JPH04114052A - Thermoplastic resin composition - Google Patents
Thermoplastic resin compositionInfo
- Publication number
- JPH04114052A JPH04114052A JP23253990A JP23253990A JPH04114052A JP H04114052 A JPH04114052 A JP H04114052A JP 23253990 A JP23253990 A JP 23253990A JP 23253990 A JP23253990 A JP 23253990A JP H04114052 A JPH04114052 A JP H04114052A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- group
- formula
- unsaturated
- thermoplastic resin
- 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.)
- Pending
Links
- 229920005992 thermoplastic resin Polymers 0.000 title claims abstract description 12
- 239000011342 resin composition Substances 0.000 title claims abstract description 8
- 229920001577 copolymer Polymers 0.000 claims abstract description 32
- 229920000098 polyolefin Polymers 0.000 claims abstract description 19
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 238000004898 kneading Methods 0.000 claims abstract description 13
- 229920006122 polyamide resin Polymers 0.000 claims abstract description 13
- 125000000524 functional group Chemical group 0.000 claims abstract description 10
- 150000001451 organic peroxides Chemical class 0.000 claims abstract description 10
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 10
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims abstract description 4
- 239000002184 metal Substances 0.000 claims abstract description 4
- -1 unsaturated dicarboxylic acid imide Chemical class 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000004018 acid anhydride group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 6
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 239000004593 Epoxy Substances 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 238000005452 bending Methods 0.000 abstract 1
- 150000007942 carboxylates Chemical class 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000004952 Polyamide Substances 0.000 description 13
- 229920002647 polyamide Polymers 0.000 description 13
- 238000000034 method Methods 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 10
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920001778 nylon Polymers 0.000 description 4
- 229920002292 Nylon 6 Polymers 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-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
- 229920000299 Nylon 12 Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000004984 aromatic diamines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- SXTILEHINBCKSS-UHFFFAOYSA-N 1-chloro-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(Cl)C(=O)C=C1C1=CC=CC=C1 SXTILEHINBCKSS-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- HHVCCCZZVQMAMT-UHFFFAOYSA-N 1-hydroxy-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(O)C(=O)C=C1C1=CC=CC=C1 HHVCCCZZVQMAMT-UHFFFAOYSA-N 0.000 description 1
- QCOLXFOZKYRROA-UHFFFAOYSA-N 1-methoxy-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(OC)C(=O)C=C1C1=CC=CC=C1 QCOLXFOZKYRROA-UHFFFAOYSA-N 0.000 description 1
- QSWFISOPXPJUCT-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidine-2,5-dione Chemical compound CN1C(=O)CC(=C)C1=O QSWFISOPXPJUCT-UHFFFAOYSA-N 0.000 description 1
- IYBPIDAYDPNCTP-UHFFFAOYSA-N 1-methyl-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(C)C(=O)C=C1C1=CC=CC=C1 IYBPIDAYDPNCTP-UHFFFAOYSA-N 0.000 description 1
- PSKLSRMDQQEEGQ-UHFFFAOYSA-N 1-nitro-3-phenylpyrrole-2,5-dione Chemical compound O=C1N([N+](=O)[O-])C(=O)C=C1C1=CC=CC=C1 PSKLSRMDQQEEGQ-UHFFFAOYSA-N 0.000 description 1
- NQDOCLXQTQYUDH-UHFFFAOYSA-N 1-propan-2-ylpyrrole-2,5-dione Chemical compound CC(C)N1C(=O)C=CC1=O NQDOCLXQTQYUDH-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
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- CEBRPXLXYCFYGU-UHFFFAOYSA-N 3-methylbut-1-enylbenzene Chemical compound CC(C)C=CC1=CC=CC=C1 CEBRPXLXYCFYGU-UHFFFAOYSA-N 0.000 description 1
- JLLCBHHFPWVBQP-UHFFFAOYSA-N 3-methylidene-1-phenylpyrrolidine-2,5-dione Chemical compound O=C1C(=C)CC(=O)N1C1=CC=CC=C1 JLLCBHHFPWVBQP-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000004953 Aliphatic polyamide Substances 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000572 Nylon 6/12 Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- SIIVGPQREKVCOP-UHFFFAOYSA-N but-1-en-1-ol Chemical compound CCC=CO SIIVGPQREKVCOP-UHFFFAOYSA-N 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 230000000739 chaotic effect Effects 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- ZMUCVNSKULGPQG-UHFFFAOYSA-N dodecanedioic acid;hexane-1,6-diamine Chemical compound NCCCCCCN.OC(=O)CCCCCCCCCCC(O)=O ZMUCVNSKULGPQG-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000088 plastic resin Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical compound CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明は、耐熱性、耐薬品性及び成形加工性二こ優れた
熱可塑性樹脂Sこ関する。DETAILED DESCRIPTION OF THE INVENTION <Industrial Application Field> The present invention relates to a thermoplastic resin S having two excellent heat resistance, chemical resistance, and moldability.
