤、安定剤，紫外線吸収剤
、可曖剤、滑剤などの各種添加剤；顔料、充填剤、その
他の成分が適宜配合され得る。The resin composite of the present invention may contain other resins, elastomers, flame retardants, various additives such as combustion aids, stabilizers, ultraviolet absorbers, opaque agents, lubricants, pigments, and fillers, as desired. agents and other ingredients may be appropriately blended.
他の樹脂の例としては、たとえばボリスチレン系樹脂、
ポリカーボネート、ポリエステル、ポリアミド、ポリス
ルホン等が挙げられる。Examples of other resins include polystyrene resin,
Examples include polycarbonate, polyester, polyamide, polysulfone, and the like.
前記エラストマー成分とは、一般的１１意味でのエラス
トマーであり、例えばＡ ， Ｖ ， Ｔｈｂｏｌｓｋ
ｙ著“Ｐｒｏｐｅｒｔｉｅｓ ａｎｄ Ｓｔｒｕｃｔｕ
ｒｅｓ ｏｆ Ｐｏｌｙ −ｒｒｅｒｓ” （Ｊｏｈ
ｎ ％ｌｅｙ ＆ Ｓｏｎｓ，Ｉｎｃ．， １９５
Ｑ年）７１〜７８ページに採用された定義を引用でき、
エラストマーとは常温に於けるヤング率が１０５〜１０
ｄｙｎｅｓ／ｃＰＩ （０− １〜１ ０ ２
０Ｋｑ／ｍ）である重合体を意味する。エラストマーの
具体例としては、Ａ−Ｂ−Ａ’型エラストマー状ブロ，
ク共重合体、ポリブタジエン部分の二重結合が水素添加
されたＡ−Ｂ−Ａ／型エラストマー状ブロック共重合体
、ポリブタジエン、ポリイソプレン、ジエン化合物とビ
ニル芳香族化合物との共重合体、ニトリルゴム、エチレ
ンープロビレン共重合体、エチレンープロピレンージェ
ン共重合体（ＥＰＤＭ），チオコールゴム、ポリスルフ
ィドゴム、アクリル酸ゴム、ポリウレタンゴム、ブチル
ゴムとポリエチレンとのグラフト物，ポリエステルエラ
ストマー、ポリアミドエラストマー等が挙げられる。と
りわけ、Ａ−Ｂ−Ａ／型エラストマー状ブロック共重合
体が望ましい。このブロック共重合体の末端ブロックＡ
およびＡ′は重合されたビニル系芳香族炭化水素ブロッ
クであり、Ｂは重合された共役ジエンブロック或いは二
重結合の大部分が水素添加された共役ジエンブロックで
あり、Ｂブロックの分子量はＡおよびＡ′ブロックの組
み合わされた分子屋よりも大であることが望ましい。末
端ブロックＡおよびＮは同一でも異なってもよく、かつ
該ブロックは、芳香族部分が単環でも多環でもよいビニ
ル芳香族化合物から誘導された熱可塑性単独重合体また
は共重合体である。かかるビニル芳香族化合物の例は、
スチレン、αーメチノレスチレン、ビニルトノレエン、
ビニルキシレン、エチルビニルキシレン、ビニルナフタ
レンおよびそれらの混合物が挙げられる。中央ブロック
Ｂは、共役ジエン系炭化水素、たとえば１，３−ブタジ
エン、２．３−ジメチルブタジエン、イソプレンおよび
１．３−ペンタジエンわよびそれらの混合物から誘導さ
れたエラストマー状重合体である。各末端ブロックＡお
よびＡ′の分子量は好ましくは約２．０００〜約１０ｏ
．ｏｏｏの範囲であり、一万中央ブロックＢの分子量は
好ましくは約２５．０００〜約１．ｏｏｏ，ｏｏｏの範
囲である。The elastomer component is an elastomer in the general sense of the term, for example A, V, Thbolsk.
