JPH044204A - Epoxidized low-molecular weight ethylene-alpha-olefin copolymer and thermoplastic resin composition - Google Patents
Epoxidized low-molecular weight ethylene-alpha-olefin copolymer and thermoplastic resin compositionInfo
- Publication number
- JPH044204A JPH044204A JP10464390A JP10464390A JPH044204A JP H044204 A JPH044204 A JP H044204A JP 10464390 A JP10464390 A JP 10464390A JP 10464390 A JP10464390 A JP 10464390A JP H044204 A JPH044204 A JP H044204A
- Authority
- JP
- Japan
- Prior art keywords
- molecular weight
- ethylene
- copolymer
- olefin
- conjugated diene
- 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
- 239000004711 α-olefin Substances 0.000 title claims abstract description 35
- 239000011342 resin composition Substances 0.000 title claims abstract description 16
- 229920005992 thermoplastic resin Polymers 0.000 title claims description 24
- 229920000089 Cyclic olefin copolymer Polymers 0.000 title claims description 19
- 229920001577 copolymer Polymers 0.000 claims abstract description 50
- 150000001993 dienes Chemical class 0.000 claims abstract description 18
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000005977 Ethylene Substances 0.000 claims abstract description 16
- 239000004793 Polystyrene Substances 0.000 claims abstract description 10
- 229920002223 polystyrene Polymers 0.000 claims abstract description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 5
- 239000011630 iodine Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000000203 mixture Substances 0.000 abstract description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 7
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 abstract description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 abstract description 5
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 abstract description 4
- 238000000465 moulding Methods 0.000 abstract description 4
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 238000010526 radical polymerization reaction Methods 0.000 abstract 1
- -1 polypropylene Polymers 0.000 description 40
- 229920001971 elastomer Polymers 0.000 description 29
- 229920005989 resin Polymers 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- 229920002943 EPDM rubber Polymers 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 125000003700 epoxy group Chemical group 0.000 description 14
- 229920000728 polyester Polymers 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000003607 modifier Substances 0.000 description 13
- 229920001169 thermoplastic Polymers 0.000 description 12
- 239000004416 thermosoftening plastic Substances 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 229920001955 polyphenylene ether Polymers 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000000379 polymerizing effect Effects 0.000 description 6
- 229920006324 polyoxymethylene Polymers 0.000 description 6
- 239000005060 rubber Substances 0.000 description 6
- 239000000565 sealant Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229930182556 Polyacetal Natural products 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 229920003048 styrene butadiene rubber Polymers 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 235000019253 formic acid Nutrition 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 229920000515 polycarbonate Polymers 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 229920001707 polybutylene terephthalate Polymers 0.000 description 3
- 238000012643 polycondensation polymerization Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 2
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- HFDVRLIODXPAHB-UHFFFAOYSA-N 1-tetradecene Chemical compound CCCCCCCCCCCCC=C HFDVRLIODXPAHB-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-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
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- LABJFIBQJFPXHZ-UHFFFAOYSA-N 4-(carboxymethoxy)benzoic acid Chemical compound OC(=O)COC1=CC=C(C(O)=O)C=C1 LABJFIBQJFPXHZ-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- WSSSPWUEQFSQQG-UHFFFAOYSA-N 4-methyl-1-pentene Chemical compound CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 229920001893 acrylonitrile styrene Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920006026 co-polymeric resin Polymers 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000010687 lubricating oil Substances 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- BNJOQKFENDDGSC-UHFFFAOYSA-N octadecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCCC(O)=O BNJOQKFENDDGSC-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920000090 poly(aryl ether) Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000412 polyarylene Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229920003051 synthetic elastomer Polymers 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- KQBSGRWMSNFIPG-UHFFFAOYSA-N trioxane Chemical compound C1COOOC1 KQBSGRWMSNFIPG-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OJOWICOBYCXEKR-APPZFPTMSA-N (1S,4R)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound CC=C1C[C@@H]2C[C@@H]1C=C2 OJOWICOBYCXEKR-APPZFPTMSA-N 0.000 description 1
- PRBHEGAFLDMLAL-GQCTYLIASA-N (4e)-hexa-1,4-diene Chemical compound C\C=C\CC=C PRBHEGAFLDMLAL-GQCTYLIASA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N 1,4-butanediol Substances OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-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
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-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
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- GELKGHVAFRCJNA-UHFFFAOYSA-N 2,2-Dimethyloxirane Chemical compound CC1(C)CO1 GELKGHVAFRCJNA-UHFFFAOYSA-N 0.000 description 1
- CYLVUSZHVURAOY-UHFFFAOYSA-N 2,2-dibromoethenylbenzene Chemical compound BrC(Br)=CC1=CC=CC=C1 CYLVUSZHVURAOY-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
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-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
- WROUWQQRXUBECT-UHFFFAOYSA-M 2-ethylacrylate Chemical compound CCC(=C)C([O-])=O WROUWQQRXUBECT-UHFFFAOYSA-M 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
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- ATJCASULPHYKHT-UHFFFAOYSA-N hexadecane-1,16-diamine Chemical compound NCCCCCCCCCCCCCCCCN ATJCASULPHYKHT-UHFFFAOYSA-N 0.000 description 1
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- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- FSAJWMJJORKPKS-UHFFFAOYSA-N octadecyl prop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C=C FSAJWMJJORKPKS-UHFFFAOYSA-N 0.000 description 1
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Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野］
本発明はエポキシ化低分子量エチレン−α−オレフィン
共重合体および熱可塑性樹脂組成物に関し、さらに詳し
くは各種ゴム状または樹脂状重合体の改質剤または改質
助剤、接着剤、シーラント、ルーフィング剤等として好
適な新規なエポキシ化低分子量エチレン−α−オレフィ
ン共重合体および該共重合体を用いた、耐衝撃性、成形
加工性および成形品表面性に優れた熱可塑性樹脂組成物
に関する。Detailed Description of the Invention [Field of Industrial Application] The present invention relates to epoxidized low molecular weight ethylene-α-olefin copolymers and thermoplastic resin compositions, and more particularly to the modification of various rubbery or resinous polymers. A novel epoxidized low molecular weight ethylene-α-olefin copolymer suitable as a modifying agent or a modification aid, an adhesive, a sealant, a roofing agent, etc., and impact resistance, moldability and The present invention relates to a thermoplastic resin composition with excellent surface properties of molded products.
従来、エチレン−α−オレフィン−非共役ジエン共重合
体をエポキシ化した変性オレフィン系重合体は公知であ
る（特開昭６０−１６８７５０号公報）。しかし、該変
性共重合体は高分子量であるため、ゴムや樹脂などへの
分散性に劣り、また接着剤、シーラント、ルーフィング
剤として用いた場合、流動性に乏しいため、充分な性能
をが得られないという欠点がある。一方、未変性の低分
子量エチレン−α−オレフィン共重合体は、無極性であ
るため、極性ゴムや極性樹脂に対する相溶性が低く、改
質剤としての性能に劣る欠点がある。Hitherto, a modified olefin polymer obtained by epoxidizing an ethylene-α-olefin-nonconjugated diene copolymer has been known (Japanese Patent Laid-Open No. 168750/1983). However, because the modified copolymer has a high molecular weight, it has poor dispersibility in rubbers and resins, and when used as adhesives, sealants, and roofing agents, it has poor fluidity, so it is difficult to obtain sufficient performance. The disadvantage is that it cannot be used. On the other hand, since unmodified low molecular weight ethylene-α-olefin copolymers are non-polar, they have a drawback of low compatibility with polar rubbers and polar resins, and poor performance as modifiers.
また特開昭６３−３０５１０４号公報には、末端の二重
結合をエポキシ化した変性低分子量エチレン−α−オレ
フィン共重合体が示されているが、この変性共重合体は
１分子中に１個のエポキシ基しか存在しないため、高極
性のエポキシ化エチレン−α−オレフィン共重合体を得
るためには極低分子量としなければならず、またエポキ
シ基が末端のみに存在するため、エポキシ基同士の架橋
反応は起こらないので分散効果が劣る。Furthermore, JP-A-63-305104 discloses a modified low molecular weight ethylene-α-olefin copolymer in which the terminal double bond is epoxidized. Since there are only 3 epoxy groups, the molecular weight must be extremely low in order to obtain a highly polar epoxidized ethylene-α-olefin copolymer.Also, since epoxy groups exist only at the ends, the epoxy groups Since the crosslinking reaction does not occur, the dispersion effect is poor.
さらに、従来、ポリプロピレン、ＡＳ樹脂、熱可塑性ポ
リエステル、ポリアミド等の熱可塑性樹脂は、優れた機
械的強度、電気的特性、耐薬品性、成形加工性および成
形品表面性に優れるため、自動車分野、電気電子分野等
に幅広く使用されている。これらの樹脂はノツチ（切込
み）を付けた後の耐衝撃性に劣るため、改質剤としてゴ
ム質重合体や可塑化剤などを配合する方法がとられてい
る。Furthermore, conventionally, thermoplastic resins such as polypropylene, AS resin, thermoplastic polyester, and polyamide have excellent mechanical strength, electrical properties, chemical resistance, molding processability, and molded product surface properties, so they are used in the automotive field. Widely used in electrical and electronic fields. Since these resins have poor impact resistance after notching, a method of blending rubbery polymers, plasticizers, etc. as modifiers has been adopted.
しかしながら、ゴム質重合体を用いた場合、耐衝撃性は
改良されるが、成形加工性に劣る欠点があり、また可塑
化剤を用いた場合には、成形品の表面上に可塑化剤が浮
き出てくるため表面性が低下するという欠点がある。However, when a rubbery polymer is used, the impact resistance is improved, but it has the disadvantage of poor moldability, and when a plasticizer is used, the plasticizer remains on the surface of the molded product. It has the disadvantage that the surface quality deteriorates because it stands out.
最近、種々の樹脂またはゴム状重合体の改質剤、改質助
剤、接着剤、シーラント、ルーフィング剤等の高性能化
が要求されている。Recently, there has been a demand for improved performance of modifiers, modifiers, adhesives, sealants, roofing agents, etc. for various resins or rubber-like polymers.