更に詳しくは、不飽和ジカルボン酸イミド誘導体基を有
する芳香族ビニル系重合体(以下、イミド化共重合体と
記す。)と特定の有機過酸化物またはビヘンジル誘導体
を溶融混練して得られる低粘度熱可塑性樹脂(以下、低
粘度イミド化共重合体と記す。)とポリアミド樹脂及び
特定の官能基で変性されたポリオレフィンとを溶融混練
してなる、成形加工性に優れた熱可塑性樹脂組成物に関
する。More specifically, a low viscosity polymer obtained by melt-kneading an aromatic vinyl polymer having an unsaturated dicarboxylic acid imide derivative group (hereinafter referred to as an imidized copolymer) and a specific organic peroxide or bihenzyl derivative. A thermoplastic resin composition with excellent moldability, which is obtained by melt-kneading a thermoplastic resin (hereinafter referred to as a low-viscosity imidized copolymer), a polyamide resin, and a polyolefin modified with a specific functional group. .
〈従来の技術及び問題点〉
ポリアミド樹脂は、優れた機械的性質、耐薬品性及び成
形加工性を有していることから、広く一般に使用されて
いる。しかしながら、ポリアミド樹脂は吸湿性が大きく
、吸湿による寸法変化、機械的強度の低下が実用上の問
題となっている。<Prior Art and Problems> Polyamide resins are widely used because they have excellent mechanical properties, chemical resistance, and moldability. However, polyamide resins are highly hygroscopic, and dimensional changes and reductions in mechanical strength due to moisture absorption pose practical problems.
これらの問題を解決するために、特開昭57−5771
9号公報、特開昭58−71952号公報、特開昭60
−86162号公報、特開昭60195157号公報、
特開昭64−79243号公報及び特開平1−2104
44号公報には、ポリアミドに、吸湿性の小さい芳香族
ビニル系の重合体を混合する方法が記載されている。こ
の場合、相溶性を付加するために芳香族ビニル化合物に
不飽和ジカルボン酸無水物や不飽和ジカルボン酸イミド
誘導体を共重合する方法がとられている。In order to solve these problems, Japanese Patent Application Laid-Open No. 57-5771
9, JP-A-58-71952, JP-A-60
-86162 publication, JP 60195157 publication,
JP-A-64-79243 and JP-A-1-2104
No. 44 describes a method of mixing an aromatic vinyl polymer with low hygroscopicity into polyamide. In this case, in order to add compatibility, a method is used in which an unsaturated dicarboxylic acid anhydride or an unsaturated dicarboxylic acid imide derivative is copolymerized with the aromatic vinyl compound.
しかしながら、これらの方法では、何れも、得られる樹
脂組成物の靭性が低く、実用上問題があった。また、特
開昭62−59647号公報及び特開昭63−1050
51号公報には、イミド化共重合体とポリアミドの混合
物に特定のゴム状重合体を添加して衝撃性を改良する方
法が記載されている。しかしながら、これらの方法でも
、それぞれの成分の相溶性が充分でなく、得られる樹脂
塑性物の機械的性質、特に引っ張り伸度が低くかったり
、得られる樹脂塑性物の成形加工性が悪い等、実用上満
足できるものではなかった。However, in all of these methods, the resulting resin composition has low toughness, which poses a practical problem. Also, JP-A-62-59647 and JP-A-63-1050
No. 51 describes a method of improving impact properties by adding a specific rubbery polymer to a mixture of an imidized copolymer and a polyamide. However, even with these methods, the compatibility of the respective components is not sufficient, and the mechanical properties of the obtained plastic resin, especially the tensile elongation, are low, and the moldability of the obtained resin plastic is poor, etc. It was not practically satisfactory.
〈問題の解決方法〉
本発明は、イミド化共重合体と特定の有機過酸化物また
はビベンジル誘導体を溶融混練して得られる低粘度イミ
ド化共重合体とポリアミド及び特定の官能基で変性され
たポリオレフィンを溶融混練することにより、引っ張り
伸びの大きい樹脂組成物が得られることを見出した。す
なわち、本発明は、
A成分:芳香族ビニル単量体30〜70重量%、不飽和
ジカルボン酸イミド誘導体0〜60重量%、不飽和ジカ
ルボン酸無水物単量体1〜10重量%、及びそれら以外
の不飽和単量体0〜40重量%とからなるイミド化共重
合体100重量部と、下記(1)式または(2)式で表
される有機過酸化物または下記(3)式で表されるビベ
ンジル誘導体0、1〜10重量部を溶融混練して得られ
る低粘度熱可塑性樹脂10〜80重量%と、
R’−0−0−R” (1)R’−
0−0−X−0−0−R” (2)(式中、R’
、R”、R”及びR4は各々水素原子、またはハロゲ
ン原子、または炭素数1〜5の直鎖または分岐アルキル
基、またはシクロアルキル基またはアリール基、または
置換アリール基を表し、Xは炭素数1〜10の飽和、又
は、不飽和の直鎖、又は、分岐の2価の原子団、又は芳
香環を含む炭素数6〜15の2価の原子団を表す。)B
成分:ポリアミド樹脂20〜90重量%及び、C成分:
カルボキシル基、酸無水物基、エポキシ基、カルボン酸
金属塩基、ヒドロキシル基及びアミノ基から選ばれる少
なくとも1種の官能基で変性されたポリオレフィン1〜
30重量%を溶融混練してなる熱可塑性樹脂組成物に関
する。<Method for solving the problem> The present invention provides a low-viscosity imidized copolymer obtained by melt-kneading an imidized copolymer and a specific organic peroxide or bibenzyl derivative, a polyamide, and a polyamide modified with a specific functional group. It has been found that a resin composition with high tensile elongation can be obtained by melt-kneading polyolefin. That is, the present invention provides the following components: A component: 30 to 70% by weight of aromatic vinyl monomer, 0 to 60% by weight of unsaturated dicarboxylic acid imide derivative, 1 to 10% by weight of unsaturated dicarboxylic acid anhydride monomer, and 100 parts by weight of an imidized copolymer consisting of 0 to 40% by weight of unsaturated monomers other than 0 to 40% by weight, and an organic peroxide represented by the following formula (1) or (2) or the following formula (3). 10 to 80% by weight of a low-viscosity thermoplastic resin obtained by melt-kneading 0.1 to 10 parts by weight of the bibenzyl derivative represented by R'-0-0-R" (1) R'-
0-0-X-0-0-R" (2) (wherein, R'
, R", R" and R4 each represent a hydrogen atom, a halogen atom, a straight chain or branched alkyl group having 1 to 5 carbon atoms, a cycloalkyl group, an aryl group, or a substituted aryl group, and X is a carbon number It represents a saturated or unsaturated linear or branched divalent atomic group of 1 to 10, or a divalent atomic group of 6 to 15 carbon atoms containing an aromatic ring. ) B
Ingredients: 20 to 90% by weight of polyamide resin and component C:
Polyolefin modified with at least one functional group selected from carboxyl group, acid anhydride group, epoxy group, carboxylic acid metal base, hydroxyl group and amino group 1-
It relates to a thermoplastic resin composition formed by melt-kneading 30% by weight.
