JPH0530863B2 - - Google Patents
Info
- Publication number
- JPH0530863B2 JPH0530863B2 JP10010384A JP10010384A JPH0530863B2 JP H0530863 B2 JPH0530863 B2 JP H0530863B2 JP 10010384 A JP10010384 A JP 10010384A JP 10010384 A JP10010384 A JP 10010384A JP H0530863 B2 JPH0530863 B2 JP H0530863B2
- Authority
- JP
- Japan
- Prior art keywords
- polyphenylene ether
- group
- ether
- weight
- styrene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 53
- 229920001955 polyphenylene ether Polymers 0.000 claims description 48
- -1 diamide compound Chemical class 0.000 claims description 40
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002430 hydrocarbons Chemical group 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 3
- 229920001577 copolymer Polymers 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 22
- 229920001112 grafted polyolefin Polymers 0.000 description 11
- 239000011159 matrix material Substances 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000000465 moulding Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- 239000005977 Ethylene Substances 0.000 description 6
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- 239000000654 additive Substances 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- KLAQSPUVCDBEGF-UHFFFAOYSA-N 2,3,5,6-tetramethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1C KLAQSPUVCDBEGF-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
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-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
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920001890 Novodur Polymers 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 229920000265 Polyparaphenylene Polymers 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 2
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- AUANQXZULGEZQF-UHFFFAOYSA-N 1-n,3-n-bis(2-methylphenyl)benzene-1,3-diamine Chemical compound CC1=CC=CC=C1NC1=CC=CC(NC=2C(=CC=CC=2)C)=C1 AUANQXZULGEZQF-UHFFFAOYSA-N 0.000 description 1
- XRUGBBIQLIVCSI-UHFFFAOYSA-N 2,3,4-trimethylphenol Chemical compound CC1=CC=C(O)C(C)=C1C XRUGBBIQLIVCSI-UHFFFAOYSA-N 0.000 description 1
- METWAQRCMRWDAW-UHFFFAOYSA-N 2,6-diethylphenol Chemical compound CCC1=CC=CC(CC)=C1O METWAQRCMRWDAW-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 description 1
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-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
- 229920002126 Acrylic acid copolymer Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical group C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000005826 halohydrocarbons Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- NWGGAHDZCNJXJA-UHFFFAOYSA-N n-(2-benzamidoethyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NCCNC(=O)C1=CC=CC=C1 NWGGAHDZCNJXJA-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Description
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[1] Background of the Invention The present invention relates to polyphenylene ether compositions, particularly polyphenylene ether compositions with improved moldability. Polyphenylene ether has excellent electrical and mechanical properties, a high heat distortion temperature, and self-extinguishing properties, and is attracting attention as an extremely useful engineering plastic material. However, it has low impact strength and is somewhat brittle. Furthermore, since this resin has a high melting temperature and high melt viscosity, high molding temperatures and pressures are required during molding, making molding by melting difficult. As one method for improving the moldability of polyphenylene ether, attempts have been made to blend it with other resins. For example, Tokuko Sho 43-17812
The publication describes blending a high impact polystyrene resin with polyphenylene ether. Although this composition has improved moldability and impact resistance, it is said that the moldability is still insufficient. Another method to improve the moldability of polyphenylene ether is to add a plasticizer to polyphenylene ether.