〔発明が解決しようとする課題］
本発明の第１の目的は、前記従来技術の欠点をなくし、
各種樹脂またはゴム状重合体の改質剤および改質助剤と
して用いた場合の分散性に優れ、かつ接着剤、シーラン
トおよびルーフィング剤として優れた性能を有するエポ
キシ化低分子量エチレン−α−オレフィン共重合体を提
供することにある。[Problems to be Solved by the Invention] The first object of the present invention is to eliminate the drawbacks of the prior art,
Epoxidized low molecular weight ethylene-α-olefins with excellent dispersibility when used as modifiers and modifiers for various resins or rubbery polymers, and excellent performance as adhesives, sealants, and roofing agents. The purpose is to provide a polymer.
本発明の第２の目的は、上記エポキシ化低分子量エチレ
ン−α−オレフィン共重合体を用いて耐衝撃性、成形加
工性および成形品表面性に優れた熱可塑性樹脂組成物を
提供することにある。A second object of the present invention is to provide a thermoplastic resin composition that uses the above-mentioned epoxidized low molecular weight ethylene-α-olefin copolymer and has excellent impact resistance, moldability, and surface properties of molded products. be.
本発明の第１は、（Ａ）エチレン成分含量が３０〜７５
モル％およびα−オレフィン成分含量が７０〜２５モル
％、（Ｂ）非共役ジエン成分含量がヨウ素価で３〜１０
０ならびに（Ｃ）ポリスチレン換算重量平均分子量が３
００〜５０，０００である、エチレンと炭素数３〜２０
のα−オレフィンと非共役ジエンとからなるランダム低
分子量共重合体（以下、単に「低分子量共重合体」とい
う）中の非共役ジエン成分の二重結合の１％以上をエポ
キシ化してなるエポキシ化低分子量エチレン−α−オレ
フィン共重合体（以下、単に「エポキシ化低分子量共重
合体」という）に関する。The first aspect of the present invention is that (A) the ethylene component content is 30 to 75
Mol% and α-olefin component content are 70 to 25 mol%, (B) non-conjugated diene component content is 3 to 10 in terms of iodine value.
0 and (C) polystyrene equivalent weight average molecular weight is 3
00-50,000, ethylene and carbon number 3-20
Epoxy obtained by epoxidizing 1% or more of the double bonds of the non-conjugated diene component in a random low-molecular-weight copolymer (hereinafter simply referred to as "low-molecular-weight copolymer") consisting of an α-olefin and a non-conjugated diene. epoxidized low molecular weight ethylene-α-olefin copolymer (hereinafter simply referred to as "epoxidized low molecular weight copolymer").
本発明の第２は、熱可塑性樹脂１００重量部、上記エポ
キシ化低分子量共重合体１〜８０重量部および高分子量
エチレン−α−オレフィン共重合体０〜８０重量部を含
有してなる熱可塑性樹脂組成物に関する。The second aspect of the present invention is a thermoplastic resin containing 100 parts by weight of a thermoplastic resin, 1 to 80 parts by weight of the above-mentioned epoxidized low molecular weight copolymer, and 0 to 80 parts by weight of a high molecular weight ethylene-α-olefin copolymer. The present invention relates to a resin composition.
第１の発明に用いられる低分子量共重合体は、エチレン
と炭素数３〜２０のα−オレフィンと非共役ジエンとか
らなり、（Ａ）エチレン成分［（−ＣＨ２ＣＨ２＋で表
されるエチレン単位］含量が３０〜７５モル％、好まし
くは４０〜７０モル％およびα−オレフィン成分Ｃ＋Ｃ
Ｈ２８Ｈ＋で表されるα−オレフィン単位、但しＲは炭
素数１〜１８のアルキル基を示す〕含量が７０〜２５モ
ル％、好ましくは６０〜３０モル％、（Ｂ）非共役ジエ
ン成分含量がヨウ素価で３〜１００、好ましくは１０〜
８０ならびに（Ｃ）ゲルパーミエイションクロマトグラ
フィー（ＧＰＣ）によるポリスチレン換算重量平均分子
量（Ｍｗ）が３００〜５０ ０００、好ましくは１，０
００〜３０，０００である共重合体である。分子量分布
［Ｍｗ／Ｍｎ（ポリスチレン換算数平均分子量）］は４
以下が好ましく、１．２〜３．５がより好ましい。Ｍｗ
が３００未満では配合物の機械的強度を低下させ、５０
，０００を超えると流動性が劣る。また上記範囲外の共
重合体では、各種樹脂またはゴム状重合体の改質剤等と
して用いた場合の力学的物性の改善効果に劣る。The low molecular weight copolymer used in the first invention consists of ethylene, an α-olefin having 3 to 20 carbon atoms, and a non-conjugated diene, and includes (A) an ethylene component [ethylene units represented by -CH2CH2+] content; is 30 to 75 mol%, preferably 40 to 70 mol% and α-olefin component C+C
α-olefin unit represented by H28H+, where R represents an alkyl group having 1 to 18 carbon atoms] content is 70 to 25 mol%, preferably 60 to 30 mol%, (B) non-conjugated diene component content is iodine Value of 3 to 100, preferably 10 to 100
80 and (C) polystyrene equivalent weight average molecular weight (Mw) measured by gel permeation chromatography (GPC) of 300 to 50 000, preferably 1.0
00 to 30,000. Molecular weight distribution [Mw/Mn (polystyrene equivalent number average molecular weight)] is 4
The following are preferable, and 1.2 to 3.5 are more preferable. Mw
If it is less than 300, the mechanical strength of the compound will be reduced;
,000, the fluidity is poor. Further, copolymers outside the above range are inferior in the effect of improving mechanical properties when used as a modifier for various resins or rubber-like polymers.
炭素数３〜２０のα−オレフィンとしては、プロピレン
、１−ブテン、ｌ−ヘキセン、４−メチル−１−ペンテ
ン、３−メチル−１−ペンテン、ｌ−オクテン、１−デ
セン、ｌ−ドデセン、１テトラデセン、１−へキサデセ
ン、■−オクタデセン、１−エイコセンなどが用いられ
る。該αオレフィンの使用量は低分子量共重合体に対し
て２５〜７０モル％が好ましく、より好ましくは３０〜
６０モル％の範囲である。Examples of α-olefins having 3 to 20 carbon atoms include propylene, 1-butene, 1-hexene, 4-methyl-1-pentene, 3-methyl-1-pentene, 1-octene, 1-decene, 1-dodecene, 1-tetradecene, 1-hexadecene, -octadecene, 1-eicosene, etc. are used. The amount of the α-olefin used is preferably 25 to 70 mol%, more preferably 30 to 70 mol%, based on the low molecular weight copolymer.
It is in the range of 60 mol%.
非共役ジエンとしては、１．４−ヘキサジエン、ジシク
ロペンタジェン、５−エチリデン−２−ノルボルネン、
２，５−ノルボルナジェン、２−メチル−２，７−オク
タジエン等が用いられる。これらのうちエポキシ化の反
応性を向上させる点から、ジシクロペンタジェンが好ま
しい。Non-conjugated dienes include 1,4-hexadiene, dicyclopentadiene, 5-ethylidene-2-norbornene,
2,5-norbornadiene, 2-methyl-2,7-octadiene, etc. are used. Among these, dicyclopentadiene is preferred from the viewpoint of improving the reactivity of epoxidation.
上記低分子量共重合体は、エチレン、α−オレフィンお
よび非共役ジエンを、−船釣な遷移金属化合物と有機金
属化合物とからなるチーグラーナツタ型触媒系、例えば
バナジウムと有機アルミニウム、チタンと有機アルミニ
ウム等の存在下で公知の方法で合成することができる。The low molecular weight copolymer is a Ziegler-Natsuta type catalyst system consisting of ethylene, an α-olefin and a non-conjugated diene, and a transition metal compound and an organometallic compound, such as vanadium and organoaluminium, titanium and organoaluminum, etc. It can be synthesized by a known method in the presence of.
第１の発明であるエポキシ化低分子量共重合体は、上記
低分子量共重合体中の非共役ジエン成分の二重結合の１
％以上、好ましくは１０％以上、より好ましくは２０％
以上をエポキシ化して得られる共重合体である。エポキ
シ化が１％未満では各種樹脂またはゴム状重合体の改質
剤等として用いた場合の力学的物性の改善効果に劣る。The epoxidized low molecular weight copolymer of the first invention is characterized in that one of the double bonds of the non-conjugated diene component in the low molecular weight copolymer is
% or more, preferably 10% or more, more preferably 20%
This is a copolymer obtained by epoxidizing the above. If the epoxidation content is less than 1%, the effect of improving mechanical properties when used as a modifier for various resins or rubber-like polymers is poor.
低分子量共重合体のエポキシ化は、例えば（１）低分子
量共重合体と、蟻酸、酢酸等の有機酸と、過酸化水素水
との混合物を反応させる方法、（２）低分子量共重合体
と、ｍ−クロロ過安息香酸、過安息香酸等の有機過酸化
物とを反応させる方法などにより行うことができる。Epoxidation of a low molecular weight copolymer can be carried out by, for example, (1) a method of reacting a mixture of a low molecular weight copolymer, an organic acid such as formic acid or acetic acid, and aqueous hydrogen peroxide; (2) a method of reacting a low molecular weight copolymer with an organic acid such as formic acid or acetic acid; This can be carried out by a method of reacting with an organic peroxide such as m-chloroperbenzoic acid or perbenzoic acid.