本発明A成分に用いるイミド化共重合体の製造方法とし
て一例を挙げると芳香族ビニル単量体、不飽和ジカルボ
ン酸イミド誘導体、不飽和ジカルボン酸無水物単量体及
び、必要ならばそれらと共重合可能な他の不飽和ビニル
誘導体を公知の方法で共重合させて得ることができる。One example of the method for producing the imidized copolymer used as component A of the present invention is to use an aromatic vinyl monomer, an unsaturated dicarboxylic acid imide derivative, an unsaturated dicarboxylic acid anhydride monomer, and, if necessary, a copolymer thereof. It can be obtained by copolymerizing other polymerizable unsaturated vinyl derivatives by a known method.
芳香族ビニル単量体としてはスチレン、メチルスチレン
、ジメチルスチレン、モノクロルスチレン、ジクロルス
チレン、モノフロムスチレン、シフロムスチレン、イソ
プロピルスチレン、L−メチルスチレン、エチルスチレ
ン、ビニルナフタレン等があり、スチレンが好ましい。Aromatic vinyl monomers include styrene, methylstyrene, dimethylstyrene, monochlorostyrene, dichlorostyrene, monofuromstyrene, sifuromestyrene, isopropylstyrene, L-methylstyrene, ethylstyrene, vinylnaphthalene, etc. preferable.
これら芳香族ビニル単量体は、単独または2種以上併用
して用い、それらの使用量は、30〜70重量%、好ま
しくは40〜60重量%である。These aromatic vinyl monomers are used alone or in combination of two or more, and the amount used is 30 to 70% by weight, preferably 40 to 60% by weight.
該使用量が30重量%未満では寸法安定性が損なわれ、
70重量%を越えると耐熱性が低下する。If the amount used is less than 30% by weight, dimensional stability will be impaired,
If it exceeds 70% by weight, heat resistance will decrease.
不飽和ジカルボン酸イミド誘導体としては、マレイミド
、N−メチルマレイミド、N−エチルマレイミド、N−
ブチルマレイミド、N−シクロへキシルマレイミド、N
−フェニルマレイミド、Nメチルフェニルマレイミド、
N−ヒドロキシフェニルマレイミド、N−メトキシフェ
ニルマレイミド、N−クロルフェニルマレイミド、N−
ニトロフェニルマレイミド、N−ベンジルマレイミド、
N−イソプロピルマレイミド、N−メチルイタコン酸イ
ミド、N−フェニルイタコン酸イミド等が挙げられ、こ
れらの中でN−フェニルマレイミドが好ましく用いられ
る。Examples of unsaturated dicarboxylic acid imide derivatives include maleimide, N-methylmaleimide, N-ethylmaleimide, N-
Butylmaleimide, N-cyclohexylmaleimide, N
-phenylmaleimide, N-methylphenylmaleimide,
N-hydroxyphenylmaleimide, N-methoxyphenylmaleimide, N-chlorophenylmaleimide, N-
Nitrophenylmaleimide, N-benzylmaleimide,
Examples include N-isopropylmaleimide, N-methylitaconimide, N-phenylitaconimide, and among these, N-phenylmaleimide is preferably used.
これらの不飽和ジカルボン酸イミド誘導体は、単独また
は2種以上で使用され、その使用量は、30〜60重量
%、好ましくは40〜55重四%である。該使用量が3
0重量%未満では耐熱性向上に顕著な効果が発揮できず
、60重量%を越えると樹脂が詭(なる。These unsaturated dicarboxylic acid imide derivatives may be used alone or in combination of two or more, and the amount used is 30 to 60% by weight, preferably 40 to 55% by weight. The usage amount is 3
If it is less than 0% by weight, no remarkable effect on improving heat resistance can be exhibited, and if it exceeds 60% by weight, the resin will deteriorate.
