JPH0480945B2 - - Google Patents
Info
- Publication number
- JPH0480945B2 JPH0480945B2 JP11060584A JP11060584A JPH0480945B2 JP H0480945 B2 JPH0480945 B2 JP H0480945B2 JP 11060584 A JP11060584 A JP 11060584A JP 11060584 A JP11060584 A JP 11060584A JP H0480945 B2 JPH0480945 B2 JP H0480945B2
- Authority
- JP
- Japan
- Prior art keywords
- polyphenylene ether
- group
- ether
- weight
- hydrocarbon residue
- 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 - Lifetime
Links
- 229920001955 polyphenylene ether Polymers 0.000 claims description 50
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 45
- -1 urea compound Chemical class 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 21
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 239000004202 carbamide Substances 0.000 claims description 9
- 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
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 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 20
- 229920001577 copolymer Polymers 0.000 description 20
- 239000011159 matrix material Substances 0.000 description 11
- 229920000098 polyolefin Polymers 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000000465 moulding Methods 0.000 description 8
- 239000004014 plasticizer Substances 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- 229920001112 grafted polyolefin Polymers 0.000 description 7
- 239000011256 inorganic filler Substances 0.000 description 6
- 229910003475 inorganic filler Inorganic materials 0.000 description 6
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 5
- 239000004793 Polystyrene Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920002223 polystyrene Polymers 0.000 description 5
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 238000002156 mixing Methods 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
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-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
- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 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 2
- 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 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 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 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- UPUMJVLEADOLKF-UHFFFAOYSA-N 1,3-bis(3-methylphenyl)urea Chemical compound CC1=CC=CC(NC(=O)NC=2C=C(C)C=CC=2)=C1 UPUMJVLEADOLKF-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-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
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 1
- 244000043261 Hevea brasiliensis Species 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
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 description 1
- 229920000147 Styrene maleic anhydride Polymers 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
- 229920001400 block copolymer Polymers 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
- 238000004581 coalescence Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 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
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000003063 flame retardant Substances 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
- 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
- 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
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 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
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000314 poly p-methyl styrene Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 229920001897 terpolymer Polymers 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
- 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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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, this resin has a high melting temperature and high melt viscosity, so
During molding, high molding temperatures and pressures are required, 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, and It has 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 a mixture of polyphenylene ether or a composition of polyphenylene ether and a styrene resin, and a urea compound represented by the following formula. 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 , R 3 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, an alicyclic hydrocarbon residue, or an aromatic hydrocarbon residue. R2 , R4 : H or a saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, an alicyclic hydrocarbon residue, or an aromatic hydrocarbon residue. (R 1 , R 2 , R 3 , and R 4 may be the same or different.) [] Specific description of the invention (1) Polyphenylene ether The polyphenylene ether used in the present invention is generally 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 Indicates 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-chloro-1,4-phenylene) ether,
Poly(2,5-dibromo-1,4-phenylene) ether and the like. Also, 2,6-dimethylphenol and 2,3,
Copolymer of 6-trimethylphenol, 2,6
- Copolymers such as a copolymer of dimethylphenol and 2,3,5,6-tetramethylphenol and a copolymer of 2,6-diethylphenol and 2,3,6-trimethylphenol can also be mentioned. . Furthermore, the polyphenylene ether used in the present invention is a polyphenylene ether defined by the above general formula and a styrene monomer (for example,
It also includes modified polyphenylene ethers such as those grafted with styrene, p-methylstyrene, α-methylstyrene, etc.). Methods for producing polyphenylene ethers corresponding to the above are known, for example, in US Pat.
Specifications of No. 3306874, No. 3306875, No. 3257357, and No. 3257358 and Japanese Patent Publication No. 1973
-17880 and JP-A-50-51197. A group of polyphenylene ethers preferred for the purposes of the present invention are those with alkyl substituents in the two positions ortho to the ether oxygen atom and those with 2,6-dialkylphenols and 2,6-dialkylphenols.