For example, Japanese Patent Publication No. 49-5220 describes an aromatic organic acid ester having good compatibility with polyphenylene ether resin, a polyester having an aromatic group, an organic phosphate ester having an aromatic group, It has also been shown that moldability can be improved by blending a compound selected from chlorinated aromatic hydrocarbons into polyphenylene ether or a composition of polyphenylene ether and styrenic resin. . However, when a plasticizer (for example, an organic phosphate ester having an aromatic group) is blended with polyphenylene ether or a composition of polyphenylene ether and styrene resin, moldability is improved, but performance will be significantly reduced. this is,
Because the blended plasticizer is extremely uniformly dispersed (molecularly dispersed) in a matrix made of polyphenylene ether or a composition of polyphenylene ether and styrene resin, the glass transition temperature (Tg) of the matrix is ) is considered to decrease, resulting in a decrease in heat resistance. The present inventors considered that it is desirable for the additive to have the following properties in order to suppress this decrease in thermal performance (heat resistance) and improve moldability (fluidity). (1) During molding, that is, under the fluid state of the system, it must have good compatibility with matrix components and exhibit the same fluidity-improving effect as a plasticizer. (2) During use, i.e. under flow stopped conditions (matrix
(temperature range below Tg), it should phase separate from the matrix components and do not lower the Tg of the matrix. However, in order to prevent a decrease in mechanical strength, the interfacial adhesive force with the matrix must be strong to a certain extent even when phase separation occurs, and the material must have affinity with the matrix. The present inventors have arrived at the present invention as a result of intensive studies from this viewpoint. [] Summary of the invention The present invention provides polyphenylene ether, or
The object of the present invention is to provide a means for improving the moldability of a composition of polyphenylene ether and styrene resin. That is, the present invention is made by mixing polyphenylene ether or a composition of polyphenylene ether and styrene resin with a diamide compound represented by the following formula, and the diamide compound is mixed with respect to 100 parts by weight of the polymer. The present invention provides a polyphenylene ether composition with improved moldability, characterized in that the compound is contained in an amount of 0.5 to 20 parts by weight. R 1 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 20 carbon atoms, or an aromatic hydrocarbon residue. R 2 , R 3 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, or an aromatic hydrocarbon residue, or an aromatic hydrocarbon substituted with the following substituent: Derivative residue. (R 2 and R 3 may be the same or different) -R 4 (R 4 : methyl group) [] Specific description of the invention (1) Polyphenylene ether Polyphenylene used in the present invention Ether has the general formula The ether oxygen atom of one unit is connected to the benzene nucleus of the next adjacent unit, n is at least 50, and Q is each independently hydrogen, halogen, Hydrocarbon groups containing no tertiary α-carbon atoms, halohydrocarbon groups having at least two carbon atoms between the halogen atom and the phenyl nucleus, hydrocarbonoxy groups and between the halogen atom and the phenyl nucleus represents a monovalent substituent selected from the group consisting of halohydrocarbonoxy groups having at least 2 carbon atoms. Typical examples of polyphenylene ether include poly(2,6-dimethyl-1,4-phenylene) ether, poly(2,6-diethyl-1,4
-phenylene)ether, poly(2-methyl-6)
-ethyl-1,4-phenylene) ether, poly(2-methyl-6-propyl-1,4-phenylene) ether, poly(2,6-dipropyl-1,
4-phenylene)ether, poly(2-ethyl-
6-propyl-1,4-phenylene) ether,
Poly(2,6-dibutyl-1,4-phenylene)
Ether, poly(2,6-dipropenyl-1,4
-phenylene) ether, poly(2,6-dilauryl-1,4-phenylene) ether, poly(2,6-diphenyl-1,4-phenylene) ether, poly(2,6-dimethoxy-1,4-phenylene) ) ether, poly(2,6-diethoxy-1,4-phenylene) ether, poly(2-methoxy-6-ethoxy-1,4-phenylene) ether, poly(2-ethyl-6-stearyloxy-1, 4-phenylene)ether, poly(2,
6-dichloro-1,4-phenylene)ether,
Poly(2-methyl-6-phenyl-1,4-phenylene) ether, poly(2,6-dibenzyl-
1,4-phenylene) ether, poly(2-ethoxy-1,4-phenylene) ether, poly(2-phenylene) ether,
-chloro-1,4-phenylene) ether, poly(2,5-dibromo-1,4-phenylene) ether and the like. Also, 2,6-dimethylphenol and 2,3,6
-Copolymer of trimethylphenol, copolymer of 2,6-dimethylphenol and 2,3,5,6-tetramethylphenol, copolymer of 2,6-diethylphenol and 2,3,6-trimethylphenol Mention may also be made of copolymers such as polymers. Furthermore, the polyphenylene ether used in the present invention is a polyphenylene ether defined by the above general formula grafted with a styrenic monomer (for example, styrene, p-methylstyrene, α-methylstyrene, etc.). Also included are modified polyphenylene ethers. Methods for producing polyphenylene ethers corresponding to the above are known, for example, US Pat. No. 3,306,874;