前者の方法の場合、低分子量共重合体は塊状のまま、ま
たは例えばトルエン、キシレン、ベンゼン等の芳香族炭
化水素、ヘキサン、ヘプタン、オクタン等の飽和炭化水
素などの有機溶媒に溶解して５〜５０％溶液として用い
られる。有機酸の使用量は、通常、低分子量共重合体中
の二重結合に対して０．２〜２．０倍モル、好ましくは
０．４〜１．７倍モルであり、また過酸化水素水の使用
量は、通常、低分子量共重合体中の二重結合に対して１
．０〜５．０倍モルとされる。これらの混合液を例えば
１０〜６０°Ｃの温度で１〜１０時間撹拌して反応する
ことにより、エポキシ化低分子量エチレン系ランダム共
重合体が得られる。In the case of the former method, the low-molecular-weight copolymer is either left in bulk or dissolved in an organic solvent such as an aromatic hydrocarbon such as toluene, xylene, benzene, or a saturated hydrocarbon such as hexane, heptane, or octane. Used as a 50% solution. The amount of organic acid used is usually 0.2 to 2.0 times the mole, preferably 0.4 to 1.7 times the mole of double bonds in the low molecular weight copolymer. The amount of water used is usually 1% per double bond in the low molecular weight copolymer.
．． 0 to 5.0 times the mole. An epoxidized low molecular weight ethylene random copolymer can be obtained by stirring and reacting these mixed liquids at a temperature of, for example, 10 to 60°C for 1 to 10 hours.
後者の方法の場合は、例えば低分子量共重合体を塩化メ
チレンなどのハロゲン化炭化水素の５〜５０％溶液とし
、これに有機過酸を低分子量共重合体中の二重結合に対
して０．０１〜１．５０倍モル、好ましくは０．１〜１
．２０倍モル加え、室温で１〜１０時間反応させること
により、エポキシ化低分子量共重合体が得られる。In the case of the latter method, for example, the low molecular weight copolymer is prepared as a 5 to 50% solution of a halogenated hydrocarbon such as methylene chloride, and an organic peracid is added to the solution to reduce the double bonds in the low molecular weight copolymer. .01 to 1.50 times mole, preferably 0.1 to 1
．． An epoxidized low molecular weight copolymer can be obtained by adding 20 times the mole amount and reacting at room temperature for 1 to 10 hours.
第１の発明になるエポキシ化低分子量共重合体は、共重
合体１分子中にエポキシ基を多数有し、高い極性を有す
るため、ゴムや樹脂などへの分散性に優れ、これらの改
質剤や改質助剤として、また潤滑油添加剤、水性分散剤
の分散助剤等として、また塗料およびその改質剤、接着
剤、シーラント、ルーフィング剤等として優れた性能を
有する。またエポキシ基同士の架橋反応が可能である。The epoxidized low molecular weight copolymer of the first invention has many epoxy groups in one molecule of the copolymer and has high polarity, so it has excellent dispersibility in rubbers, resins, etc., and is suitable for modification of these. It has excellent performance as a lubricating oil additive, a dispersion aid for aqueous dispersants, a paint and its modifier, an adhesive, a sealant, a roofing agent, etc. Furthermore, crosslinking reactions between epoxy groups are possible.
さらに後記する熱可塑性樹脂組成物の成分として用いる
ことにより耐衝撃性、成形加工性および成形品表面性を
改良することができる。Furthermore, by using it as a component of a thermoplastic resin composition described later, impact resistance, molding processability, and surface properties of molded products can be improved.
第２の発明である熱可塑性樹脂組成物は、熱可塑性樹脂
１００重量部および上記エポキシ化低分子量共重合体１
〜８０重量部、好ましくは２〜６０重量部を必須成分と
して含む。この組成物にはさらにゴム状重合体として高
分子量エチレン−α−オレフィン共重合体を０〜８０重
量部、好ましくは０〜６０重量部の範囲で含有すること
ができる。エポキシ化低分子量共重合体の使用量が、上
記範囲以外では、熱可塑性樹脂組成物の耐衝撃性、成形
加工性および成形品表面性の改良効果に劣る。The thermoplastic resin composition of the second invention comprises 100 parts by weight of a thermoplastic resin and 1 part by weight of the epoxidized low molecular weight copolymer.
~80 parts by weight, preferably 2 to 60 parts by weight, as an essential component. The composition may further contain a high molecular weight ethylene-α-olefin copolymer as a rubbery polymer in an amount of 0 to 80 parts by weight, preferably 0 to 60 parts by weight. If the amount of the epoxidized low molecular weight copolymer used is outside the above range, the effects of improving the impact resistance, moldability and surface properties of molded products of the thermoplastic resin composition will be poor.
第２の発明に用いられる熱可塑性樹脂としては、ポリス
チレン、ＡＳ樹脂、（メタ）アクリル酸アルキルエステ
ル−スチレン共重合樹脂、耐衝撃性ポリスチレン、ＡＢ
Ｓ樹脂、ＭＢＳ樹脂等のスチレン系樹脂、ポリエチレン
、ポリプロピレン等のオレフィン系樹脂、塩化ビニル樹
脂、酢酸ビニル樹脂等のビニル系樹脂、熱可塑性ポリエ
ステル、ポリアミド、ポリアリールエーテル、ポリスル
ホン、ポリカーボネート、ポリアセタール、熱可塑性イ
ソ・シアネート樹脂、ポリフェニレンエーテル、熱可塑
性尿素樹脂、ポリアリーレンスルフィド、ポリイミド、
ポリアリーレンケトンなどが挙げられる。これらの熱可
塑性樹脂は１種または２種以上で使用される。The thermoplastic resin used in the second invention includes polystyrene, AS resin, (meth)acrylic acid alkyl ester-styrene copolymer resin, high-impact polystyrene, AB
Styrene resins such as S resin and MBS resin, olefin resins such as polyethylene and polypropylene, vinyl resins such as vinyl chloride resin and vinyl acetate resin, thermoplastic polyester, polyamide, polyarylether, polysulfone, polycarbonate, polyacetal, heat Plastic iso-cyanate resin, polyphenylene ether, thermoplastic urea resin, polyarylene sulfide, polyimide,
Examples include polyarylene ketones. These thermoplastic resins may be used alone or in combination of two or more.
前記（メタ）アクリル酸アルキルエステル−スチレン共
重合樹脂に用いられる（メタ）アクリル酸アルキルエス
テルとしては、メチルアクリレート、エチルアクリレー
ト、プロピルアクリレート、ブチルアクリレート、アミ
ルアクリレート、ヘキシルアクリレート、オクチルアク
リレート、２−エチルへキシルアクリレート、シクロへ
キシルアクリレート、ドデシルアクリレート、オクタデ
シルアクリレート、フェニルアクリレート、ベンジルア
クリレート等のアクリル酸アルキルエステル、メチルメ
タクリレート、エチルメタクリレート、ブチルメタクリ
レート、アミルメタクリレート、ヘキシルメタクリレー
ト、オクチルメタクリレート、２−エチルへキシルメタ
クリレート、シクロへキシルメタクリレート、ドデシル
メタクリレート、オクタデシルメタクリレート、フェニ
ルメタクリレート、ベンジルメタクリレート等のメタク
リル酸アルキルエステルなどが挙げられ、これらは、１
種または２種以上で使用される。The (meth)acrylic acid alkyl ester used in the (meth)acrylic acid alkyl ester-styrene copolymer resin includes methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, amyl acrylate, hexyl acrylate, octyl acrylate, and 2-ethyl acrylate. Acrylic acid alkyl esters such as hexyl acrylate, cyclohexyl acrylate, dodecyl acrylate, octadecyl acrylate, phenyl acrylate, benzyl acrylate, methyl methacrylate, ethyl methacrylate, butyl methacrylate, amyl methacrylate, hexyl methacrylate, octyl methacrylate, 2-ethylhexyl Examples include methacrylic acid alkyl esters such as methacrylate, cyclohexyl methacrylate, dodecyl methacrylate, octadecyl methacrylate, phenyl methacrylate, and benzyl methacrylate;
Used in one species or in combination of two or more.
前記耐衝撃性ポリスチレン、ＡＢＳ樹脂またはＭＢＳ樹
脂は、通常、ゴム質重合体の存在下で重合されたものが
用いられる。これらのゴム変性樹脂中のゴム質重合体の
割合は、通常１〜７０重量％、好ましくは５〜６０重量
％とされる。The impact-resistant polystyrene, ABS resin, or MBS resin is usually polymerized in the presence of a rubbery polymer. The proportion of the rubbery polymer in these rubber-modified resins is usually 1 to 70% by weight, preferably 5 to 60% by weight.
該ゴム質重合体としては、ポリブタジェン、スチレン−
ブタジェン共重合体、アクリロニトリル−ブタジェン共
重合体、スチレン−ブタジェンブロック共重合体、水素
化スチレン−ブタジェンブロック共重合体、水素化スチ
レン−ブタジェンランダム共重合体、水素化アクリロニ
トリル−ブタジェン共重合体、α−オレフィンとしてプ
ロピレン、ブテン−１１ペンテン−１１ヘキセン−１１
へブテン−１，４−メチルペンテン−１，４−メチルテ
ン等を用いたエチレン−α−オレフィン共重合体、エチ
レン系アイオノマー、ポリアクリル酸エステルゴム、エ
チレン−α−オレフィン−ポリエン共重合体などが挙げ
られる。またスチレン−ブタジェンブロック共重合体お
よび水素化スチレン−ブタジェンブロック共重合体にお
いてはＡＢ型、ＡＢＡ型、ＡＢＡテーパー型、ラジアル
テレブロック型等を用いることができる。これらのゴム
状重合体は１種または２種以上で使用される。As the rubbery polymer, polybutadiene, styrene-
Butadiene copolymer, acrylonitrile-butadiene copolymer, styrene-butadiene block copolymer, hydrogenated styrene-butadiene block copolymer, hydrogenated styrene-butadiene random copolymer, hydrogenated acrylonitrile-butadiene copolymer Coalescence, propylene as α-olefin, butene-11 pentene-11 hexene-11
Ethylene-α-olefin copolymers using hebutene-1,4-methylpentene-1,4-methyltene, etc., ethylene ionomers, polyacrylic acid ester rubbers, ethylene-α-olefin-polyene copolymers, etc. Can be mentioned. Further, in the styrene-butadiene block copolymer and hydrogenated styrene-butadiene block copolymer, AB type, ABA type, ABA tapered type, radial teleblock type, etc. can be used. These rubbery polymers may be used alone or in combination of two or more.