不飽和ジカルボン酸無水物としては、マレイン酸、イタ
コン酸、シトラコン酸等の無水物が挙げられ、これらは
単独または2種以上併用して用いられるが、無水マレイ
ン酸が特に好ましい。これら不飽和ジカルボン酸無水物
の使用量は1〜10重量%、好ましくは2〜6重景%で
あり、該使用量が1重量%未満ではポリアミドとの相溶
性が劣り、10重量%を越えると熱安定性が低下する。Examples of the unsaturated dicarboxylic anhydride include anhydrides such as maleic acid, itaconic acid, and citraconic acid, which may be used alone or in combination of two or more, with maleic anhydride being particularly preferred. The amount of these unsaturated dicarboxylic acid anhydrides used is 1 to 10% by weight, preferably 2 to 6% by weight; if the amount is less than 1% by weight, the compatibility with polyamide is poor, and if it exceeds 10% by weight. and thermal stability decreases.
それらと共重合可能な他の不飽和ビニル誘導体としては
、アクリロニトリル、メタクリロニトリル等のシアン化
ビニル単量体、アクリル酸、メタクリル酸等の不飽和カ
ルボン酸、メタクリル酸エステル等の不飽和カルボン酸
エステル類等が挙げられる。Other unsaturated vinyl derivatives that can be copolymerized with them include vinyl cyanide monomers such as acrylonitrile and methacrylonitrile, unsaturated carboxylic acids such as acrylic acid and methacrylic acid, and unsaturated carboxylic acids such as methacrylic acid esters. Examples include esters.
これらの使用量は、0〜40重量%、好ましくは、0〜
30重量%であり、該使用量が40重量%を越えると耐
熱性及び熱安定性が低下する。The amount of these used is 0 to 40% by weight, preferably 0 to 40% by weight.
30% by weight, and if the amount used exceeds 40% by weight, heat resistance and thermal stability will decrease.
これらの単量体成分を共重合させて得られる重合物と同
し組成を持つものならば製造方法は問わず、芳香族ビニ
ル単量体、不飽和ジカルボン酸無水物、及び必要とあら
ばそれらと共重合可能な他の不飽和ビニル誘導体を共重
合させた後、アンモニアまたは第一級アミンを用いて酸
無水物基をイミド化して得られる重合物も好ましく使用
できる。Regardless of the manufacturing method, as long as it has the same composition as the polymer obtained by copolymerizing these monomer components, aromatic vinyl monomers, unsaturated dicarboxylic acid anhydrides, and if necessary, A polymer obtained by copolymerizing other unsaturated vinyl derivatives that can be copolymerized with the polymer, and then imidizing the acid anhydride group using ammonia or a primary amine can also be preferably used.
A成分に使用する有機過酸化物としては下記(1)式ま
たは(2)式で表されるものが使用できる。As the organic peroxide used for component A, those represented by the following formula (1) or (2) can be used.
R’−0−0−R” (1)R’−C
)−0−X−0−0−R2(2)(式中、R’及びRz
は各々水素原子、またはハロゲン原子(例えば塩素、臭
素など)、または炭素数1〜5の直鎖または分岐アルキ
ル基(例えば、メチル、エチル、ブチル、プロピル基な
ど)またはシクロアルキル基(例えばシクロヘキシル基
など)、またはアリール基(例えばフェニル、ナフチル
基など)、または置換アリール基(例えばトルイル、キ
シリル基など)を表し、Xは炭素数1〜10の飽和また
は不飽和の直鎖または分岐の2価の原子団、または芳香
環を含む炭素数6〜15の2価の原子団を表す。)
これらの過酸化物の中でL−ブチルハイドロパーオキサ
イド、キュメンハイドロパーオキサイド、2.5−ジメ
チル−2,5−ジ(t−ブチルパーオキシ)ヘキサン、
2.5−ジメチル−2,5−ジ(t−ブチルパーオキシ
)ヘキシン−3及び2.5−ジメチルヘキサン2.5−
シバイドロバ−オキサイド等が好ましく使用できる。R'-0-0-R" (1) R'-C
)-0-X-0-0-R2(2) (wherein, R' and Rz
each represents a hydrogen atom, or a halogen atom (e.g., chlorine, bromine, etc.), or a linear or branched alkyl group having 1 to 5 carbon atoms (e.g., methyl, ethyl, butyl, propyl group, etc.) or a cycloalkyl group (e.g., cyclohexyl group). ), or an aryl group (e.g. phenyl, naphthyl group, etc.), or a substituted aryl group (e.g. tolyl, xylyl group, etc.), and X represents a saturated or unsaturated linear or branched divalent group having 1 to 10 carbon atoms. or a divalent atomic group having 6 to 15 carbon atoms and containing an aromatic ring. ) Among these peroxides, L-butyl hydroperoxide, cumene hydroperoxide, 2,5-dimethyl-2,5-di(t-butylperoxy)hexane,
2,5-dimethyl-2,5-di(t-butylperoxy)hexyne-3 and 2,5-dimethylhexane 2,5-
Oxide robber oxide and the like can be preferably used.
ビベンジル誘導体としては下記(3)式で表されるもの
が使用できるが、2.3−ジメチル−2,3−ジフェニ
ルブタン、2.2.3.3−テトラフェニルブタンが特
に好ましい。As the bibenzyl derivative, those represented by the following formula (3) can be used, but 2,3-dimethyl-2,3-diphenylbutane and 2.2.3.3-tetraphenylbutane are particularly preferred.