It is described in each specification of No. 3306875, No. 3257357, and No. 3257358, and the specification of Japanese Patent Publication No. 52-17880 and Japanese Patent Application Laid-open No. 50-51197. Preferred groups of polyphenylene ethers for the purposes of the present invention are those with alkyl substituents in the two ortho positions to the ether oxygen atom and co-containers of 2,6-dialkylphenols and 2,3,6-trialkylphenols. Further, the polymer is a graft polymer obtained by grafting a styrene monomer onto the polyphenylene ether skeleton. (2) Styrenic resin The styrene resin used in the present invention includes homopolymers such as polystyrene, poly-α-methylstyrene, and poly-p-methylstyrene, butadiene rubber, styrene-butadiene copolymer, and ethylene-propylene. copolymers, high-impact polystyrene modified with various rubbers such as ethylene-propylene-dient terpolymers, styrene-butadiene copolymers, styrene-butadiene copolymers,
Maleic anhydride copolymer, styrene/acrylonitrile copolymer, styrene/acrylonitrile/
There are butadiene copolymers, styrene/methyl methacrylate copolymers, etc., and these styrene resins are mixed in a proportion of 0 to 2000 parts by weight with respect to 100 parts by weight of the polyphenylene ether resin. (3) Addition of other polymers Other polymers can be added to polyphenylene ether or a composition of polyphenylene ether and styrene resin for the purpose of improving impact resistance. Polymers to be added include natural or synthetic rubber-like elastomeric polymers, such as natural rubber, polyisoprene, polybutadiene, copolymers of styrene and conjugated dienes such as butadiene (including block copolymers), Ethylene-propylene copolymers, ethylene-propylene-nonconjugated diene terpolymers, etc. can be used. In addition, polymers that have been imparted with sensitivity by introducing polar groups can also be used, such as rubber-like elastic polymers that have been imparted with sensitivity, as well as polyethylene, ethylene-vinyl acetate copolymers, polypropylene, etc. It is also possible to use a polymer obtained by imparting sensitivity to the polyolefin polymer described above. As a means of imparting sensitivity, it is possible to graft an unsaturated organic acid or its anhydride (for example, acrylic acid, methacrylic acid, maleic acid, itaconic acid, or anhydride thereof) or an unsaturated silanized product to the above polymer. This can be done by Furthermore, a polymer imparted with sensitivity can also be obtained by block or random polymerization of ethylene with a vinyl monomer or vinyl silane having a polar group such as an unsaturated organic acid such as acrylic acid or an ester thereof. . When using rubber-modified polystyrene, the amount of the rubber-like elastic polymer or the polymer imparted with sensitivity is such that the total amount including the rubber content derived from it is 0.5 to 50% by weight based on the total amount of all polymer components. %, preferably about 2 to 40% by weight. Further, when using a polymer imparted with sensitivity, it is preferable to add an inorganic filler.
When a sensitized polymer and an inorganic filler are used together, the sensitized polymer is dispersed in the matrix of polyphenylene ether or a composition of polyphenylene ether and styrene resin, imparting sensitivity. Forms a special structure in which inorganic filler is selectively filled in the polymer.
Excellent physical properties such as mechanical strength can be obtained. As the inorganic filler, inorganic powders known as fillers for synthetic resins, such as titanium oxide, zinc oxide, talc, clay, calcium carbonate, and silica, can be used. The inorganic filler preferably has an average particle size of about 0.05 to 1.0 ÎŒm, and is used in an amount of 0.5 to 60% by weight, preferably 1 to 45% by weight, based on the entire composition obtained by mixing. Furthermore, as other polymers, polyphenylene ether or polyolefin graft-polymerized with a styrene resin can also be used. Polyphenylene ether grafted polyolefin is a polyolefin that has a carboxyl group or an acid anhydride group in the main chain or side chain, such as ethylene/acrylic acid copolymer, ethylene. - Can be obtained by grafting onto methacrylic acid copolymer, maleic anhydride-modified polypropylene, maleic anhydride-modified polyethylene, maleic anhydride-modified ethylene/vinyl acetate copolymer, etc. In addition, polyphenylene ether grafted polyolefin is obtained by grafting polyphenylene ether onto a polyolefin having a glycidyl group in its side chain, such as ethylene/glycidyl methacrylate copolymer, ethylene/vinyl acetate/glycidyl methacrylate copolymer, etc. It can also be obtained by Polystyrene-grafted polyolefins include styrene-based copolymers having a carboxylic acid group or cyclic acid anhydride group in the main chain or side chain of polystyrene, such as styrene/maleic anhydride copolymer, styrene/citraconic anhydride copolymer, etc. Union,