“Properties and Structure” by Y.
res of Poly-rrers” (Joh
n%ley & Sons, Inc. , 195
Q) You can cite the definition adopted on pages 71-78,
Elastomer has a Young's modulus of 105 to 10 at room temperature.
dynes/cPI (0-1~102
0 Kq/m). Specific examples of elastomers include A-B-A' type elastomeric blocks,
A-B-A/type elastomeric block copolymer in which the double bond in the polybutadiene portion is hydrogenated, polybutadiene, polyisoprene, copolymer of diene compound and vinyl aromatic compound, nitrile rubber , ethylene-propylene copolymer, ethylene-propylene-gene copolymer (EPDM), thiokol rubber, polysulfide rubber, acrylic acid rubber, polyurethane rubber, graft products of butyl rubber and polyethylene, polyester elastomer, polyamide elastomer, etc. . Particularly desirable are A-B-A/type elastomeric block copolymers. Terminal block A of this block copolymer
and A' is a polymerized vinyl aromatic hydrocarbon block, B is a polymerized conjugated diene block or a conjugated diene block in which most of the double bonds are hydrogenated, and the molecular weight of the B block is the same as that of A and B. It is desirable that the size is larger than the combined molecular size of the A' block. The terminal blocks A and N may be the same or different and are thermoplastic homopolymers or copolymers derived from vinyl aromatic compounds in which the aromatic moiety may be monocyclic or polycyclic. Examples of such vinyl aromatic compounds are:
Styrene, α-methylestyrene, vinyltonoleene,
Mention may be made of vinylxylene, ethylvinylxylene, vinylnaphthalene and mixtures thereof. Central block B is an elastomeric polymer derived from conjugated diene hydrocarbons such as 1,3-butadiene, 2,3-dimethylbutadiene, isoprene and 1,3-pentadiene and mixtures thereof. The molecular weight of each end block A and A' is preferably from about 2.000 to about 100
．． The molecular weight of the central block B is preferably from about 25,000 to about 1.000. The range is ooo, ooo.
前記各種添加剤の例を挙げると、難燃剤の例としては、
トリフェニルホスフェート、トリクレジルホスフェート
、イソプロビルフェノールとフェノールの混合物とオキ
シ塩化リンより得られるホスフェート、ペンゾヒドロキ
ノンあるいはビスフェノールＡのような二官能性フェノ
ールと他のアルコールあるいはフェノール類とオキシ塩
化リンカ）ら得られるホスフェートのようなリン酸エス
テル類；デカブロモビフェニル、ベンタプロモトルエン
、デカブロモビフェニルエーテル、ヘキサブロモベンゼ
ン、ブロム化ポリスチレン等に代表される臭素化化合物
；シアヌル酸誘導体、メラミン誘導体等の含窒素化合物
等を挙げることができる。難燃助剤が使用されてもよく
、その例としては、アンチモン、ほう素、亜鉛あるいは
鉄の化合物などが挙げられる。さらにその池の添加剤と
して立体障害性フェノール、ホスファイト系化合物のご
とき安定剤；サリシレート系化合物、しゆう酸ジアミド
系化合物、立体障害性アミン系化合物で例示される紫外
線吸収剤；ポリエチレンワックス、ポリプロピレンワッ
クス、パラフィンで例示される滑剤等が挙げられる。さ
らには、酸化チタン、硫化亜鉛、酸化亜鉛で例示される
顔料；ガラスＦＩ！．碓、ミルドファイバー、ガラスビ
ーズ、アスベスト、ウオラストナイト、マイカ、タルク
、クレー、炭カル、水酸化マグネシウム，シリカ，チタ
ン酸カリウム繊維、珪藻土、ロックウール、で例示され
る鉱物質充填剤；アルミニウムや亜鉛のフレーク、ある
いは、黄銅、アルミニウム亜鉛等の金属の繊維で代表さ
れる無機充填剤；炭素繊維に代表される有機充填剤を挙
げることができる。To give examples of the various additives mentioned above, examples of flame retardants include:
triphenyl phosphate, tricresyl phosphate, phosphates obtained from isopropylphenol and phenol mixtures and phosphorus oxychloride, difunctional phenols such as penzohydroquinone or bisphenol A and other alcohols or phenols and oxychloride linkers) Phosphate esters such as phosphates obtained from Examples include nitrogen compounds. Flame retardant aids may be used, examples include antimony, boron, zinc or iron compounds. Furthermore, as additives, stabilizers such as sterically hindered phenols and phosphite compounds; ultraviolet absorbers such as salicylate compounds, oxalic acid diamide compounds, and sterically hindered amine compounds; polyethylene wax, polypropylene Examples include lubricants such as wax and paraffin. Furthermore, pigments such as titanium oxide, zinc sulfide, and zinc oxide; Glass FI! ．． Mineral fillers exemplified by milled fibers, glass beads, asbestos, wollastonite, mica, talc, clay, charcoal, magnesium hydroxide, silica, potassium titanate fibers, diatomaceous earth, rock wool; aluminum and Inorganic fillers typified by zinc flakes or fibers of metals such as brass and aluminum zinc; and organic fillers typified by carbon fibers.