耐衝撃性ポリスチレンは、ゴム質重合体の存在下にスチ
レンを主体とする芳香族ビニル化合物を重合して得られ
る。該芳香族ビニル化合物としては、スチレン、α−メ
チルスチレン、メチルスチレン、ビニルキシレン、モノ
クロルスチレン、ジクロルスチレン、モノブロムスチレ
ン、ジブロムスチレン、Ｐ−ターシャリ−ブチルスチレ
ン、エチルスチレン等が挙げられ、これらは１種または
２種以上で使用される。Impact-resistant polystyrene is obtained by polymerizing an aromatic vinyl compound mainly composed of styrene in the presence of a rubbery polymer. Examples of the aromatic vinyl compound include styrene, α-methylstyrene, methylstyrene, vinylxylene, monochlorostyrene, dichlorostyrene, monobromustyrene, dibromostyrene, P-tert-butylstyrene, ethylstyrene, etc. These may be used alone or in combination of two or more.
ＡＢＳ樹脂は、ゴム質重合体の存在下に上記したスチレ
ンを主体とする芳香族ビニル化合物と、アクリロニトリ
ルを主体とするビニルシアン化合物とを重合して得られ
る。該ビニルシアン化合物としてはアクリロニトリル、
メタクリレートリル等が挙げられる。ABS resin is obtained by polymerizing the above-mentioned aromatic vinyl compound mainly composed of styrene and a vinyl cyanide compound mainly composed of acrylonitrile in the presence of a rubbery polymer. As the vinyl cyanide compound, acrylonitrile,
Examples include methacrylate trile.
ＭＢＳ樹脂は、ゴム質重合体存在下に上記したスチレン
を主体とする芳香族ビニル化合物と、メタクリル酸メチ
ルを主体とする（メタ）アクリル酸アルキルエステルを
重合して得られる。該（メタ）アクリル酸アルキルエス
テルとしては上述したものを使用することができる。The MBS resin is obtained by polymerizing the above-mentioned aromatic vinyl compound mainly composed of styrene and a (meth)acrylic acid alkyl ester mainly composed of methyl methacrylate in the presence of a rubbery polymer. As the (meth)acrylic acid alkyl ester, those mentioned above can be used.
上記耐衝撃性ポリスチレン、ＡＢＳ樹脂またはＭＢＳ樹
脂には、芳香族ビニル化合物のほか、これらと共重合可
能な他のビニル単量体を、好ましくは３０重量％以下、
さらに好ましくは１０重量％以下の範囲で用いることも
できる。該共重合可能な他のビニル単量体としては、ア
クリル酸、メタクリル酸、マレイン酸等の不飽和酸、無
水マレイン酸、無水マレイン酸等の不飽和酸無水物、グ
リシジルメタクリレート、アリルグリシジルエーテル等
のエポキシ基含有不飽和化合物、２−ヒドロキシエチル
メタクリレート、２−ヒドロキシエチルアクリレート等
のヒドロキシル基含有不飽和化合物、ｐ−アミノスチレ
ン、アクリル酸アミノエチル等のアミノ基含有不飽和化
合物、アクリルアミド等のアミド基含有不飽和化合物、
Ｎ−フェニルマレイミド、Ｎ−シクロへキシルマレイミ
ド等のマレイミド化合物および酢酸ビニル、Ｎ−ビニル
ピロリドン等が挙げられ、これらは１種または２種以上
で使用される。The impact-resistant polystyrene, ABS resin or MBS resin contains, in addition to the aromatic vinyl compound, other vinyl monomers copolymerizable with these, preferably at most 30% by weight.
More preferably, it can be used in a range of 10% by weight or less. Examples of the other copolymerizable vinyl monomers include unsaturated acids such as acrylic acid, methacrylic acid, and maleic acid, unsaturated acid anhydrides such as maleic anhydride and maleic anhydride, glycidyl methacrylate, and allyl glycidyl ether. epoxy group-containing unsaturated compounds, hydroxyl group-containing unsaturated compounds such as 2-hydroxyethyl methacrylate and 2-hydroxyethyl acrylate, amino group-containing unsaturated compounds such as p-aminostyrene and aminoethyl acrylate, and amides such as acrylamide. group-containing unsaturated compounds,
Maleimide compounds such as N-phenylmaleimide and N-cyclohexylmaleimide, vinyl acetate, N-vinylpyrrolidone, and the like may be mentioned, and these may be used alone or in combination of two or more.
前記熱可塑性ポリエステルは、例えばジカルボン酸とジ
オール成分の縮合重合によって得られる。The thermoplastic polyester is obtained, for example, by condensation polymerization of a dicarboxylic acid and a diol component.
ジカルボン酸としては、シュウ酸、マロン酸、コハク酸
、グリタル酸、アジピン酸、スペリン酸、アゼライン酸
、セバシン酸、テレフタル酸、イソフタル酸、ｐ−カル
ボキシフェノキシ酢酸、Ｐ。Examples of dicarboxylic acids include oxalic acid, malonic acid, succinic acid, glitaric acid, adipic acid, superric acid, azelaic acid, sebacic acid, terephthalic acid, isophthalic acid, p-carboxyphenoxyacetic acid, and P.
ｐ９−ジカルボキシジフェニル、ｐ、ｐ”−ジカルボキ
シジフェニルスルホン、ｐ−カルボキシフェノキシ酢酸
、ｐ−カルボキシフェノキシプロピオン酸、Ｐ−カルボ
キシフェノキシ酪酸、Ｐ−カルボキシフェノキシ吉草酸
、ｐ−カルボキシフェノキシヘキサン酸、ｐ、ｐ’−ジ
カルボキシジフェニルメタン、ｐ、ｐ’−ジカルボキシ
ジフェニルプロパン、ｐ、ｐ’−ジカルボキシジフェニ
ルオクタン、３−アルキル−４−（β−カルボキシエト
キシ）安息香酸、２，６−ナフタレンジカルボン酸、２
．７−ナフタレンジカルボン酸、これらの誘導体などが
用いられる。これらは１種または２種以上混合して使用
され、テレフタル酸、テレフタル酸とイソフタル酸の混
合物が特に好ましい。p9-dicarboxydiphenyl, p, p”-dicarboxydiphenyl sulfone, p-carboxyphenoxyacetic acid, p-carboxyphenoxypropionic acid, P-carboxyphenoxybutyric acid, P-carboxyphenoxyvaleric acid, p-carboxyphenoxyhexanoic acid, p , p'-dicarboxydiphenylmethane, p,p'-dicarboxydiphenylpropane, p,p'-dicarboxydiphenyl octane, 3-alkyl-4-(β-carboxyethoxy)benzoic acid, 2,6-naphthalene dicarboxylic acid ,2
．． 7-naphthalene dicarboxylic acid, derivatives thereof, etc. are used. These may be used singly or in combination, and terephthalic acid and a mixture of terephthalic acid and isophthalic acid are particularly preferred.
ジオール成分としては、脂肪族ジオールまたは芳香族ジ
オールが用いられる。脂肪族ジオールとしては、例えば
エチレングリコール、１，３−プロピレングリコール、
１．４−テトラメチレングリコール、１，６−ヘキジレ
ングリコール、１゜１０−デカメチレングリコール、１
，１２−ドデカメチレングリコールなどの炭素数２〜１
２の直鎖アルキレングリコールが挙げられる。芳香族ジ
オールとしては、ビスフェノールＡ、ｐ−キシレングリ
コール、ピロカテコール、レゾルシノール、ヒドロキノ
ン、これらの化合物のアルキル置換誘導体およびこれら
の誘導体などが挙げられる。これらは１種または２種以
上で使用される。As the diol component, aliphatic diols or aromatic diols are used. Examples of aliphatic diols include ethylene glycol, 1,3-propylene glycol,
1.4-tetramethylene glycol, 1,6-hexylene glycol, 1゜10-decamethylene glycol, 1
, 12-dodecamethylene glycol, etc. having 2 to 1 carbon atoms
2 linear alkylene glycols are mentioned. Examples of aromatic diols include bisphenol A, p-xylene glycol, pyrocatechol, resorcinol, hydroquinone, alkyl-substituted derivatives of these compounds, and derivatives thereof. These may be used alone or in combination of two or more.
また熱可塑性ポリエステルとしては、Ｐ−ヒドロキシ安
息香酸およびその誘導体から得られるポリエステルと、
上記ジカルボン酸および／またはジオール成分とを共重
合して得られるもの、さらに公知のポリエステルエラス
トマーを用いることもできる。In addition, as thermoplastic polyesters, polyesters obtained from P-hydroxybenzoic acid and its derivatives,
Those obtained by copolymerizing the above dicarboxylic acid and/or diol components, and further known polyester elastomers can also be used.
好ましい熱可塑性ポリエステルとして、ポリエチレンテ
レフタレート、ポリブチレンテレフタレート、テレフタ
ル酸および／またはイソフタル酸とビスフェノールＡか
らなるポリエステル、ｐ−ヒドロキシ安息香酸残基を有
するポリエステルなどが挙げられ、ポリエチレンテレフ
タレートおよびポリブチレンテレフタレートは耐衝撃性
の改良効果が大きく特に好ましい。Preferred thermoplastic polyesters include polyethylene terephthalate, polybutylene terephthalate, polyesters made of terephthalic acid and/or isophthalic acid and bisphenol A, and polyesters having p-hydroxybenzoic acid residues. It is particularly preferred since it has a large effect of improving impact resistance.