R’ R3
(式中、R1、Rz 、R3及びR4は各々水素原子、
またはハロゲン原子(例えば塩素、臭素など)、または
炭素数1〜5の直鎖または分岐アルキル基(例えばメチ
ル、エチル、プロピル、ブチル基など)、またはシクロ
アルキル基(例えばシクロヘキシル基など)、またはア
リール基(例えばフェニル、ナフチル基など)、または
置換アリール基を表す(例えばトルイル、キシリル基な
ど)。)
これら有機過酸化物、ビベンジル誘導体は単独または2
種以上併用して用いられ、その使用量はイミド化共重合
体100重量部に対して0.1〜10重量部、好ましく
は0.2〜5重量部であり、0.1重量部未満では粘度
の低下の効果が少なく、10重量部を越えると樹脂が脆
くなる。R' R3 (wherein R1, Rz, R3 and R4 are each a hydrogen atom,
or a halogen atom (e.g., chlorine, bromine, etc.), or a linear or branched alkyl group having 1 to 5 carbon atoms (e.g., methyl, ethyl, propyl, butyl group, etc.), or a cycloalkyl group (e.g., cyclohexyl group, etc.), or an aryl group. represents a group (eg, phenyl, naphthyl, etc.) or a substituted aryl group (eg, tolyl, xylyl, etc.). ) These organic peroxides and bibenzyl derivatives may be used alone or in combination.
The amount used is 0.1 to 10 parts by weight, preferably 0.2 to 5 parts by weight, and less than 0.1 parts by weight, based on 100 parts by weight of the imidized copolymer. The effect of reducing viscosity is small, and if it exceeds 10 parts by weight, the resin becomes brittle.
また、本発明のB成分のポリアミド樹脂は特に制限はな
く、ジカルボン酸とジアミンから得られるポリアミド、
アミノカルボン酸あるし)番よラクタム類から得られる
ポリアミドを用(すること力くできる。具体例を挙げる
とナイロン6、ナイロン6・6、ナイロン6・9、ナイ
ロン4・6、ナイロン6・10、ナイロン6・12、ナ
イロン11、ナイロン12等の脂肪族ポリアミドあるし
1番まテレフタル酸、イソフタル酸等の芳香族ジカルボ
ン酸とメタキシリレンジアミン等の芳香族ジアミンまた
は脂肪族ジアミンから得られる芳香族、半芳香M!ポリ
アミド、メタキシリレンジアミン等の芳香1契ジアミン
と脂肪族ジカルボン酸から得られるポIJアミドおよび
それらの共重合体や混合物力((吏用できる。In addition, the polyamide resin of component B of the present invention is not particularly limited, and polyamide resin obtained from dicarboxylic acid and diamine,
Polyamides obtained from aminocarboxylic acids and lactams can be used. Specific examples include nylon 6, nylon 6.6, nylon 6.9, nylon 4.6, and nylon 6.10. , aliphatic polyamides such as nylon 6/12, nylon 11, and nylon 12, or aromatics obtained from aromatic dicarboxylic acids such as terephthalic acid and isophthalic acid, and aromatic diamines or aliphatic diamines such as metaxylylene diamine. polyamide, semi-aromatic polyamide, polyamide obtained from aromatic diamine such as metaxylylene diamine and aliphatic dicarboxylic acid, and copolymers and mixtures thereof.
C成分のカルボキシル基、酸無水物基、エポキシ基、カ
ルボン酸金属塩、酸無水物基力くイミド化物された官能
基、ヒドロキシル基及びアミノ基力Aら選ばれる少なく
とも1種の官能基で変性されたポリオレフィンの製造方
法は特に制限【まなし)力(、オレフィンとこれらの官
能基を有する不飽和単量体を共重合する方法、ポリオレ
フィン(ここれらの官能基を持つ単量体をグラフトする
方法等力く挙巳ヂられる。ここで使用されるオレフィン
として番よ、エチレン、〕知ピレレジブテン−1,4−
メチルペンテン−1等が挙げられ、酢酸ビニル、プロピ
オン酸ビニル等のビニルエステル類、ビニルエーテル類
等を共重合成分として含んでも良し)。またこれらと共
重合あるいはグラフトされる官能基を持った単量体とし
てはアクリル酸、メタクIJ )し酸等の不飽和モノカ
ルボン酸、マレイン酸、フマル酸、イタコン酸等の不飽
和ジカルボン酸およびそれらの無水物、アクリル酸グリ
シジル、メタクIJル酸グリシジル等の不飽和カルボン
酸り゛IJシジルエステル等がある。またマレイミド、
N−フェニルマレイミド等の不飽和ジカルボン酸のイミ
ド化物、ヒドロキシプロペン、ヒドロキシフ゛テン等の
不飽和アルコール等ヒドロキシル基と2重結合を有する
化合物、メタクリル酸アミノエチル、アクリルアミドア
リルアミン、アミノスチレン等のようにアミノ基を有す
るビニル系化合物等も好ましく用いられる。またこのよ
うにして得られた重合体をアイオノマー化したものも好
ましく使用できる。Modification with at least one functional group selected from carboxyl group, acid anhydride group, epoxy group, carboxylic acid metal salt, acid anhydride group, imidized functional group, hydroxyl group, and amino group of component C The methods for producing polyolefins are particularly limited, including methods for copolymerizing olefins and unsaturated monomers with these functional groups, and methods for grafting monomers with these functional groups on polyolefins. The olefins used here include ethylene, pyreredibutene-1,4-
Examples include methylpentene-1, and may also contain vinyl esters such as vinyl acetate and vinyl propionate, vinyl ethers, etc. as copolymerization components). Monomers with functional groups that can be copolymerized or grafted with these include unsaturated monocarboxylic acids such as acrylic acid and methacrylic acid; unsaturated dicarboxylic acids such as maleic acid, fumaric acid, and itaconic acid; Examples include anhydrides thereof, unsaturated carboxylic acid esters such as glycidyl acrylate, glycidyl methacrylate, and the like. Also maleimide,
Imidized products of unsaturated dicarboxylic acids such as N-phenylmaleimide, compounds having a hydroxyl group and a double bond such as unsaturated alcohols such as hydroxypropene and hydroxybutene, amino acids such as aminoethyl methacrylate, acrylamide allylamine, aminostyrene, etc. Vinyl compounds having groups are also preferably used. Furthermore, ionomerized polymers obtained in this manner can also be preferably used.