以上に述べたごとく本発明の樹指組戊物は、相溶性が改
善され、機械的強度、耐熱性Ｉこ優れかつ、耐溶剤性が
非常に優れており、更にガラス繊維で強化することによ
り機減的強度、耐男性が驚くほど向上しかつ、耐溶剤性
が非常に優れているため、機械構造材料、電気、電子部
品などの用途に有用である。As described above, the resin composite of the present invention has improved compatibility, excellent mechanical strength, excellent heat resistance, and extremely excellent solvent resistance. It is useful for applications such as mechanical structural materials, electrical and electronic parts, because it has surprisingly improved mechanical strength and corrosion resistance, and extremely excellent solvent resistance.
以下参考例、実施例および比較例により本発明の樹脂組
成物を説明する。The resin composition of the present invention will be explained below with reference to Reference Examples, Examples, and Comparative Examples.
参考例 １
２５℃でクロロホルム中で測定された極限粘度がＯ．・
４ ７ （ｄ Ｉｔ／９”） の２．６−ジメチルフ
ェノール／２，３．６−｝リメチルフェノール共重合体
（２． ３． ６−｝リメチルフェノールの占める
割合は５モル％）３Ｋｇに無水マレイン酸 ９０ｇを添
加しヘンシェルミキサーにより混合した後、二軸押出桟
で３００〜３２０℃の温度で溶融混練しベレット化した
。Reference Example 1 The intrinsic viscosity measured in chloroform at 25°C is O.・
4 7 (d It/9”) of 2.6-dimethylphenol/2,3.6-}limethylphenol copolymer (the proportion of 2.3.6-}limethylphenol is 5 mol%) 3Kg 90 g of maleic anhydride was added thereto and mixed using a Henschel mixer, and then melt-kneaded using a twin-screw extrusion bar at a temperature of 300 to 320°C to form pellets.
得られたベレット ２ｇをクロロホルム ５０一に溶解
した後、この溶岐にアセトン ５００−を加えてポリマ
ーを沈殿せしめた。得られたポリマーをＰ別、乾燥した
（減圧下、８０℃１０時間）。得られた試料の赤外分光
分析を行ない、ポリフェニレンエーテルと無水マレイン
酸とから荊もって作成しておいた検量線を用いて、ポリ
フェニレンエーテルに結合している無水マレイン酸のｆ
ｆｉ量％を算出し、無水マレイン酸の結合量とした。無
水マレイン酸の結合量は１．１重１ｌｉ％であった。After dissolving 2 g of the obtained pellet in 50% chloroform, 500% acetone was added to the solution to precipitate the polymer. The obtained polymer was separated from P and dried (under reduced pressure at 80° C. for 10 hours). The obtained sample was analyzed by infrared spectroscopy, and using a calibration curve prepared from polyphenylene ether and maleic anhydride, f of maleic anhydride bonded to polyphenylene ether was determined.
The amount of fi (%) was calculated and taken as the amount of maleic anhydride bound. The amount of maleic anhydride bound was 1.1% by weight and 1li%.