前記ポリアミドは、芳香族および／または脂肪族のアミ
ド基を有する繰返しユニットを構成成分として含む縮合
生成物であり、例えば、アミノ基とカルボン酸基との間
に少なくとも２個の炭素原子を有するモノアミノ−モノ
カルボン酸またはそのラクタムを重合する方法、１つの
アミノ基の間に少なくとも２個の炭素原子を有するジア
ミンとジカルボン酸またはその誘導体とを実質的に等モ
ル量で縮合重合させる方法、上記モノアミノ−モノカル
ボン酸またはそのラクタムを実質的に等モル量のジアミ
ンおよびジカルボン酸とともに縮合重合させる方法など
により得られる。The polyamide is a condensation product containing as a constituent a repeating unit having aromatic and/or aliphatic amide groups, for example, a monoamino compound having at least 2 carbon atoms between an amino group and a carboxylic acid group. - A method of polymerizing a monocarboxylic acid or a lactam thereof, a method of condensation polymerization of a diamine having at least two carbon atoms between one amino group and a dicarboxylic acid or a derivative thereof in substantially equimolar amounts, the monoamino - Obtained by condensation polymerization of monocarboxylic acid or its lactam together with substantially equimolar amounts of diamine and dicarboxylic acid.
モノアミノ−モノカルボン酸またはそのラクタムとして
は、例えばε−アミノカルボン酸、ブチロラクタム、ビ
バロラクタム、カプロラクタム、カプリルラクタム、エ
ナントラクタム、ウンデカノラクタム、ドデカノラクタ
ム、３−および４アミノ安患香酸などが挙げられる。Examples of monoamino-monocarboxylic acids or lactams thereof include ε-aminocarboxylic acid, butyrolactam, bivalolactam, caprolactam, capryllactam, enantholactam, undecanolactam, dodecanolactam, 3- and 4-aminobenzoic acid, and the like. It will be done.
ジアミンとしては、例えばトリメチレンジアミン、テト
ラメチレンジアミン、ペンタメチレンジアミン、ヘキサ
メチレンジアミン、オクタメチレンジアミン、デカメチ
レンジアミン、ドデカメチレンジアミン、ヘキサデカメ
チレンジアミン等の一般式Ｈ２Ｎ （ＣＨｚ）、ＮＨ２
（式中のｎは２〜１６の整数）で表されるジアミン；例
えば２．２＝ジメチルペンタメチレンジアミン、２，２
．４−トリメチルへキサメチレンジアミン、２．４４−
トリメチルへキサメチレンジアミン等のアルキル化ジア
ミン；例えばＰ−フェニレンジアミン、４．４′−ジア
ミノジフェニルスルホン、４．４１−ジアミノジフェニ
ルエーテル、ｍ−フェニレンジアミン、４，４′−ジア
ミノジフェニルメタン等の芳香族ジアミン；例えばジア
ミノジシクロヘキシルメタン等の脂環式ジアミンなどが
挙げられる。これらは１種または２種以上混合して用い
られる。Examples of diamines include those with the general formula H2N (CHz), NH2, such as trimethylenediamine, tetramethylenediamine, pentamethylenediamine, hexamethylenediamine, octamethylenediamine, decamethylenediamine, dodecamethylenediamine, and hexadecamethylenediamine.
(in the formula, n is an integer of 2 to 16); for example, 2.2=dimethylpentamethylenediamine, 2,2
．． 4-trimethylhexamethylenediamine, 2.44-
Alkylated diamines such as trimethylhexamethylene diamine; aromatic diamines such as P-phenylene diamine, 4,4'-diaminodiphenyl sulfone, 4,41-diaminodiphenyl ether, m-phenylene diamine, 4,4'-diaminodiphenylmethane, etc. ; Examples include alicyclic diamines such as diaminodicyclohexylmethane. These may be used alone or in combination of two or more.
ジカルボン酸としては、芳香族ジカルボン酸および／ま
たは脂肪族ジカルボン酸が用いられる。As the dicarboxylic acid, aromatic dicarboxylic acids and/or aliphatic dicarboxylic acids are used.
芳香族ジカルボン酸としては、イソフタル酸、テレフタ
ル酸等が挙げられ、脂肪族ジカルボン酸としては、シュ
ウ酸の他、例えばセバシン酸、オクタデカンジオイック
酸、グルタル酸、ピメリン酸、アジピン酸等の一般式Ｈ
００Ｃ−Ｒ−Ｃ００Ｈ（式中、Ｒは少なくとも２個の炭
素原子を有する２価の脂肪族基）で表されるジカルボン
酸が挙げられる。これらの各種化合物は１種または２種
以上で使用することができる。Examples of aromatic dicarboxylic acids include isophthalic acid and terephthalic acid, and examples of aliphatic dicarboxylic acids include oxalic acid and general formulas such as sebacic acid, octadecanedioic acid, glutaric acid, pimelic acid, and adipic acid. H
Examples include dicarboxylic acids represented by 00C-R-C00H (wherein R is a divalent aliphatic group having at least 2 carbon atoms). These various compounds can be used alone or in combination of two or more.
またポリアミドとして、ポリエステルアミドエラストマ
ー、ポリエーテルエステルアミドエラストマー、ポリエ
ーテルアミドエラストマーなどの公知のポリアミドエラ
ストマーも使用できる。好ましいポリアミドとして、ナ
イロン６、ナイロン６６、ナイロン４６、ナイロン１２
、ナイロンＭＸＤ６ （ポリメタキシリレンアジパミド
）などが挙げられる。Furthermore, known polyamide elastomers such as polyesteramide elastomer, polyetheresteramide elastomer, and polyetheramide elastomer can also be used as the polyamide. Preferred polyamides include nylon 6, nylon 66, nylon 46, and nylon 12.
, nylon MXD6 (polymethaxylylene adipamide), and the like.
前記ポリアリールエーテルとしては、
一般式（１） −（−０−Ｒ−０−Ｒ’→−から選
ばれた二価のフェノールの残基であり、Ｒ゛は、上記式
（Ｉｆ）および
（式中、Ｚは酸素、硫黄または４．４゛−ビスフェノー
ルなどの芳香族ジオール残基を示す）で表される構造を
有する。この繰返し単位の具体例としては、
から選ばれたジプロモヘンゼノイド化合物残基またはシ
ョートベンゼノイド化合物残基であり、ＱおよびＱｌは
、−〇−１−Ｓ−−ＳＯ□−またはこれらの基を含む炭
素数１〜１８の２価の炭化水素残基（ただし、Ｑが一〇
−のとき、Ｑｏは一〇−以外のものであり、Ｑ“が−〇
−のときＱは、〇−以外のものであり、またＲが式（Ｉ
ｔ）のとき、Ｒ゛は式（ＩＶ）であり、Ｒ“が式（ＩＩ
）のとき、Ｒは式（ＩＮ）である）を意味する〕で表さ
れる化合物が用いられる。The polyarylether is a residue of a dihydric phenol selected from the general formula (1) -(-0-R-0-R'→-, and R' is the residue of the above formula (If) and ( In the formula, Z represents oxygen, sulfur, or an aromatic diol residue such as 4.4-bisphenol.Specific examples of this repeating unit include dipromohenze selected from is a noid compound residue or a short benzenoid compound residue, and Q and Ql are -〇-1-S--SO□- or a divalent hydrocarbon residue having 1 to 18 carbon atoms containing these groups ( However, when Q is 10-, Qo is other than 10-, and when Q" is -0-, Q is other than 0-, and R is of the formula (I
t), R'' is the formula (IV), and R'' is the formula (II
), R is the formula (IN)] is used.
前記ポリスルホンは、繰返し単位中に、Ｈ３
これらの繰返し単位を種々の割合で有するものなどが挙
げられる。好ましいポリスルポンとしてはＣＨ３
が挙げられる。Examples of the polysulfone include those having H3 repeating units in various proportions in the repeating unit. A preferred polysulfone is CH3.
前記ポリカーボネートとしては、
一般式（ＶＩ）
一般式（■）−〇
（−Ａ ｒ−０−Ｃ−０→Ｔ
（式中、Ａｒはフェニレン基、またはアルキル基、アル
コキシ基、ハロゲン原子もしくはニトロ基によって置換
されたフェニレン基、Ａは炭素−炭素結合、アルキリデ
ン基、シクロアルキリデン基、アルキレン基、シクロア
ルキレン基、アゾイミノ基、硫黄原子、酸素原子または
スルホキシド基、ｎは少なくとも２の整数を示す）で表
されるものが用いられる。好ましいポリカーボネートと
して、一般式（■）または（■）中のＡｒがＰ−フェニ
レン基、Ａがイソプロピリデン基を有するものが挙げら
れる。The polycarbonate has general formula (VI) general formula (■)-〇(-A r-0-C-0→T (wherein, Ar is a phenylene group, or an alkyl group, an alkoxy group, a halogen atom, or a nitro group). A is a carbon-carbon bond, an alkylidene group, a cycloalkylidene group, an alkylene group, a cycloalkylene group, an azoimino group, a sulfur atom, an oxygen atom or a sulfoxide group, and n is an integer of at least 2. Preferred polycarbonates include those in which Ar in formula (■) or (■) has a P-phenylene group and A has an isopropylidene group.
前記ポリアセタールは、ホルムアルデヒドまたはトリオ
キサンの重合によって得られる重合体である。ホルムア
ルデヒドから製造されるポリアセタールは、式−＋ Ｃ
Ｈ２−０ｈ−で表される構造を有し、通常、熱および化
学的抵抗性を増加させるため、末端基をエステルまたは
エーテルに変換される。またポリアセタール共重合体も
含まれ、これらの共重合体にはホルムアルデヒドに活性
水素を提供することのできる他の物質の単量体またはプ
レポリマー、例えばアルキレングリコール、ポリチオー
ル、ビニルアセテート−アクリル酸共重合体、ブタジェ
ン／アクリロニトリルポリマーまたはその誘導体とのブ
ロック共重合体が含まれる。トリオキサンの重合で得ら
れるポリアセタールは、通常、共重合可能な他の化合物
と共重合される。該共重合可能な化合物としては、例え
ばアルデヒド、環状エーテル、ビニル化合物、ケトン環
状カーボネート、エポキシド、イソシアネート、エーテ
ルなどが挙げられ、これらの化合物にはエチレンオキシ
ド、１．３−ジオキソラン、１３ジオキサン、エピクロ
ルヒドリン、プロピレンオキシド、イソブチレンオキシ
ド、スチレンオキシドなどが含まれる。The polyacetal is a polymer obtained by polymerizing formaldehyde or trioxane. Polyacetals made from formaldehyde have the formula −+C
It has the structure H2-0h-, and the end groups are usually converted to esters or ethers to increase thermal and chemical resistance. Also included are polyacetal copolymers, which include monomers or prepolymers of other substances capable of providing active hydrogen to formaldehyde, such as alkylene glycols, polythiols, vinyl acetate-acrylic acid copolymers, etc. block copolymers with butadiene/acrylonitrile polymers or derivatives thereof. The polyacetal obtained by polymerizing trioxane is usually copolymerized with other copolymerizable compounds. Examples of the copolymerizable compound include aldehydes, cyclic ethers, vinyl compounds, ketone cyclic carbonates, epoxides, isocyanates, and ethers, and these compounds include ethylene oxide, 1,3-dioxolane, 13-dioxane, epichlorohydrin, Includes propylene oxide, isobutylene oxide, styrene oxide, etc.
前記熱可塑性イソシアネート樹脂としては、例えば、ト
ルエンジイソシアネート（ＴＤＩ）、ジフェニルメタン
−４，４−ジイソシアネート（ＭＤＩ）、広範囲のポリ
オール、例えばポリオキシエチレングリコール、ポリオ
キシプロピレングリコール、ヒドロキシ末端ポリエステ
ル、オキシエチレン−オキシプロピレングリコール等か
ら製造したポリウレタンが用いられる。これらの熱可塑
性ポリウレタンは通常１２０°Ｃ以上、好ましくは１５
０〜２００°Ｃの結晶性融点を有するものが用いられる
。The thermoplastic isocyanate resins include, for example, toluene diisocyanate (TDI), diphenylmethane-4,4-diisocyanate (MDI), a wide range of polyols such as polyoxyethylene glycol, polyoxypropylene glycol, hydroxy-terminated polyesters, oxyethylene-oxy Polyurethane made from propylene glycol or the like is used. These thermoplastic polyurethanes usually have a temperature of 120°C or higher, preferably 15°C or higher.
Those having a crystalline melting point of 0 to 200°C are used.
前記ポリフェニレンエーテルは、
（式中、Ｒ＋ 、Ｒｚ 、Ｒ：＋およびＲ１は同一また
は異なるアルキル基、アリール基、ハロゲン原子、水素
原子などの残基を示し、ｎは重合度を示す）で表される
繰返し構造単位からなる重合体である。The polyphenylene ether is represented by (wherein R+, Rz, R:+ and R1 are the same or different alkyl groups, aryl groups, halogen atoms, hydrogen atoms, etc., and n indicates the degree of polymerization). It is a polymer consisting of repeating structural units.
この具体例としては、ポリ（２，６−シメチルフエニレ
ンー１．４−エーテル）、ポリ（２，６ジエチルフエニ
レンー１．４−エーテル）、ポリ（２，６−ジプロムフ
エニレンー１，４−エーテル）、ポリ（２−メチル−６
−ニチルフエニレン１．４−エーテル）、ポリ（２−ク
ロル−６メチルフエニレンー１，４−エーテル）、ポリ
（２−メチル−６−イツプロビルフエニレンー１゜４−
エーテル）、ポリ（２，６−ジーｎ−プロピルフェニレ
ン−１，４−エーテル）、ポリ（２−クロルー６−プロ
ムフェニレン−１，４−エーテル）、ポリ（２−クロル
−６−ニチルフエニレン１．４−エーテル）、ポリ（２
−メチルフェニレン−１，４−エーテル）、ポリ（２−
クロルフェニレン−１，４−エーテル）、ポリ（２−フ
ェニルフェニレン−１，４−エーテル）、ポリ（２メチ
ル−６−フェニルフェニレン−１，４−エーテル）、ポ
リ（２−ブロム−６−フェニルフェニレン−１，４−エ
ーテル）、ポリ（２，４’メチルフェニルフェニレン−
１，４−エーテル）、ポリ（２，３，６−）ツメチルフ
ェニレン−１４−エーテル）およびこれらの共重合体な
どが挙げられる。これらのうち２．６−シメチルフエノ
ールから得られる重合体および２．６−シメチルフエノ
ールと２．３．６−トリメチルフエノールから得られる
共重合体が特に好ましい。Specific examples include poly(2,6-dimethylphenylene-1,4-ether), poly(2,6-diethylphenylene-1,4-ether), and poly(2,6-diprophenylene). -1,4-ether), poly(2-methyl-6
-Nitylphenylene 1,4-ether), Poly(2-chloro-6methylphenylene-1,4-ether), Poly(2-methyl-6-itsuprobylphenylene-1゜4-
ether), poly(2,6-di-n-propylphenylene-1,4-ether), poly(2-chloro-6-propylphenylene-1,4-ether), poly(2-chloro-6-nitylphenylene 1. 4-ether), poly(2
-methylphenylene-1,4-ether), poly(2-
chlorophenylene-1,4-ether), poly(2-phenylphenylene-1,4-ether), poly(2-methyl-6-phenylphenylene-1,4-ether), poly(2-bromo-6-phenyl) phenylene-1,4-ether), poly(2,4'methylphenylphenylene-
1,4-ether), poly(2,3,6-)methylphenylene-14-ether), and copolymers thereof. Among these, particularly preferred are polymers obtained from 2,6-dimethylphenol and copolymers obtained from 2,6-dimethylphenol and 2,3,6-trimethylphenol.
熱可塑性樹脂は１種単独でまたは２種以上混合して用い
られるが、好ましい組合わせとして、ポＩＪ フェニレ
ンエーテルとスチレン系樹ＪＩＬホ’Ｊフェニレンエー
テルとポリエチレンおよび／またはポリプロピレン、′
ポリフェニレンエーテルとポリアミド、ポリフェニレン
エーテルと熱可塑性ポリエステル、ポリアミドとポリエ
チレンおよび／またはポリプロピレン、熱可塑性ポリエ
ステルとポリエチレンおよび／またはポリプロピレン、
ポリフェニレンスルフィドとＡＢｓ樹脂、ポリスルホン
とＡＢＳ樹脂、ポリアセタールと熱可塑性イソシアネー
ト樹脂、ポリカーボネートとＡＢＳ樹脂等が挙げられる
。Thermoplastic resins can be used singly or in a mixture of two or more, but preferred combinations include polyphenylene ether, styrene resin, phenylene ether, polyethylene and/or polypropylene,
polyphenylene ether and polyamide, polyphenylene ether and thermoplastic polyester, polyamide and polyethylene and/or polypropylene, thermoplastic polyester and polyethylene and/or polypropylene,
Examples include polyphenylene sulfide and ABs resin, polysulfone and ABS resin, polyacetal and thermoplastic isocyanate resin, polycarbonate and ABS resin, and the like.
本発明の熱可塑性樹脂組成物には、必要に応じてゴム状
重合体として高分子エチレン−α−オレフィン共重合体
を０〜８０重量部、好ましくは０〜６０重量部の範囲で
含有することができる。該ゴム質重合体としては、前述
したゴム質重合体の他、エチレンとエポキシ基含有不飽
和化合物の共重合体、該共重合体にラジカル重合可能な
ビニル単量体から得られる重合体をグラフト反応したも
の、エチレンと不飽和酸の共重合体等を用いることがで
きる。熱可塑性樹脂とゴム質重合体との相溶性が悪い場
合には公知の相溶化方法により配合することができる。The thermoplastic resin composition of the present invention may contain a high molecular weight ethylene-α-olefin copolymer as a rubbery polymer in an amount of 0 to 80 parts by weight, preferably 0 to 60 parts by weight, if necessary. I can do it. In addition to the above-mentioned rubbery polymer, the rubbery polymer includes a copolymer of ethylene and an unsaturated compound containing an epoxy group, and a polymer obtained from a radically polymerizable vinyl monomer grafted onto the copolymer. A reacted product, a copolymer of ethylene and an unsaturated acid, etc. can be used. If the thermoplastic resin and the rubbery polymer have poor compatibility, they can be blended by a known compatibilization method.
例えば、ポリアミドとゴムの配合には、（１）相溶化剤
として無水マレイン酸変性のエチレン−αオレフィン共
重合体を用いる方法、（２）カルボキシル基含有エチレ
ン重合体を用いる方法、（３）エチレン−グリシジルメ
タクリレート−（酢酸ビニル）共重合体を用いる方法な
どが採用される。熱可塑性ポリエステルとゴムの配合に
は、上記（１）または（３）の方法の他、（４）エチレ
ン−グリシジルメタクリレート共重合体にポリメタクリ
ル酸メチル、ポリスチレン、アクリロニトリル−スチレ
ン共重合体等がグラフトしたものを用いる方法などが採
用される。ポリアミドとＡＢＳ樹脂の配合には、（５）
カルボキシル基で変性したＡＳ樹脂またはカルボキシル
基で変性したＡＢＳ樹脂を用いる方法などが採用される
。ポリフェニレンエーテル、ポリアミドまたは熱可塑性
ポリエステルとゴム質重合体の配合には、（６）混練時
に酸無水物基、カルボキシル基、アミノ基、ヒドロキシ
ル基、エポキシ基含有不飽和化合物または過酸化物を添
加する方法、（７）酸無水物で変性されたゴム質重合体
と特定の官能基で変性されたスチレン系樹脂を使用する
方法、（８）無水マレイン酸で変性されたポリフェニレ
ンエーテルを使用する方法などが採用される。For example, when blending polyamide and rubber, (1) a method using an ethylene-α olefin copolymer modified with maleic anhydride as a compatibilizer, (2) a method using a carboxyl group-containing ethylene polymer, (3) a method using ethylene A method using a -glycidyl methacrylate-(vinyl acetate) copolymer is adopted. In addition to the method (1) or (3) above, the thermoplastic polyester and rubber can be blended by (4) ethylene-glycidyl methacrylate copolymer grafted with polymethyl methacrylate, polystyrene, acrylonitrile-styrene copolymer, etc. Methods such as using a For blending polyamide and ABS resin, (5)
A method using an AS resin modified with a carboxyl group or an ABS resin modified with a carboxyl group is adopted. When blending polyphenylene ether, polyamide, or thermoplastic polyester with a rubbery polymer, (6) adding an unsaturated compound or peroxide containing an acid anhydride group, carboxyl group, amino group, hydroxyl group, or epoxy group during kneading. (7) A method using a rubbery polymer modified with an acid anhydride and a styrene resin modified with a specific functional group, (8) A method using a polyphenylene ether modified with maleic anhydride, etc. will be adopted.