A成分の低粘度共重合体とB成分のポリアミド樹脂及び
C成分の変性ポリオレフィンの混合割合は低粘度共重合
体10〜80重量%、ポリアミド樹脂20〜90重量%
、変性ポリオレフィン1〜30重量%であり、低粘度共
重合体が10重量%未満では吸湿性改良に顕著な効果を
発揮できず、80重量%を越えると機械的強度に欠ける
材料となる。ポリアミド樹脂が20重量%未満では得ら
れる樹脂が脆くなり、90重量%を越えると吸湿性およ
び耐熱性に劣る。変性ポリオレフィンが1重量%未満で
は耐衝撃性に劣り、30重量%を越えると耐熱性が大幅
に低下し好ましくない。The mixing ratio of the low viscosity copolymer as component A, the polyamide resin as component B, and the modified polyolefin as component C is 10 to 80% by weight of the low viscosity copolymer and 20 to 90% by weight of the polyamide resin.
, the modified polyolefin is 1 to 30% by weight, and if the low viscosity copolymer is less than 10% by weight, it will not be able to exhibit a significant effect in improving hygroscopicity, and if it exceeds 80% by weight, the material will lack mechanical strength. If the polyamide resin content is less than 20% by weight, the resin obtained will be brittle, and if it exceeds 90% by weight, the hygroscopicity and heat resistance will be poor. If the modified polyolefin is less than 1% by weight, the impact resistance will be poor, and if it exceeds 30% by weight, the heat resistance will be significantly reduced, which is not preferred.
イミド化共重合体と有機過酸化物またはビベンジル誘導
体との溶融混練及び低粘度共重合体とポリアミド樹脂及
び変成ポリオレフィンとの溶融混線の方法には制限はな
く、ニーダ−1単軸または2軸以上の押出機等公知のも
のが使用できる。イミド化共重合体と有機過酸化物また
はビベンジル誘導体とを溶融混練し、得られた低粘度共
重合体をペレット化した後ポリアミド及び変性ポリオレ
フィンと混合しても良いし、2段混練機等を用いて低粘
度共重合体が溶融状態のうちにポリアミド及び変性ポリ
オレフィンを加えても良い。またイミド化共重合体、有
機過酸化物またはビヘンジル誘導体、ポリアミド及び変
性ポリオレフィンを同時に溶融混練しても本発明の熱可
塑性樹脂が得られる。There are no restrictions on the method of melt-kneading the imidized copolymer and the organic peroxide or bibenzyl derivative, and the melt-mixing method of the low-viscosity copolymer and the polyamide resin and modified polyolefin. A known extruder can be used, such as an extruder. The imidized copolymer and the organic peroxide or bibenzyl derivative may be melt-kneaded, the obtained low-viscosity copolymer may be pelletized, and then mixed with the polyamide and modified polyolefin, or a two-stage kneader or the like may be used. The polyamide and modified polyolefin may be added while the low viscosity copolymer is in a molten state. The thermoplastic resin of the present invention can also be obtained by simultaneously melt-kneading the imidized copolymer, organic peroxide or bihenzyl derivative, polyamide, and modified polyolefin.
また、本発明の熱可塑性樹脂に、酸化防止剤、難燃剤、
帯電防止剤、紫外線吸収剤、着色剤、可塑剤、滑剤、ガ
ラス繊維、カーボン繊維、炭酸カルシウム、タルク等を
添加することもできる。Further, the thermoplastic resin of the present invention may include antioxidants, flame retardants,
Antistatic agents, ultraviolet absorbers, colorants, plasticizers, lubricants, glass fibers, carbon fibers, calcium carbonate, talc, etc. can also be added.
〈実施例〉 以下、製造例、実施例によって本発明を説明する。<Example> The present invention will be explained below with reference to production examples and examples.
製造例1 低粘度共重合体(A−1,A−2)の製造
スチレン、N−フェニルマレイミド、及び無水マレイン
酸をそれぞれ43.6重量%、52.7重量%、3.7
重量%を含むイミド化共重合体(電気化学工業型MS−
L)100重量部に対し、2.3−ジメチル−2,3−
ジフエニルフ゛タン(日本油脂型ノフマーBC)を1.
4、及び2.8重量部の配合比で(第1表)、2軸押比
機(東洋精機製作新製2D25−5)を用いて290°
Cで溶融混練した。Production Example 1 Production of low viscosity copolymers (A-1, A-2) Styrene, N-phenylmaleimide, and maleic anhydride were 43.6% by weight, 52.7% by weight, and 3.7% by weight, respectively.
Imidized copolymer containing % by weight (Denki Kagaku Kogyo type MS-
L) 2,3-dimethyl-2,3- per 100 parts by weight
Diphenyl phethane (NOF-type NOFUMER BC) was added in 1.
At a blending ratio of 4 and 2.8 parts by weight (Table 1), a 290°
The mixture was melt-kneaded with C.
溶融した樹脂をストランド状に押し出し、そのストラン
ドをペレタイザーにてカッティングして、目的とする樹
脂を得た。得られたA−1、A−2の溶融粘度を、第2
表に示す。The molten resin was extruded into a strand, and the strand was cut with a pelletizer to obtain the desired resin. The melt viscosity of the obtained A-1 and A-2 was
Shown in the table.
製造例2 低粘度共重合体(A−3)の製造製造例1と
同様のイミド化共重合体(電気化学工業型MS−L)1
00重量部に対しキュメンハイドロパーオキサイド(日
本油脂製パークミルH)を0.5重量部(第1表)の配
合比で、製造例1と同様の処理を行い、目的とする樹脂
を得た。Production Example 2 Production of low viscosity copolymer (A-3) Imidized copolymer (Denki Kagaku Kogyo type MS-L) 1 similar to Production Example 1
The same treatment as in Production Example 1 was carried out at a blending ratio of 0.00 parts by weight to 0.5 parts by weight of cumene hydroperoxide (Percumyl H manufactured by NOF Co., Ltd. (Table 1)) to obtain the desired resin.
得られたA−3の溶融粘度を第2表に示す。The melt viscosity of the obtained A-3 is shown in Table 2.
実施例1
低粘度共重合体A−1、ナイロン6(宇部興産型101
3B)及びエチレン・アクリル酸共重合体亜鉛塩(三井
・デュポンポリケミカル社製ハイミラン1s55)を表
2の割合で混合し、2軸押比機(東洋精機製作新製2D
25−3)を用いて290℃で溶融混練した。Example 1 Low viscosity copolymer A-1, nylon 6 (Ube Industries type 101)
3B) and ethylene/acrylic acid copolymer zinc salt (Himilan 1s55, manufactured by DuPont Mitsui Polychemicals) in the proportions shown in Table 2, a two-screw presser (newly manufactured by Toyo Seiki Co., Ltd. 2D) was mixed.
25-3) at 290°C.
溶融した樹脂をストランド状に押し出し、そのストラン
ドをペレタイザーにてカッティングして目的とする樹脂
を得た。得られた樹脂組成物の引っ張り伸度をASTM
規格D−638に従い測定した。The molten resin was extruded into a strand, and the strand was cut with a pelletizer to obtain the desired resin. The tensile elongation of the obtained resin composition was determined by ASTM
Measured according to standard D-638.
実施例2
変性ポリオレフィンを無水マレイン酸変性EPR(日本
合成ゴム社製T7761P)に変え、実施例1と同様の
操作を行った。Example 2 The same operation as in Example 1 was performed except that the modified polyolefin was replaced with maleic anhydride-modified EPR (T7761P manufactured by Japan Synthetic Rubber Co., Ltd.).
実施例3
変性ポリオレフィンをエチレン・グリシジルメタクリレ
ート共重合体(住友化学工業製ボンドファース1−E)
に変え、実施例1.2と同様の操作を行った。Example 3 Modified polyolefin was converted into ethylene glycidyl methacrylate copolymer (Bondfirth 1-E manufactured by Sumitomo Chemical Industries)
, and the same operation as in Example 1.2 was performed.
実施例4〜6
低粘度共重合体をA−2,A−3に変えて、実施例3と
同様の操作を行った。Examples 4 to 6 The same operation as in Example 3 was performed except that the low viscosity copolymers were changed to A-2 and A-3.
実施例7
ポリアミドをナイロン12(宇部興産型)に変えて、同
様の操作を行った。Example 7 The same operation was carried out by changing the polyamide to nylon 12 (Ube Industries type).
比較例1
製造例1で用いたイミド化共重合体(電気化学工業型M
S−L) 、ナイロン6(宇部興産型1013B)及び
エチレン・アクリル酸共重合体亜鉛塩(三井・デュポン
ポリケミカル社製ハイミラン1855)を表4の割合で
混合し、2軸押比機(東洋精機製作新製2D25−3)
を用いて290℃で溶融混練し実施例1と同様の評価を
行った。Comparative Example 1 Imidized copolymer used in Production Example 1 (Denki Kagaku Kogyo type M
S-L), nylon 6 (Ube Industries type 1013B), and ethylene-acrylic acid copolymer zinc salt (Himilan 1855 manufactured by DuPont Mitsui Polychemicals) were mixed in the proportions shown in Table 4, and a twin-screw presser (Toyo Seiki Seizo Shinsei 2D25-3)
The mixture was melt-kneaded at 290° C. and evaluated in the same manner as in Example 1.
比較例2
ポリオレフィンをエチレン・グリシジルメタクリレート
共重合体(住友化学工業製ボンドファーストE)に変え
、比較例1と同様の操作を行った。Comparative Example 2 The same operation as in Comparative Example 1 was performed except that the polyolefin was replaced with an ethylene/glycidyl methacrylate copolymer (Bond Fast E manufactured by Sumitomo Chemical Industries).