参考例 ２
参考例１のポリフェニレンエーテル ３ Ｋｐに無水マ
レイン酸 ９０ｇと１５ｇのジクミルバ−オキサイドを
加えたものをへ冫シェノレミキサーで混合した後、二軸
押出機で３００〜３２０℃で溶融混棟を行ないペレット
化した。得ラレたベレットを参考例１と同様に処理、分
析したところ、無水マレイン酸の結合量は１．９重量％
であった。Reference Example 2 The polyphenylene ether 3 Kp of Reference Example 1 was mixed with 90 g of maleic anhydride and 15 g of dicumyl peroxide in a hexagonal mixer, and then melted and blended at 300 to 320°C in a twin-screw extruder. It was made into pellets. When the obtained lare pellet was treated and analyzed in the same manner as in Reference Example 1, the amount of bound maleic anhydride was 1.9% by weight.
Met.
参考例 ３
参考例１のボリフェニレンエーテルをポリ（２．６−ジ
メチル−１．４−フェニレン）エーテルに代えて参考例
１を繰り返した。無水マレイン酸の結合母は０．９１ｉ
１１％であった。Reference Example 3 Reference Example 1 was repeated except that polyphenylene ether in Reference Example 1 was replaced with poly(2,6-dimethyl-1,4-phenylene) ether. The bonding mother of maleic anhydride is 0.91i
It was 11%.
参考列 ４
ポリフェニレンスルフィドの粉末（■トープレン製，ト
ープレンＴ−４、溶融粘度 ２８００ｐｏｉｓｅ （
３ ０ ０℃）） １００重員部と、５９６ＨＣｇ
水溶液 ３００ｉｉ量部およびアセトン ５０重量部を
還流下で１０時間攪拌混合した。Reference row 4 Polyphenylene sulfide powder (made by Toprene, Toprene T-4, melt viscosity 2800 poise (
300℃)) 100 parts by weight and 596HCg
300 parts by weight of the aqueous solution and 50 parts by weight of acetone were stirred and mixed under reflux for 10 hours.
得られたボリフェニレンスルフィドの粉末を水／アセト
ン混合溶媒で充分洗浄した後、８０℃で２４時間真空乾
燥を行かい、ＳＨ化ポリフェニレンスルフィド粉末を得
た。The obtained polyphenylene sulfide powder was thoroughly washed with a water/acetone mixed solvent and then vacuum dried at 80° C. for 24 hours to obtain an SH-modified polyphenylene sulfide powder.
得られた粉末を苛性ソーダで滴定し、樹＠１Ｋｆ当たり
１５ミリグラム当瓜のＳＨ末端基を確認した。The obtained powder was titrated with caustic soda to confirm the SH terminal group of 15 mg per 1 Kf of the melon.
実施例 １
参考例１で得られた無水マレイン酸変性ポリフェニレン
エーテルのベレット ４０ｉ１Ｈｌｆ［参考例４で得ら
れたＳＨ化ポリフェニレンスルフィド ６０重量部を混
合後、２軸押出機により２９０〜３２０℃で溶融混練を
行ないペレット化した。得られたべレフトを射出成形し
， Ｌ／８インチ厚の引張り試験用ダンベル片と、アイ
ゾット衝撃試験片及び１／４インチ厚の熱変形温度測定
用試験片を得た。これらの試験片を用いて引張強度、ア
イゾット衝撃強度（ノッチ無し）及び１８．ｉ荷重で熱
変形温度を測定した。Example 1 A pellet of maleic anhydride-modified polyphenylene ether obtained in Reference Example 1 40i1Hlf [After mixing 60 parts by weight of SH-modified polyphenylene sulfide obtained in Reference Example 4, melt kneading was performed at 290 to 320°C using a twin-screw extruder. It was made into pellets. The obtained beam left was injection molded to obtain L/8 inch thick dumbbell pieces for tensile testing, Izod impact test pieces, and 1/4 inch thick test pieces for heat distortion temperature measurement. Using these test pieces, tensile strength, Izod impact strength (without notch) and 18. The heat distortion temperature was measured under i load.