本発明の熱可塑性樹脂組成物には、必要に応じて各種架
橋剤、充填剤、耐熱安定剤、老化防止側、架橋促進剤な
どを配合して用いることができる。The thermoplastic resin composition of the present invention may contain various crosslinking agents, fillers, heat stabilizers, anti-aging agents, crosslinking accelerators, and the like, if necessary.
この熱可塑性樹脂組成物は、前述したエポキシ化低分子
量共重合体を含むため、耐衝撃性、成形加工性および成
形品表面性に優れる。Since this thermoplastic resin composition contains the above-mentioned epoxidized low molecular weight copolymer, it has excellent impact resistance, moldability, and surface properties of molded products.
［実施例］
以下、本発明を実施例により詳しく説明するが、本発明
はこれらの実施例に限定されるものではない。[Examples] Hereinafter, the present invention will be explained in detail with reference to Examples, but the present invention is not limited to these Examples.
実施例中の各種測定は下記の方法に従った。Various measurements in the examples were carried out according to the following methods.
（１）エポキシ基含量
１〜２ｇのエポキシ化低分子量エチレン−αオレフィン
共重合体を１００ｍｊ！のクロロホルムに溶解させ、テ
トラメチルアンモニウムブロマイドを触媒として０．Ｉ
ＮのＨＣｆＯ４を用いた滴定により定量した。(1) 100 mj of epoxidized low molecular weight ethylene-α olefin copolymer with an epoxy group content of 1 to 2 g! of chloroform and using tetramethylammonium bromide as a catalyst. I
It was determined by titration of N with HCfO4.
（２）低分子量エチレン−α−オレフィン共重合体の分
子量
トリクロロベンゼンを溶媒としてＧＰＣにより測定した
。(2) Molecular weight of low molecular weight ethylene-α-olefin copolymer Measured by GPC using trichlorobenzene as a solvent.
（３）プロピレン含量 赤外吸収スペクトルにより測定した。(3) Propylene content Measured by infrared absorption spectrum.
（４）アイゾツト衝撃強度
ＡＳＴＭ Ｄ ２５６に従い、厚み１／８″ノツチ
付で２３°Ｃおよび一３０°Ｃで測定した。(4) Izot impact strength Measured according to ASTM D 256 with a 1/8" thick notch at 23°C and -30°C.
（５）流動性
ＪＩＳ Ｋ ７２１０に準じて２６０°Ｃ１荷重１
０ｋｇでＭＦＲ（メルトフローレート）を測定した。(5) Fluidity 260°C 1 load 1 according to JIS K 7210
MFR (melt flow rate) was measured at 0 kg.
（６）引張破断強度、伸びおよび永久伸びＪＩＳ Ｋ
６３０１に従って測定した。(6) Tensile breaking strength, elongation and permanent elongation JIS K
Measured according to 6301.
実施例１
３！のフラスコに、Ｍｗｌｏ、０００、プロピレン含量
３５モル％およびヨウ素価３０の低分子量エチレン−プ
ロピレン−非共役ジエン共重合体（以下、「低分子量Ｅ
ＰＤＭ、という、非共役ジエン：ジシクロペンタジェン
）４５０ｇが溶解されたトルエン溶液２０００ｍｆを導
入した。この溶液に蟻酸１モル、および過酸化水素２モ
ルを３０重量％過酸化水素水として加え、激しく撹拌し
ながら加温した。温度を３５〜４０°Ｃに保って７時間
撹拌を続けた後、撹拌を停止し、分離した水層を除いた
。ポリマー溶液を水によって数回洗浄した後、大量のメ
タノール中に注いでエポキシ化低分子量ＥＰＤＭを得た
。このエポキシ化低分子量ＥＰＤＭを、減圧下で乾燥し
た後、エポキシ基の含量を測定した。エポキシ基含量は
５３ミリモル／１００ｇであり、低分子量ＥＰＤＭ中の
二重結合の４５％がエポキシ化されたことが判明した。Example 1 3! A low molecular weight ethylene-propylene-nonconjugated diene copolymer (hereinafter referred to as “low molecular weight E
2000 mf of a toluene solution in which 450 g of PDM (non-conjugated diene: dicyclopentadiene) was dissolved was introduced. To this solution, 1 mole of formic acid and 2 moles of hydrogen peroxide were added as a 30% by weight hydrogen peroxide solution, and the mixture was heated with vigorous stirring. After stirring was continued for 7 hours while maintaining the temperature at 35-40°C, stirring was stopped and the separated aqueous layer was removed. The polymer solution was washed several times with water and then poured into a large amount of methanol to obtain epoxidized low molecular weight EPDM. After drying this epoxidized low molecular weight EPDM under reduced pressure, the content of epoxy groups was measured. The epoxy group content was found to be 53 mmol/100 g, indicating that 45% of the double bonds in the low molecular weight EPDM were epoxidized.
このエポキシ化低分子量ＥＰＤＭの赤外吸収スペクトル
を第１図に示した。The infrared absorption spectrum of this epoxidized low molecular weight EPDM is shown in FIG.
実施例２
実施例１において、Ｍｗｌｌ、０００、プロピレン含量
４０モル％およびヨウ素価１９の低分子量ＥＰＤＭを使
用する以外は、実施例１と同様の操作を行い、エポキシ
化低分子量ＥＰＤＭを得た。Example 2 An epoxidized low molecular weight EPDM was obtained in the same manner as in Example 1, except that low molecular weight EPDM with Mwll, 000, propylene content of 40 mol %, and iodine value of 19 was used.
該ＥＰＤＭのエポキシ基含量は３１ミリモル／１００ｇ
であり、低分子量ＥＰＤＭ中の二重結合中の４１％がエ
ポキシ化されたことが判明した。The epoxy group content of the EPDM is 31 mmol/100g
It was found that 41% of the double bonds in the low molecular weight EPDM were epoxidized.
実施例３
実施例１において、蟻酸の代わりに安息香酸を用いた以
外は実施例１と同様の操作を行い、エポキシ化低分子量
ＥＰＤＭを得た。該ＥＰＤＭのエポキシ基含量は１６ミ
リモル／１００ｇであり、低分子量ＥＰＤＭ中の二重結
合中の１４％がエポキシ化されたことが判明した。Example 3 An epoxidized low molecular weight EPDM was obtained by carrying out the same operation as in Example 1 except that benzoic acid was used instead of formic acid. The epoxy group content of the EPDM was 16 mmol/100 g, indicating that 14% of the double bonds in the low molecular weight EPDM were epoxidized.
実施例４
実施例１において、溶媒としてトルエンの代わりに塩化
メチレンを用いた以外は実施例１と同様の操作を行い、
エポキシ化低分子量ＥＰＤＭを得た。該ＥＰＤＭのエポ
キシ基含量は４０ミリモル／１００ ｇであり、低分子
量ＥＰＤＭ中の二重結合の３４％がエポキシ化されたこ
とが判明した。Example 4 The same operation as in Example 1 was performed except that methylene chloride was used instead of toluene as the solvent.
Epoxidized low molecular weight EPDM was obtained. The epoxy group content of the EPDM was found to be 40 mmol/100 g, and 34% of the double bonds in the low molecular weight EPDM were epoxidized.
実施例５〜６および比較例１．２
下記に示す（ａ）〜（ｇ）の配合物を第１表に示す配合
量で配合し、溶融混練して熱可塑性樹脂組成物を゛調製
した。この際、エポキシ化低分子量ＥＰＤＭまたは未変
性低分子量ＥＰＤＭは、ポンプを用いて押出し機途中か
ら添加した。得られたペレット状組成物を除湿乾燥機で
充分乾燥し、射出成形機で評価試片を成形した。該試験
片の物性について評価し、結果を第１表に示した。Examples 5 to 6 and Comparative Example 1.2 The following blends (a) to (g) were blended in the amounts shown in Table 1 and melt-kneaded to prepare thermoplastic resin compositions. At this time, the epoxidized low molecular weight EPDM or unmodified low molecular weight EPDM was added midway through the extruder using a pump. The obtained pellet-like composition was sufficiently dried in a dehumidifying dryer, and an evaluation sample was molded in an injection molding machine. The physical properties of the test piece were evaluated and the results are shown in Table 1.