Copolymers of 3,6-trialkylphenol and also graft polymers obtained by grafting styrene monomers onto these polyphenylene ether skeletons. (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, sterene-butadiene copolymer, and ethylene-propylene. copolymers, high-impact polystyrene modified with various rubbers such as ethylene-propylene-dienterpolymers, styrene-butadiene copolymers, styrene-maleic anhydride copolymers, styrene-acrylonitrile copolymers, styrene-butadiene copolymers,
Examples include acrylonitrile-butadiene copolymer, styrene-methyl methacrylate copolymer, 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 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, a polymer that has been given sensitivity by introducing a polar group can also be used. In addition to using a polymer that has been given sensitivity to a rubber-like elastic polymer, polyethylene, ethylene-vinyl acetate copolymer,
It is also possible to use a polymer obtained by imparting sensitivity to a polyolefin polymer such as polypropylene. 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 silane compound to the above polymer. You can do it by leaning. 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. A special structure is formed in which inorganic fillers are selectively filled in the polymer, and 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 average particle size of the inorganic filler is preferably about 0.05 to 1.0Ό, and it is 0.5 to 60% by weight, preferably 1 to 60% by weight, based on the entire composition obtained by mixing.
45% by weight is used. Furthermore, as other polymers, polyphenylene ether or polyolefin graft-polymerized with a styrene resin can also be used. Polyphenylene ether graft polyolefin is a glycidylated polyphenylene ether obtained by reacting with epichlorohydrin.
Polyolefins having a carboxyl group or an acid anhydride group in the main chain or side chain, such as ethylene/acrylic acid copolymer, ethylene/methacrylic acid copolymer, maleic anhydride-modified polypropylene, maleic anhydride-modified polyethylene, maleic anhydride-modified It can be obtained by grafting onto ethylene/vinyl acetate copolymer or the like. In addition, polyphenylene ether graft polyolefins are polyolefins having glycidyl groups in their side chains, such as ethylene/glycidyl methacrylate copolymers, ethylene/vinyl acetate,
It can also be obtained by grafting polyphenylene ether onto a glycidyl methacrylate copolymer or the like. 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. Coalescence, styrene/itaconic anhydride copolymer, styrene/asconitic anhydride copolymer,
Styrene/acrylic acid copolymer, styrene/methacrylic acid copolymer, etc. are combined with polyolefins having a glycidyl group in the side chain, such as ethylene/glycidyl methacrylate copolymer, ethylene/vinyl acetate/glycidyl methacrylate copolymer, etc. It can be obtained by grafting. The amount added is based on the total amount of polyphenylene ether, or the composition of polyphenylene ether and styrene resin, and the polyphenylene ether grafted polyolefin and/or polystyrene grafted polyolefin.
0.1 to 50% by weight, preferably 1 to 30% by weight of polyphenylene ether grafted polyolefin;
Polystyrene graft polyolefin 1-80
% by weight, preferably in the range from 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, by kneading a composition of glycidyl group-containing polyolefin and polyphenylene ether or polyphenylene ether and styrene resin at high temperature, each component is mixed uniformly and at the same time the graft reaction progresses. A composition containing the polyphenylene ether-grafted polyolefin and/or polystyrene-grafted polyolefin produced by the method can be obtained all at once, and is the most preferred method from an economical point of view. (4) Urea compound The urea compound used in the present invention is represented by the following formula. R 1 , R 3 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, an alicyclic hydrocarbon residue, or an aromatic hydrocarbon residue. R 2 , R 4 : H or a saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms,
Alicyclic hydrocarbon residue or aromatic hydrocarbon residue. (R 1 , R 2 , R 3 , and R 4 may be the same or different.) Examples of R 1 and R 3 include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group,
Isobutyl group, t-butyl group, pentyl group, isopentyl group, cyclopentyl group, hexyl group, isohexyl group, cyclohexyl group, heptyl group, octyl group, decyl group, phenyl group. Examples of R 2 and R 4 include H, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, t-butyl group, pentyl group, isopentyl group, cyclopentyl group, hexyl group, isohexyl group, and cyclohexyl group. basis,
Examples include heptyl group, octyl group, decyl group, and phenyl group. The urea compound of the present invention is intended to be compatible with the matrix component in the fluid state during molding, and to crystallize and phase separate from the matrix component during use. Therefore, it is desirable that the melting point of the urea 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 urea compound used in the present invention has a melting point of 105 to 350°C, preferably 150°C.
It is desirable that the temperature is in the range of â to 300â. However, when the molding temperature is outside the above range due to the addition of a stabilizer or plasticizer, a urea compound having a different melting point can be used accordingly. The amount added is preferably 0.5 to 20 parts by weight, preferably 2 to 10 parts by weight, per 100 parts by weight of all polymers. (5) Additives In the present invention, other additives may be used depending on the purpose. Additives include stabilizers, plasticizers, flame retardants,
There are various inorganic fillers, mold release agents, colorants, etc. The polyphenylene ether composition of the present invention has the advantage of improved fluidity, and has the advantage of being easy to mold even if 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 200000, microgel content 14.5% by weight) 50 parts by weight and the following structural formula: N,N'-dicyclohexylurea (manufactured by Yamato Scientific Co., Ltd., melting point measured with melting point measuring instrument MP-1 type:
232â) and 5 parts by weight at 260â using a Brabender.
The mixture was melt-kneaded for 7.5 minutes. 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'-dicyclohexylurea was not used. Comparative Example 2 Instead of N,N'-dicyclohexylurea,
Plasticizer triphenyl phosphate (melting point:
Table 1 shows the results obtained in the same manner as in Example 1 except that 5 parts by weight (50°C) was used. As is clear from Table 1, by using N,N'-dicyclohexylurea, 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.
ãè¡šã
å®æœäŸ ïŒ
ãNâ²âãžã·ã¯ãããã·ã«ãŠã¬ã¢ã«ä»£ããŠã
ãNâ²âãžïŒïœâããªã«ïŒãŠã¬ã¢ïŒèç¹ïŒ215
âïŒïŒéééšãçšãã以å€ã¯ãå®æœäŸïŒãšåæ§ã«
ããŠåŸãããçµæãè¡šâïŒã«ç€ºãã[Table] Example 2 Instead of N,N'-dicyclohexylurea,
N,N'-di(m-tolyl)urea (melting point: 215
Table 2 shows the results obtained in the same manner as in Example 1, except that 5 parts by weight (°C) was used.
Claims (1)
ãã¬ã³ãšãŒãã«ãšã¹ãã¬ã³ç³»æš¹èãšã®çµæç©ãšã
次åŒã§è¡šãããããŠã¬ã¢ååç©ãšãæ··åããŠãª
ããéåäœ100éééšã«å¯ŸããŠãŠã¬ã¢ååç©ã0.5
ã20éééšã§ããããšãç¹åŸŽãšããæ圢æ§ãæ¹è¯
ããããªããšãã¬ã³ãšãŒãã«çµæç©ã R1ãR3ïŒççŽ æ°ïŒã10ã®çŽéç¶è¥ããã¯åŽéã
æãã飜åã®éç¶çåæ°ŽçŽ æ®åºãèç°åŒçåæ°Ž
çŽ æ®åºãŸãã¯è³éŠæçåæ°ŽçŽ æ®åºã R2ãR4ïŒïŒšè¥ããã¯ççŽ æ°ïŒã10ã®çŽéç¶è¥ã
ãã¯åŽéãæãã飜åã®éç¶çåæ°ŽçŽ æ®åºãè
ç°åŒçåæ°ŽçŽ æ®åºåã¯è³éŠæçåæ°ŽçŽ æ®åºã ïŒR1ãR2ãR3ãR4ã¯ãåäžã§ããç°ãªã€ãŠã
ããïŒ[Scope of Claims] 1. Polyphenylene ether or a composition of polyphenylene ether and styrene resin;
The urea compound represented by the following formula is mixed, and the urea compound is 0.5 parts by weight per 100 parts by weight of the polymer.
20 parts by weight of a polyphenylene ether composition with improved moldability. R 1 , R 3 : A saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, an alicyclic hydrocarbon residue, or an aromatic hydrocarbon residue. R 2 , R 4 : H or a saturated chain hydrocarbon residue having a linear or side chain having 1 to 10 carbon atoms, an alicyclic hydrocarbon residue, or an aromatic hydrocarbon residue. (R 1 , R 2 , R 3 , and R 4 may be the same or different)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11060584A JPS60255849A (en) | 1984-05-30 | 1984-05-30 | Polyphenylene ether composition having improved moldability |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11060584A JPS60255849A (en) | 1984-05-30 | 1984-05-30 | Polyphenylene ether composition having improved moldability |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60255849A JPS60255849A (en) | 1985-12-17 |
| JPH0480945B2 true JPH0480945B2 (en) | 1992-12-21 |
Family
ID=14540075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11060584A Granted JPS60255849A (en) | 1984-05-30 | 1984-05-30 | Polyphenylene ether composition having improved moldability |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60255849A (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
- 1984-05-30 JP JP11060584A patent/JPS60255849A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60255849A (en) | 1985-12-17 |
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