Styrene/itaconic anhydride copolymer, styrene/itaconic anhydride copolymer,
Asconitic anhydride copolymer, styrene/itaconic anhydride copolymer, styrene/asconitic anhydride copolymer, styrene/acrylic acid copolymer, styrene/methacrylic acid copolymer, etc. have glycidyl groups in their side chains. It can be obtained by grafting polyolefins such as ethylene/glycidyl methacrylate copolymer, ethylene/vinyl acetate/glycidyl methacrylate copolymer, etc. The amount added is polyphenylene ether or
Based on the composition of polyphenylene ether and styrene resin, and the total amount of polyphenylene ether grafted polyolefin and/or polystyrene grafted polyolefin, the amount of polyphenylene ether grafted polyolefin is 0.1 to 50% by weight, preferably 1 to 50% by weight. 30% by weight, polystyrene-grafted polyolefin in a range of 1 to 80% by weight, preferably 1 to 30% by weight. The grafted polyolefin can be added after graft polymerization in advance, but when using a polyolefin having a glycidyl group, it can be added to a polyphenylene ether or a styrene resin having a carboxylic acid or its anhydride group. The graft reaction can be carried out by kneading at a high temperature of .degree. C. or higher. Therefore, a glycidyl group-containing polyolefin,
By kneading polyphenylene ether or a composition of polyphenylene and styrene resin at high temperature, each component is mixed uniformly, and at the same time, a polyphenylene ether grafted polyolefin is produced by progressing the graft reaction. A composition containing polystyrene-grafted polyolefin and/or polystyrene-grafted polyolefin can be obtained all at once, and is the most preferable method from an economical point of view. (4) Diamide compound The diamide compound used in the present invention is represented by the following formula. R1 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 20 carbon atoms, or an aromatic hydrocarbon residue. R 2 , R 3 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, or an aromatic hydrocarbon residue, or an aromatic hydrocarbon substituted with the following substituent: Derivative residue. (R 2 and R 3 may be the same or different) -R 4 (R 4 : methyl group) R 1 is, for example, a methylene group, an ethylene group,
Examples include trimethylene group, propylene group, tetramethylene group, isobutylene group, pentamethylene group, hexamethylene group, octamethylene group, decamethylene group, phenylene group, naphthalene group, biphenylene group, and diphenylenemethane group. Examples of R 2 and R 3 include methyl group, ethyl group,
Examples include propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, isopentyl group, hexyl group, isohexyl group, heptyl group, octyl group, decyl group, phenyl group, and the like. The diamide compound of the present invention is intended to be compatible with the matrix component under the fluid state during molding, and crystallize and phase separate from the matrix component when used. Therefore, it is desirable that the melting point of the diamide compound of the present invention is slightly lower than the molding temperature. Generally, the molding temperature of the polyphenylene ether composition is 105-350°C, preferably 200-300°C. Therefore, the diamide compound used in the present invention has a melting point of 105 to 350°C, preferably 150°C to
It is desirable that the temperature be within the range of 300â. However, when the molding temperature is outside the above range due to the addition of a stabilizer or plasticizer, a diamide compound having a different melting point can be used accordingly. The amount added is 100 parts by weight of all polymers,
0.5 to 20 parts by weight, preferably 2 to 10 parts by weight. (5) Additives In the present invention, other additives may be used depending on the purpose. Examples of additives include stabilizers, plasticizers, flame retardants, various inorganic fillers, mold release agents, and colorants. The polyphenylene ether composition of the present invention has the advantage of improved fluidity, and has the advantage of being easy to mold even when other additives are added. [] Examples The present invention will be specifically described below with reference to Examples. Example 1 50 parts by weight of poly-2,6-dimethyl-1,4-phenylene ether (manufactured by Mitsubishi Yuka Co., Ltd., intrinsic viscosity 0.50 in chloroform at 25°C) and high impact polystyrene (manufactured by Mitsubishi Yuka Co., Ltd., several parts by weight) Average molecular weight 55000,
Weight average molecular weight 20000, microgel content 14.5% by weight) 50 parts by weight and the following structural formula. 5 parts by weight of N,N'-dihepetanoyl-P-phenylenediamine (manufactured by Yamato Kagaku Co., Ltd., melting point measured with melting point meter MP-1 model; 211°C) was melted at 260°C for 7.5 minutes using a Brabender. Kneaded. After kneading, the melt index (250â, 10Kg load) indicating moldability (fluidity) was measured, and a specified test piece was made using a press, and the heat distortion temperature was measured (18.6Kg/cm 2 loads).