（ａ）ポリブチレンテレフタレート（ポリプラスチック
社製商品名シュラネックスＸＤ５１８）（ｂ）ナイロン
６（東し社製商品名アミランＣＭ（Ｃ）エチレン−グリ
シジルメタクリレート共重合体グラフ）ＰＭＭＡ（日本
油脂社製商品名モディパーＦ Ａ４２００）
（ｄ）ポリカーボネート（井光社製商品名Ａ２２（ｅ）
エチレン−プロピレン共重合体（日本合成ゴム社製 Ｅ
Ｐ−０１Ｐ）
（ｆ）実施例１で得たエポキシ化低分子量ＥＰＤＭ（ｇ
）実施例１で用いた低分子量ＥＰＤＭ以下余白
第１表の結果から、比較例に比べ、実施例５〜９ではア
イゾツト衝撃強度に優れ、また実施例５．６および９で
は流動性にも優れることが示される。(a) Polybutylene terephthalate (Product name: Shuranex XD518, manufactured by Polyplastics Co., Ltd.) (b) Nylon 6 (Product name: Amilan CM, manufactured by Toshi Co., Ltd. (C) Ethylene-glycidyl methacrylate copolymer graph) PMMA (Product name, manufactured by NOF Corporation) (Modiper F A4200) (d) Polycarbonate (Ikosha product name A22 (e)
Ethylene-propylene copolymer (manufactured by Japan Synthetic Rubber Co., Ltd. E
P-01P) (f) Epoxidized low molecular weight EPDM obtained in Example 1 (g
) Below the low molecular weight EPDM used in Example 1 From the results in Table 1, Examples 5 to 9 are superior in Izot impact strength, and Examples 5.6 and 9 are superior in fluidity, compared to Comparative Examples. It is shown that
実施例１Ｏ〜１１および比較例３
ゴム質重合体としてエチレン−プロピレン−非共役ジエ
ン共重合体（ＥＰＤＭ、日本合成ゴム社製）および水添
スチレン−ブタジェン−スチレントリブロック共重合体
（ＳＥＢＳ、シェル社製商品名クレイトンＧ１６５０）
を、それぞれアクリロニトリル−スチレン共重合体（Ａ
Ｓ共重合体、（ｊ））にグラフト重合し、グラフト共重
合体（ｈ）および（ｉ）を得た。その共重合体の成分を
第２表に示した。Examples 1O to 11 and Comparative Example 3 As rubbery polymers, ethylene-propylene-nonconjugated diene copolymer (EPDM, manufactured by Japan Synthetic Rubber Co., Ltd.) and hydrogenated styrene-butadiene-styrene triblock copolymer (SEBS, shell (Product name: Clayton G1650)
and acrylonitrile-styrene copolymer (A
Graft copolymerization was performed on S copolymer (j)) to obtain graft copolymers (h) and (i). The components of the copolymer are shown in Table 2.
第 ２ 表
このグラフト共重合体を用いてスチレン系熱可塑性樹脂
組成物を第３表に示す配合で調製し、実施例１と同様に
して評価試験片を成形してその評価を行い、結果を第３
表に示した。Table 2 Using this graft copolymer, a styrenic thermoplastic resin composition was prepared according to the formulation shown in Table 3, and evaluation test pieces were molded and evaluated in the same manner as in Example 1. Third
Shown in the table.
第 ３ 表
イジツト衝撃強度および流動性ともに優れることが示さ
れる。Table 3 shows that both the impact strength and fluidity are excellent.
実施例１２および比較例４
ポリブチレンテレフタレート１００重量部にエポキシ化
低分子量ＥＰＤＭを６６．６重量部加え、さらに架橋剤
として硫黄１．１７重置部および架橋助剤２．３３重量
部を配合してニーダ−で溶融混練りし、プレス成形した
。その後、ＪＩＳ ３号ダンベルを打ち抜き、引張破
壊特性を測定し、結果を第４表に示した。Example 12 and Comparative Example 4 66.6 parts by weight of epoxidized low molecular weight EPDM was added to 100 parts by weight of polybutylene terephthalate, and 1.17 parts by weight of sulfur as a crosslinking agent and 2.33 parts by weight of a crosslinking aid were added. The mixture was melt-kneaded in a kneader and press-molded. Thereafter, JIS No. 3 dumbbells were punched out and their tensile fracture properties were measured, and the results are shown in Table 4.
以下余白
第３表の結果から、ゴム変性したスチレン系熱可塑性樹
脂とエポキシ化低分子量共重合体の組成物である実施例
１０．１１は、比較例に比べ、ア第
表
＊１：伸びないため測定不可能
第４表の結果から、本実施例では、未変性の低分子ＥＰ
ＤＭを用いた比較例に較べ、破壊強度、破断伸びおよび
永久伸びの全てが改良されることが示される。From the results in Table 3 in the margin below, it can be seen that Example 10.11, which is a composition of rubber-modified styrenic thermoplastic resin and epoxidized low molecular weight copolymer, does not stretch as compared to the comparative example in Table A *1. From the results in Table 4, in this example, unmodified low-molecular EP
It is shown that the breaking strength, elongation at break, and permanent elongation are all improved compared to the comparative example using DM.
（発明の効果〕
本発明のエポキシ化低分子量エチレン−α−オレフィン
共重合体は、分散性に優れ、各種ゴム状または樹脂状重
合体の改質剤、改質助剤、潤滑油添加剤、水性分散剤の
分散助剤、塗料およびその改質剤、接着剤、シーラント
およびその改質剤、ルーフィング剤およびその改質剤等
として優れた性能を発揮することができる。(Effects of the Invention) The epoxidized low molecular weight ethylene-α-olefin copolymer of the present invention has excellent dispersibility, and can be used as a modifier for various rubber-like or resinous polymers, a modification aid, a lubricating oil additive, It can exhibit excellent performance as a dispersion aid for aqueous dispersants, paints and their modifiers, adhesives, sealants and their modifiers, roofing agents and their modifiers, etc.
また本発明の熱可望性樹脂組成物は、上記エポキシ化低
分子量共重合体を含むため、耐衝撃性、成形加工性およ
び成形品表面性に優れる。Furthermore, since the thermoplastic resin composition of the present invention contains the above-mentioned epoxidized low molecular weight copolymer, it has excellent impact resistance, molding processability, and surface properties of molded products.
第１図は、実施例１で得られたエポキシ化低分子量共重
合体の赤外吸収スペクトルを示す図である。FIG. 1 is a diagram showing an infrared absorption spectrum of the epoxidized low molecular weight copolymer obtained in Example 1.
Claims (2)
びα−オレフィン成分含量が２５〜７０モル％、 （Ｂ）非共役ジエン成分含量がヨウ素価で３〜１００な
らびに （Ｃ）ポリスチレン換算重量平均分子量が３００〜５０
，０００である、エチレンと炭素数３〜２０のα−オレ
フィンと非共役ジエンとからなるランダム低分子量共重
合体中の非共役ジエン成分の二重結合の１％以上をエポ
キシ化してなるエポキシ化低分子量エチレン−α−オレ
フィン共重合体。(1) (A) ethylene component content of 30 to 75 mol% and α-olefin component content of 25 to 70 mol%, (B) non-conjugated diene component content of 3 to 100 in terms of iodine value, and (C) polystyrene equivalent weight Average molecular weight is 300-50
,000, epoxidized by epoxidizing 1% or more of the double bonds of the non-conjugated diene component in a random low molecular weight copolymer consisting of ethylene, an α-olefin having 3 to 20 carbon atoms, and a non-conjugated diene. Low molecular weight ethylene-α-olefin copolymer.
エポキシ化低分子量エチレン−α−オレフィン共重合体
１〜８０重量部および高分子量エチレン−α−オレフィ
ン共重合体０〜８０重量部を含有してなる熱可塑性樹脂
組成物。(2) 100 parts by weight of thermoplastic resin, 1 to 80 parts by weight of the epoxidized low molecular weight ethylene-α-olefin copolymer according to claim (1), and 0 to 80 parts by weight of the high molecular weight ethylene-α-olefin copolymer. A thermoplastic resin composition containing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2104643A JP3060484B2 (en) | 1990-04-20 | 1990-04-20 | Epoxidized low molecular weight ethylene-α-olefin copolymer and thermoplastic resin composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2104643A JP3060484B2 (en) | 1990-04-20 | 1990-04-20 | Epoxidized low molecular weight ethylene-α-olefin copolymer and thermoplastic resin composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH044204A true JPH044204A (en) | 1992-01-08 |
| JP3060484B2 JP3060484B2 (en) | 2000-07-10 |
Family
ID=14386135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2104643A Expired - Lifetime JP3060484B2 (en) | 1990-04-20 | 1990-04-20 | Epoxidized low molecular weight ethylene-α-olefin copolymer and thermoplastic resin composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3060484B2 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996028514A1 (en) * | 1995-03-10 | 1996-09-19 | Daicel Chemical Industries, Ltd. | Reclaimed thermoplastic resin compositions and process for the production thereof |
| US6031054A (en) * | 1995-12-14 | 2000-02-29 | Dakel Chemical Industries Ltd | Process for producing epoxidized organic polymer, thermoplastic resin composition, primer composition, unvulcanized rubber composition, rubber moldings, and process for producing the molding |
| WO2005058981A1 (en) * | 2003-12-17 | 2005-06-30 | Mitsui Chemicals, Inc. | Epoxidized low-molecular-weight ethylene polymer, mold-releasing agent for electrophotographic toner, and electrophotographic toner for developing electrostatic image |
| JP2006131674A (en) * | 2004-11-02 | 2006-05-25 | Mitsui Chemicals Inc | New polymer and its application |
| WO2022145494A1 (en) * | 2020-12-31 | 2022-07-07 | Brigestone Corporation | Grafted epdm polymers and rubber compositions employing same |
-
1990
- 1990-04-20 JP JP2104643A patent/JP3060484B2/en not_active Expired - Lifetime
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996028514A1 (en) * | 1995-03-10 | 1996-09-19 | Daicel Chemical Industries, Ltd. | Reclaimed thermoplastic resin compositions and process for the production thereof |
| US6031054A (en) * | 1995-12-14 | 2000-02-29 | Dakel Chemical Industries Ltd | Process for producing epoxidized organic polymer, thermoplastic resin composition, primer composition, unvulcanized rubber composition, rubber moldings, and process for producing the molding |
| US6337134B1 (en) | 1995-12-14 | 2002-01-08 | Daicel Chemical Industries Ltd | Process for producing epoxidized organic polymer, thermoplastic resin composition, primer composition, unvulcanized rubber composition, rubber moldings, and process for producing the moldings |
| WO2005058981A1 (en) * | 2003-12-17 | 2005-06-30 | Mitsui Chemicals, Inc. | Epoxidized low-molecular-weight ethylene polymer, mold-releasing agent for electrophotographic toner, and electrophotographic toner for developing electrostatic image |
| JP2006131674A (en) * | 2004-11-02 | 2006-05-25 | Mitsui Chemicals Inc | New polymer and its application |
| JP4643226B2 (en) * | 2004-11-02 | 2011-03-02 | 三井化学株式会社 | Additives for printing inks, solvent dispersions for printing inks, and printing inks |
| WO2022145494A1 (en) * | 2020-12-31 | 2022-07-07 | Brigestone Corporation | Grafted epdm polymers and rubber compositions employing same |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3060484B2 (en) | 2000-07-10 |
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