また得られたベレット ４９をクロロホルムにて１６時
間ソックスレー・抽出を行なった。抽出残査を８０℃で
２４時間真空乾燥し柚出残査の割合を求めた。Further, the obtained pellet 49 was subjected to Soxhlet extraction with chloroform for 16 hours. The extraction residue was vacuum dried at 80° C. for 24 hours, and the proportion of the yuzu residue was determined.
以上の結果を表１に示した。The above results are shown in Table 1.
比較例 ｌ
参考例１で得られた無水マレイン酸変性ポリフェニレン
エーテルのペレット ４ｏｍｍ部とボリフェニレンスル
フィドのべレットＣ（ｍト−プレン製、トープレンＴ−
４、溶融粘度 ２８０ （Ｎ）Ｏｉｇｅ （３ ０ ０
℃）〕 ６０重量部を混合し、実施例１と同様の操作を
行なった。Comparative Example l 4 om part of pellets of maleic anhydride-modified polyphenylene ether obtained in Reference Example 1 and polyphenylene sulfide pellet C (manufactured by Toprene, Toprene T-
4. Melt viscosity 280 (N) Oige (3 0 0
℃)] 60 parts by weight were mixed and the same operation as in Example 1 was performed.
結果を表１に示した。The results are shown in Table 1.
実施例 ２〜４
実施例１の変性ポリフェニレンエーテルト３１｛化ボリ
フエニレンスルフィドを使用し、表１に示す組成で実施
例１と同様の操作を行った。Examples 2 to 4 The same operations as in Example 1 were carried out using the modified polyphenylene ether 31{polyphenylene sulfide of Example 1 and the composition shown in Table 1.
結果を表１に示した。The results are shown in Table 1.
比較例 ２〜４ 結果は表２１ζ示した。Comparative examples 2 to 4 The results are shown in Table 21ζ.
実施例１の変性ボリフェニレンエーテルとボリフェニレ
ンスルフィドを使用し表１に示す組成で実施例１と同様
の操作を行なった。The same operation as in Example 1 was carried out using the modified polyphenylene ether and polyphenylene sulfide of Example 1 and the composition shown in Table 1.
結果を表１に示した。The results are shown in Table 1.
実施例 ５
参考例２で得られた無水マレイン酸変性ポリフェニレン
エーテルのべレフト ４０重ｆｆｌ部と参考例４で得ら
れたＳＨ化ポリフェニレンスルフィド ６０重量部を混
合後、実施例１と同様・の操作を行なった。Example 5 After mixing 40 parts by weight of beleft of the maleic anhydride-modified polyphenylene ether obtained in Reference Example 2 and 60 parts by weight of the SH-modified polyphenylene sulfide obtained in Reference Example 4, the same operation as in Example 1 was carried out. I did it.
結果を表２に示した。The results are shown in Table 2.
実施例 ６
参考例３で得られた無水マレイン酸変性ボリフェニレン
エーテル ５０重量部と参考例４で得ラれたＳＨ化ポリ
フェニレンスルフイト５０重量部を混合後実施例１と同
様の操作を行なった。Example 6 After mixing 50 parts by weight of maleic anhydride-modified polyphenylene ether obtained in Reference Example 3 and 50 parts by weight of SH-modified polyphenylene sulfite obtained in Reference Example 4, the same operation as in Example 1 was carried out. Ta.
比較例 ５
参考例２で得られた無水マレイン酸変性ポリフェニレン
エーテルのベレット ４０１ｉｆｆｉ部トポリフェニレ
ンスルフィドのべレット（ｆｍトープレン製、トープレ
ンＴ−４Ｐ１溶融粘度 ２８ ０ ０ｐｏｉｓｅ （３
０ ０℃）〕 ６０重量部を混合後、実施例１と同
様の操作を行なった。Comparative Example 5 A pellet of maleic anhydride-modified polyphenylene ether obtained in Reference Example 2. A pellet of polyphenylene sulfide (manufactured by fm Toprene, Toprene T-4P1, melt viscosity 280 0 poise (3
0 0°C)] After mixing 60 parts by weight, the same operation as in Example 1 was performed.
結果を表２に示した。The results are shown in Table 2.
比較例 ６
参考例３で得られた無水マレイン酸変性ポリフエニレン
エーテル ５０！ｉｆｉ１部トボリフェニレンスルフィ
ド（（４！ｌ−プレン製、トープレンＴ−４Ｐ） ５
０重量部を混合後実施例１と同様の操作を行なった。Comparative Example 6 Maleic anhydride-modified polyphenylene ether obtained in Reference Example 3 50! ifi 1 part Topolyphenylene sulfide ((4! L-Prene, Toprene T-4P) 5
After mixing 0 parts by weight, the same operation as in Example 1 was performed.
結果は表２に示した。The results are shown in Table 2.
実施例 ７〜１０
実施例１の無水マレイン酸変性ボリフェニレンエーテル
，ｌ：、ＳＨ化ポリフェニレンスルフィドとガラス４維
（旭ファイバーグラス（ｍＨ ＣＳＱ３ＭＡ４０４）
を表３に示した割合で混合した後、実施例１と同様の操
作を行なった。Examples 7 to 10 Maleic anhydride-modified polyphenylene ether of Example 1, 1: SH-modified polyphenylene sulfide and glass 4 fiber (Asahi fiberglass (mH CSQ3MA404)
After mixing in the proportions shown in Table 3, the same operation as in Example 1 was performed.
結果は表３に示した。The results are shown in Table 3.
比較列 ７〜１０
実施例１の無水マレイン酸変性ボリフェニレンエーテル
、ポリフエニレンスルフィドとガラス＃ｌＩ．ｍ ＜旭
ファイバーグ凭ス■製 ＣＳＱ３ＭＡ４０４）を表３に
示した割合で混合した後、実施例７〜１０と同様の操作
を行なった。Comparison rows 7-10 Maleic anhydride-modified polyphenylene ether of Example 1, polyphenylene sulfide and glass #lI. After mixing CSQ3MA404 (manufactured by Asahi Fiberglass Co., Ltd.) in the proportions shown in Table 3, the same operations as in Examples 7 to 10 were performed.
結果は表３に示した。The results are shown in Table 3.
表 ２table 2
Claims (1)
ン性二重結合と、（ｂ）カルボキシル基または酸無水物
基を有する有機化合物から選ばれた変性剤でラジカル開
始剤の存在下又は非存在下に変性して得られる変性ポリ
フェニレンエーテルと （Ｂ）ＳＨ末端基の濃度が、樹脂１Ｋｇにつき１０ミリ
グラム当量以上であるポリフェニレンスルフィド からなる新規な耐熱耐溶剤性樹脂組成物[Scope of Claims] (A) Polyphenylene ether is used as a radical initiator with a modifier selected from organic compounds having (a) an ethylenic double bond and (b) a carboxyl group or an acid anhydride group in the molecule. A novel heat- and solvent-resistant resin composition comprising a modified polyphenylene ether obtained by modification in the presence or absence of polyphenylene ether and (B) a polyphenylene sulfide in which the concentration of SH terminal groups is 10 milligram equivalents or more per 1 kg of resin.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14944989A JP2805847B2 (en) | 1989-06-14 | 1989-06-14 | New heat and solvent resistant resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14944989A JP2805847B2 (en) | 1989-06-14 | 1989-06-14 | New heat and solvent resistant resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0317153A true JPH0317153A (en) | 1991-01-25 |
| JP2805847B2 JP2805847B2 (en) | 1998-09-30 |
Family
ID=15475365
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14944989A Expired - Fee Related JP2805847B2 (en) | 1989-06-14 | 1989-06-14 | New heat and solvent resistant resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2805847B2 (en) |
-
1989
- 1989-06-14 JP JP14944989A patent/JP2805847B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2805847B2 (en) | 1998-09-30 |
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