実施例1〜7及び比較例1〜2の評価結果を第2表にま
とめて示す。The evaluation results of Examples 1 to 7 and Comparative Examples 1 to 2 are summarized in Table 2.
第 表 傘沌曙曽υ飯徂ごできず。No. table Umbrella Chaos Akebono I couldn't get it.
沌奸拠切し々咄m斐300°c、」駐欣控斐6X 10
”α〔1で測定した〈発明の効果〉
前述の通り、本発明で開示された、あらかじめ特定の化
合物と溶融混練して低粘度化された特定のイミド化共重
合体と、特定のポリアミド及び、特定の変性ポリオレフ
ィンを溶融混練することにより、分散性のよいポリマー
ブレンド物を得ることができる。しかもこの熱可塑性樹
脂は強靭性を保持しているため、自動車部品、電気部品
、その他建材雑貨部品などの用途に好適に使用すること
ができる。300°C Chaotic Forces, Garrison Control 6X 10
"Effect of the invention measured by α [1] As mentioned above, the specific imidized copolymer disclosed in the present invention, which has been melt-kneaded in advance with a specific compound to reduce the viscosity, and the specific polyamide and By melt-kneading specific modified polyolefins, it is possible to obtain polymer blends with good dispersibility.Furthermore, this thermoplastic resin maintains its toughness, so it can be used for automobile parts, electrical parts, and other building materials and miscellaneous parts. It can be suitably used for purposes such as.
Claims (1)
不飽和ジカルボン酸イミド誘導体0〜60重量%、不飽
和ジカルボン酸無水物単量体1〜10重量%、及びそれ
らと共重合可能な他の不飽和ビニル誘導体0〜40重量
%とからなるイミド化共重合体100重量部と、下記(
1)式または(2)式で表される有機過酸化物または下
記(3)式で表されるビベンジル誘導体0.1〜10重
量部を溶融混練して得られる低粘度熱可塑性樹脂10〜
80重量%と R^1−O−O−R^2(1) R^1−O−O−X−O−O−R^2(2)(式中、R
^1、R^2は、各々水素原子、又は、ハロゲン原子、
または炭素数1〜5の直鎖または分岐アルキル基、また
はシクロアルキル基、またはアリール基、または置換ア
リール基を表し、Xは炭素数1〜10の飽和または不飽
和の直鎖または分岐の2価の原子団、または芳香環を含
む炭素数6〜15の2価の原子団を表す。) ▲数式、化学式、表等があります▼(3) (式中、R^1、R^2、R^3及びR^4は各々水素
原子、またはハロゲン原子、または炭素数1〜5の直鎖
または分岐アルキル基、またはシクロアルキル基または
アリール基、または置換アリール基を表す。) B成分:ポリアミド樹脂20〜90重量%及び、C成分
:カルボキシル基、酸無水物基、エポキシ基、カルボン
酸金属塩基、ヒドロキシル基及びアミノ基から選ばれる
少なくとも1種の官能基で変性されたポリオレフィン1
〜30重量%を溶融混練してなることを特徴とする熱可
塑性樹脂組成物。(1) Component A: 30 to 70% by weight of aromatic vinyl monomer,
Imidization consisting of 0 to 60% by weight of an unsaturated dicarboxylic acid imide derivative, 1 to 10% by weight of an unsaturated dicarboxylic anhydride monomer, and 0 to 40% by weight of another unsaturated vinyl derivative copolymerizable with them. 100 parts by weight of copolymer and the following (
10 to 10 parts by weight of a low-viscosity thermoplastic resin obtained by melt-kneading 0.1 to 10 parts by weight of an organic peroxide represented by the formula (1) or (2) or a bibenzyl derivative represented by the following formula (3)
80% by weight and R^1-O-O-R^2(1) R^1-O-O-X-O-O-R^2(2) (in the formula, R
^1 and R^2 are each a hydrogen atom or a halogen atom,
or represents a straight chain or branched alkyl group having 1 to 5 carbon atoms, a cycloalkyl group, an aryl group, or a substituted aryl group, and X is a saturated or unsaturated straight chain or branched divalent group having 1 to 10 carbon atoms. or a divalent atomic group having 6 to 15 carbon atoms and containing an aromatic ring. ) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(3) (In the formula, R^1, R^2, R^3, and R^4 are each a hydrogen atom, a halogen atom, or a straight carbon number of 1 to 5. Represents a chain or branched alkyl group, cycloalkyl group, aryl group, or substituted aryl group.) Component B: 20 to 90% by weight of polyamide resin, and Component C: carboxyl group, acid anhydride group, epoxy group, carboxylic acid. Polyolefin 1 modified with at least one functional group selected from a metal base, a hydroxyl group, and an amino group
A thermoplastic resin composition characterized by being formed by melt-kneading ~30% by weight.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23253990A JPH04114052A (en) | 1990-09-04 | 1990-09-04 | Thermoplastic resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP23253990A JPH04114052A (en) | 1990-09-04 | 1990-09-04 | Thermoplastic resin composition |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH04114052A true JPH04114052A (en) | 1992-04-15 |
Family
ID=16940916
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP23253990A Pending JPH04114052A (en) | 1990-09-04 | 1990-09-04 | Thermoplastic resin composition |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH04114052A (en) |
-
1990
- 1990-09-04 JP JP23253990A patent/JPH04114052A/en active Pending
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