The results are shown in Table-1. Comparative Example 1 Table 1 shows the results obtained in the same manner as in Example 1 except that N,N'-diheptanoyl-P-phenylenediamine was not used. Comparative Example 2 Obtained in the same manner as in Example 1, except that 5 parts by weight of triphenyl phosphate (melting point: 50°C) as a plasticizer was used in place of N,N'-diheptanoyl-P-phenylenediamine. Table 1 shows the results.
Shown below. As is clear from Table 1, by using N,N'-diheptanoyl-P-phenylenediamine, the fluidity (moldability) is significantly improved and the decrease in heat resistance is suppressed. Although the plasticizer improves the fluidity, the heat resistance is greatly reduced, and the effect of the present invention can be understood.
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è¡šâïŒã«ç€ºãã[Table] Example 2 Same as Example 1 except that 5 parts by weight of N,N'-dibenzoylethylenediamine (melting point: 244°C) was used instead of N,N'-diheptanoyl-P-phenylenediamine. The results obtained are shown below.
Shown in 2. Example 3 Instead of N,N'-diheptanoyl-P-phenylenediamine, N,N'-dibenzoyl-m-
Table 2 shows the results obtained in the same manner as in Example 1 except that 5 parts by weight of phenylenediamine (melting point: 213°C) was used. Example 4 Same as Example 1 except that 5 parts by weight of N,N'-ditolyl-m-phenylenediamine (melting point: 186°C) was used instead of N,N'-diheptanoyl-P-phenylenedimine. The results obtained are shown in Table-2.
Claims (1)
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次åŒã§è¡šãããããžã¢ããååç©ãšãæ··åããŠãª
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æ¹è¯ããããªããšãã¬ã³ãšãŒãã«çµæç©ã R1ïŒççŽ æ°ïŒã20ã®çŽéç¶è¥ããã¯åŽéãæ
ãã飜åã®éç¶çåæ°ŽçŽ æ®åºããŸãã¯è³éŠ
æçåæ°ŽçŽ æ®åºã R2ïŒR3ïŒççŽ æ°ïŒã10ã®çŽéç¶è¥ããã¯åŽé
ãæãã飜åã®éç¶çåæ°ŽçŽ æ®åºããŸãã¯
è³éŠæçåæ°ŽçŽ æ®åºãããã¯ã次ã®çœ®æåº
ã§çœ®æãããè³éŠæçåæ°ŽçŽ èªå°äœæ®åºã ïŒR2ïŒR3ã¯ãåäžã§ããç°ãªã€ãŠãããïŒ âR4 ïŒR4ïŒã¡ãã«åºïŒ[Scope of Claims] 1. Polyphenylene ether or a composition of polyphenylene ether and styrene resin;
It is made by mixing a diamide compound represented by the following formula, and the diamide compound is mixed with 100 parts by weight of the polymer.
A polyphenylene ether composition with improved moldability, characterized in that the amount is 0.5 to 20 parts by weight. R 1 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 20 carbon atoms, or an aromatic hydrocarbon residue. R 2 , R 3 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, or an aromatic hydrocarbon residue, or an aromatic hydrocarbon substituted with the following substituent: Derivative residue. (R 2 and R 3 may be the same or different) -R 4 (R 4 : methyl group)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10010384A JPS60245667A (en) | 1984-05-18 | 1984-05-18 | Polyphenylene ether composition having improved moldability |
| US06/732,599 US4663375A (en) | 1984-05-15 | 1985-05-10 | Process for producing heat-resisting moldings |
| EP85303426A EP0162663B1 (en) | 1984-05-15 | 1985-05-15 | Process for producing heat-resistant moldings |
| DE8585303426T DE3583888D1 (en) | 1984-05-15 | 1985-05-15 | METHOD FOR PRODUCING HEAT-RESISTANT MOLDED PARTS. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10010384A JPS60245667A (en) | 1984-05-18 | 1984-05-18 | Polyphenylene ether composition having improved moldability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60245667A JPS60245667A (en) | 1985-12-05 |
| JPH0530863B2 true JPH0530863B2 (en) | 1993-05-11 |
Family
ID=14265050
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10010384A Granted JPS60245667A (en) | 1984-05-15 | 1984-05-18 | Polyphenylene ether composition having improved moldability |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60245667A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0788466B2 (en) * | 1986-10-14 | 1995-09-27 | äœåããŠæ ªåŒäŒç€Ÿ | Polyphenylene ether heat-resistant resin composition |
-
1984
- 1984-05-18 JP JP10010384A patent/JPS60245667A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60245667A (en) | 1985-12-05 |
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| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |