CN100363425C - 粉末形式的含聚亚芳基醚的热固性组合物、其制备方法以及由其制得的制品 - Google Patents
粉末形式的含聚亚芳基醚的热固性组合物、其制备方法以及由其制得的制品 Download PDFInfo
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- CN100363425C CN100363425C CNB018231004A CN01823100A CN100363425C CN 100363425 C CN100363425 C CN 100363425C CN B018231004 A CNB018231004 A CN B018231004A CN 01823100 A CN01823100 A CN 01823100A CN 100363425 C CN100363425 C CN 100363425C
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- Prior art keywords
- alkyl
- curable resin
- resin composition
- poly
- arylene ether
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 239000000843 powder Substances 0.000 title claims abstract description 31
- -1 Poly (arylene ether Chemical compound 0.000 title claims description 151
- 239000000203 mixture Substances 0.000 title claims description 106
- 238000000034 method Methods 0.000 title claims description 24
- 229920001187 thermosetting polymer Polymers 0.000 title abstract description 12
- 238000002360 preparation method Methods 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims abstract description 68
- 229920005989 resin Polymers 0.000 claims abstract description 46
- 239000011347 resin Substances 0.000 claims abstract description 46
- 239000011342 resin composition Substances 0.000 claims abstract description 32
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 16
- 239000000945 filler Substances 0.000 claims description 15
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000004641 (C1-C12) haloalkyl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 150000002825 nitriles Chemical class 0.000 claims description 7
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- 150000003566 thiocarboxylic acids Chemical class 0.000 claims description 7
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical group CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- 235000013824 polyphenols Nutrition 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 150000008442 polyphenolic compounds Chemical class 0.000 claims description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 claims 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 claims 2
- PCLLJCFJFOBGDE-UHFFFAOYSA-N (5-bromo-2-chlorophenyl)methanamine Chemical compound NCC1=CC(Br)=CC=C1Cl PCLLJCFJFOBGDE-UHFFFAOYSA-N 0.000 claims 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 claims 1
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 claims 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims 1
- NKIDFMYWMSBSRA-UHFFFAOYSA-N [4-(2-methylprop-2-enoyloxymethyl)cyclohexyl]methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1CCC(COC(=O)C(C)=C)CC1 NKIDFMYWMSBSRA-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 229940119545 isobornyl methacrylate Drugs 0.000 claims 1
- 238000012545 processing Methods 0.000 abstract description 5
- 229920000412 polyarylene Polymers 0.000 abstract description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 abstract 1
- 125000000746 allylic group Chemical group 0.000 abstract 1
- 238000001723 curing Methods 0.000 description 18
- 239000000835 fiber Substances 0.000 description 17
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 239000003153 chemical reaction reagent Substances 0.000 description 10
- 239000000523 sample Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002245 particle Substances 0.000 description 9
- 239000000654 additive Substances 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 238000000465 moulding Methods 0.000 description 6
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- 150000004808 allyl alcohols Chemical class 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 4
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000003082 abrasive agent Substances 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 4
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 4
- 229910010271 silicon carbide Inorganic materials 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
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- 235000019580 granularity Nutrition 0.000 description 3
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000000395 magnesium oxide Substances 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
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- 229910052618 mica group Inorganic materials 0.000 description 3
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- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 2
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- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
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- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- HGTUJZTUQFXBIH-UHFFFAOYSA-N (2,3-dimethyl-3-phenylbutan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C)(C)C(C)(C)C1=CC=CC=C1 HGTUJZTUQFXBIH-UHFFFAOYSA-N 0.000 description 1
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- BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明涉及一种可固化树脂组合物，它含有聚亚芳基醚、烯丙基单体和丙烯酰基单体，所述组合物是粉末。该树脂组合物显示改进的韧性，可用于在其中优选使用粉末树脂的热固性材料加工应用。
Description
发明背景
含有聚亚芳基醚树脂的热固性组合物已经描述在美国专利申请系列号09/452733中(1999年12月1日递交)。这些组合物显示优异的性能平衡，包括耐热性、劲度和韧性。但是，已知的含有聚亚芳基醚树脂的热固性组合物通常以粘性液体或糊料的形式存在，这使得它们不适合其中优选可固化粉末的加工方法。
虽然粉末形式的可固化树脂组合物(例如包含酚醛树脂的那些)是已知的，但是对于某些应用，这些组合物欠缺一种或多种性能，例如耐热性、劲度和韧性。需要一种显示改进的后固化性能平衡的粉末形式的可固化热固性组合物。
本发明的简述
本文公开了关于可固化树脂组合物、其制备方法、通过固化所述可固化树脂组合物所形成的反应产物以及由可固化树脂组合物形成的制品的几个实施方案。
一个实施方案是一种可固化树脂组合物，它含有聚亚芳基醚、烯丙基单体和丙烯酰基单体；其中所述组合物是粉末。
另一个实施方案是一种可固化树脂组合物，它含有含聚亚芳基醚、烯丙基单体和丙烯酰基单体的可固化树脂组合物的反应产物；其中所述可固化树脂组合物是粉末。
再一个实施方案是一种含有所述可固化树脂组合物的反应产物的制品。
另一个实施方案是一种形成可固化树脂组合物的方法，包括：使聚亚芳基醚和烯丙基单体共混形成第一紧密共混物；使第一紧密共混物与丙烯酰基单体共混，形成第二紧密共混物；并加工第二紧密共混物，形成可固化的粉末。
优选实施方案的详细描述
一种可固化树脂组合物含有：
聚亚芳基醚；
烯丙基单体；和
丙烯酰基单体，
其中所述组合物是粉末。
该组合物可以包含任何聚亚芳基醚。术语“聚亚芳基醚”包括聚亚苯基醚(PPE)和聚亚芳基醚共聚物；接枝共聚物；聚亚芳基醚离聚物；以及链烯基芳族化合物、乙烯基芳族化合物和聚亚芳基醚的嵌段共聚物，等；以及含有上述至少一种物质的混合物等。聚亚芳基醚是已知的聚合物，包含多个下式的结构单元：
其中对于每个结构单元，每个Q1独立地是卤素，伯或仲C1-C12烷基，苯基，C1-C12卤代烷基，C1-C12氨基烷基，C1-C12烃氧基，或C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子；和每个Q2独立地是氢，卤素，伯或仲C1-C12烷基，苯基，C1-C12卤代烷基，C1-C12氨基烷基，C1-C12烃氧基，或C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子。优选的是，每个Q1独立地是C1-C12烷基或苯基，特别是C1-C4烷基，和每个Q2独立地是氢或甲基。
聚亚芳基醚均聚物和共聚物都包括在本发明中。在一个实施方案中，聚亚芳基醚是包含2，6-二甲基-1，4-亚苯基醚单元的均聚物。合适的共聚物包括无规共聚物，例如包含这种单元与2，3，6-三甲基-1，4-亚苯基醚单元的组合，或由2，6-二甲基苯酚与2，3，6-三甲基苯酚的共聚反应得到的共聚物。还包括含有通过接枝乙烯基单体或聚合物(例如聚苯乙烯)制备的部分的聚亚芳基醚，以及偶联的聚亚芳基醚，其中偶联剂例如是低分子量聚碳酸酯、醌、杂环化合物和缩甲醛，它们与两个聚亚芳基醚链的羟基反应，获得高分子量聚合物。聚亚芳基醚还包括任何上述物质的组合。
聚亚芳基醚通常通过将至少一种单羟基芳族化合物例如2，6-二甲苯酚或2，3，6-三甲基苯酚进行氧化偶联来制备。催化剂体系通常用于这种偶联；它们通常含有至少一种重金属化合物，例如铜、锰或钴化合物，通常与各种其它物质组合使用。合适的制备并分离聚亚芳基醚的方法描述在例如授予Blanchard等人的美国专利3219625，授予Hay的美国专利3306875，授予Hay的美国专利4028341，授予Bennett的美国专利4092294，授予Bartmann等人的美国专利4440923，和授予Aycock等人的美国专利5922815。
在一个实施方案中，所述组合物含有具有低于500份/百万(ppm)的游离羟基的聚亚芳基醚。换句话说，聚亚芳基醚含有低于500微克的羟基(-OH)/每克聚亚芳基醚。聚亚芳基醚优选含有低于300ppm的游离羟基，更优选含有低于100ppm的游离羟基。
在一个实施方案中，所述组合物含有封端的聚亚芳基醚，在这里定义为这样一种聚亚芳基醚，其中在相应未封端的聚亚芳基醚中存在的游离羟基的至少50％、优选至少75％、更优选至少90％、再更优选至少95％、进一步更优选至少99％已经通过与封端剂的反应而被脱除。
封端的聚亚芳基醚可以由下面的结构表示：
Q-(J-K)y，
其中Q是一元、二元或多元酚的残基，优选一元或二元酚的残基，更优选一元酚的残基；y是1-100；J包含具有下面结构的重复单元：
其中m是1至约200，优选2至约200，R1-R4各自独立地是氢，卤素，伯或仲C1-C12烷基、C2-C12链烯基、C2-C12炔基、C1-C12氨基烷基、C1-C12羟烷基、苯基、C1-C12卤代烷基、C1-C12氨基烷基、C1-C12烃氧基，或C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子等；和K是通过聚亚芳基醚上的酚羟基与封端剂反应而获得的封端基团。所得的封端基团可以是：
-Y-R5，
，和
其中R5是C1-C12烷基，R6-R8各自独立地是氢、C1-C12烷基、C2-C12链烯基、C6-C18芳基、C7-C18混合的(烷基-芳基)、C2-C12烷氧基羰基、C7-C18芳氧基羰基、C8-C18混合的(烷基-芳基)氧基羰基、腈、甲酰基、羧酸根、亚氨酸根，硫代羧酸根，等；R9-R13各自独立地是氢，卤素，C1-C12烷基，羟基，氨基等；和其中Y是具有下面结构的二价基团：
其中R14和R15各自独立地是氢，C1-C12烷基等。
在一个实施方案中，Q是酚的残基，包括多官能酚，并包括下面结构的基团：
其中R1-R4各自独立地是氢，卤素，伯或仲C1-C12烷基，C2-C12链烯基，C2-C12炔基、C1-C12氨基烷基、C1-C12羟烷基、苯基、C1-C12卤代烷基、C1-C12氨基烷基、C1-C12烃氧基、C2-C12卤代烃氧基、其中至少两个碳原子隔开卤原子和氧原子、等；X是氢、C1-C20烷基、C6-C20芳基、C7-C20混合的烷基-芳基烃，或含有取代基例如羧酸、醛、醇、氨基的烃基等；X还可以是硫、磺酰基、砜基、氧或其它具有2或更高化合价的桥基，得到各种二-或高级多元酚；y和n各自独立地是1至约100，优选1-3，更优选1-2。在一个优选的实施方案中，y＝n。
在一个实施方案中，封端的聚亚芳基醚通过将基本上由至少一种具有以下结构的一元酚的聚合产物构成的聚亚芳基醚封端来制备：
其中R1-R4各自独立地是氢，卤素，伯或仲C1-C12烷基，C2-C12链烯基，C2-C12炔基，C1-C12氨基烷基，C1-C12羟烷基，苯基，C1-C12卤代烷基，C1-C12氨基烷基，C1-C12烃氧基，C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子，等。合适的一元酚包括在授予Hay的美国专利3306875中描述的那些，以及高度优选的一元酚包括2，6-二甲基苯酚和2，3，6-三甲基苯酚。
在一个实施方案中，封端的聚亚芳基醚包含至少一个具有下面结构的封端基团：
其中R6-R8各自独立地是氢，C1-C12烷基，C2-C12链烯基，C6-C18芳基，C7-C18混合的(烷基-芳基)，C2-C12烷氧基羰基，C7-C18芳氧基羰基，C8-C18混合的(烷基-芳基)氧基羰基，腈，甲酰基，羧酸根，亚氨酸根(imidate)，硫代羧酸根，等。高度优选的封端基团包括丙烯酸根(R6＝R7＝R8＝氢)和甲基丙烯酸根(R6＝甲基，R7＝R8＝氢)。
在一个实施方案中，封端的聚亚芳基醚包含至少一个具有下面结构的封端基团：
其中R5是C1-C12烷基，优选C1-C6烷基，更优选甲基、乙基或异丙基。已经令人惊奇地发现，即使当封端的聚亚芳基醚缺乏可聚合的官能团例如碳-碳双键时也能达到所述组合物的有利性能。
在另一个实施方案中，封端的聚亚芳基醚包含至少一个具有下面结构的封端基团：
其中R9-R13各自独立地是氢，卤素，C1-C12烷基，羟基，氨基等。优选的这种封端基团包括水杨酸根(R9是羟基，R10-R13是氢)。
在一个实施方案中，封端的聚亚芳基醚基本上不含氨基取代基，包括烷基氨基和二烷基氨基取代基，其中“基本上不含”表示封端的聚亚芳基醚含有少于约300微克、优选少于约200微克、更优选少于约100微克的氮原子/每克封端的聚亚芳基醚。尽管许多聚亚芳基醚通过引入氨基取代基的方法来合成，但是已经发现当封端的聚亚芳基醚基本上不含氨基取代基时，热固性材料的固化速率得到提高。基本上不含氨基取代基的聚亚芳基醚可以直接合成或通过将氨基取代的聚亚芳基醚加热到至少约200℃来合成。或者，如果封端的聚亚芳基醚含有氨基取代基，则希望在低于约200℃的温度下固化该组合物。
对制备封端的聚亚芳基醚的方法没有特殊限制。封端的聚亚芳基醚可以通过未封端的聚亚芳基醚与封端剂反应来形成。封端剂包括能与酚基团反应的化合物。这些化合物包括单体和聚合物，它们含有例如酸酐基团、酰氯基团、环氧基团、碳酸酯基团、酯基团、异氰酸酯基团、氰酸酯基团、烷基卤基团，或包含至少一种上述基团的组合。封端剂不限于有机化合物，例如也包括基于磷和硫的封端剂。封端剂例如包括乙酸酐、琥珀酸酐、马来酸酐、水杨酸酐、含水杨酸酯单元的聚酯、水杨酸的聚酯均聚物、丙烯酸酐、甲基丙烯酸酐、丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯、乙酰氯、苯甲酰氯、碳酸二苯基酯例如碳酸二(4-硝基苯基)酯、丙烯酰基酯、甲基丙烯酰基酯、乙酰基酯、苯基异氰酸酯、3-异丙烯基-α，α-二甲基苯基异氰酸酯、氰氧基苯、2，2-双(4-氰氧基苯基)丙烷、3-(α-氯甲基)苯乙烯、4-(α-氯甲基)苯乙烯、烯丙基溴、等等，碳酸酯以及其取代衍生物，以及含有上述至少一种封端剂的混合物。这些和其它形成封端聚亚芳基醚的方法描述在例如授予Holoch等人的美国专利3375228；授予Gossens的美国专利4148843；授予Percec等人的美国专利4562243、4663402、4665137和5091480；授予Nelissen等人的美国专利5071922、5079268、5304600和5310820；授予Vianello等人的美国专利5338796，和授予Peters等人的欧洲专利261574B1。
封端催化剂可以在未封端的聚亚芳基醚与酸酐的反应中使用。这些化合物的例子包括能催化酚类与上述封端剂反应的那些化合物。有用的物质是碱性化合物，包括例如碱性氢氧化物盐，例如氢氧化钠、氢氧化钾、四烷基氢氧化铵等；三烷基胺，例如三丁基胺、三乙基胺、二甲基苄基胺、二甲基丁基胺、等；三元混合的烷基-芳基胺，以及其取代衍生物，例如二甲基苯胺等；杂环胺，例如咪唑、吡啶，以及其取代衍生物，例如2-甲基咪唑、2-乙烯基咪唑、4-(二甲基氨基)-吡啶、4-(1-吡咯啉基)-吡啶、4-(1-哌啶子基)-吡啶、2-乙烯基吡啶、3-乙烯基吡啶、4-乙烯基吡啶、等；和包含至少一种上述物质的混合物。也有用的是有机金属盐，例如已知用于催化例如异氰酸酯或氰酸酯与酚之间的缩合反应的锡和锌盐。在这方面有用的有机金属盐已描述在本领域技术人员已知的许多出版物和专利中。
所述组合物可以含有至少两种封端聚亚芳基醚的共混物。这些共混物可以由单独制备和分离的封端聚亚芳基醚来生产。或者，这些共混物可以通过单个聚亚芳基醚与至少两种封端剂反应来制备。
对聚亚芳基醚的分子量或特性粘数没有特殊的限制。在一个实施方案中，于25℃在氯仿中测得的特性粘数可以是至少约0.1分升/克(dL/g)，优选至少约0.15dL/g，更优选至少约0.20dL/g。特性粘数可以至多为约0.50dL/g，优选至多约0.45dL/g，更优选至多约0.40dL/g，进一步更优选至多约0.35dL/g。一般来说，封端的聚亚芳基醚的特性粘数与相应的未封端聚亚芳基醚的特性粘数之间的区别不大。应该考虑使用至少两种具有不同分子量和特性粘数的封端聚亚芳基醚的共混物。
在所述组合物中，聚亚芳基醚的含量至少为约10重量份，优选至少为约15重量份，更优选至少为约20重量份，基于每100重量份树脂计。在所述组合物中，聚亚芳基醚的含量至多为约50重量份，优选至多为约45重量份，更优选至多为约40重量份，基于每100重量份树脂计。应该理解的是，这里使用的“100重量份树脂”是指树脂组分例如聚亚芳基醚、丙烯酰基单体和磨料的组合重量份；它排除了非树脂组分例如磨料和任何第二填料或固化催化剂。
所述组合物还含有丙烯酰基单体。丙烯酰基单体含有至少一个具有以下结构的丙烯酰基部分：
其中R16和R17各自独立地是氢或C1-C12烷基，其中R16和R17可以位于双键的顺式或反式位置。优选的是，R16和R17各自独立地是氢或甲基。在一个实施方案中，丙烯酰基单体含有至少两个具有以上结构的丙烯酰基部分，称为多官能丙烯酰基单体。在另一个实施方案中，丙烯酰基单体含有至少三个具有以上结构的丙烯酰基部分。
在一个实施方案中，丙烯酰基单体含有至少一个具有下面结构的丙烯酰基部分：
其中R18-R20各自独立地是氢，C1-C12烷基，C2-C12链烯基，C6-C18芳基，C7-C18混合的(烷基-芳基)，C2-C12烷氧基羰基，C7-C18芳氧基羰基，C8-C18混合的(烷基-芳基)氧基羰基，腈，甲酰基，羧酸根，亚氨酸根，硫代羧酸根，等。优选的是，R18-R20各自独立地是氢或甲基。在一个实施方案中，丙烯酰基单体含有至少两个具有以上结构的丙烯酰基部分。在另一个实施方案中，丙烯酰基单体含有至少三个具有以上结构的丙烯酰基部分。
合适的丙烯酰基单体包括例如(甲基)丙烯酸甲酯，(甲基)丙烯酸乙酯，(甲基)丙烯酸异丙酯，(甲基)丙烯酸正丁酯，(甲基)丙烯酸异丁酯，(甲基)丙烯酸2-乙基己基酯，(甲基)丙烯酸2-羟乙酯，(甲基)丙烯酸3-羟丙酯，(甲基)丙烯酸羟丁基酯，(甲基)丙烯酸缩水甘油酯，(甲基)丙烯酸2，2-二甲基-3-羟丙酯，(甲基)丙烯酸异冰片酯，(甲基)丙烯酸四氢糠基酯，(甲基)丙烯酸3，4-环氧基环己基甲基酯，等；卤代(甲基)丙烯酸酯，例如(甲基)丙烯酸五溴苄基酯，等；和丙烯酸或甲基丙烯酸的酰胺，例如(甲基)丙烯酰胺，二丙酮(甲基)丙烯酰胺，N-(2-羟乙基)(甲基)丙烯酰胺，N-甲基(甲基)丙烯酰胺，N-乙基(甲基)丙烯酰胺，N，N-二甲基(甲基)丙烯酰胺，N，N-二甲基氨基丙基(甲基)丙烯酰胺，N，N-二甲基氨基丙基(甲基)丙烯酰胺，N，N-二甲基氨基乙基(甲基)丙烯酰胺，等；以及含有至少一种上述丙烯酰基单体的混合物。应该理解的是，前缀“(甲基)丙烯基”表示丙烯基或甲基丙烯基。其它合适的丙烯酰基单体描述在2001年1月18日递交的美国临时申请系列号60/262571中。
在一个实施方案中，除了丙烯酰基部分之外，丙烯酰基单体基本上不含其它可聚合的部分。
在优选的实施方案中，除了丙烯酰基部分之外，丙烯酰基单体基本上不含其它可聚合的部分。例如，在该实施方案中，丙烯酰基单体可以不含烯丙基部分或与芳环直接连接的乙烯基。
在所述组合物中，丙烯酰基单体的含量是至少约5重量份，优选至少约10重量份，基于每100重量份树脂计。在所述组合物中，聚亚芳基醚的含量是至多约60重量份，优选至多约50重量份，更优选至多约40重量份，基于每100重量份树脂计。
所述组合物进一步含有烯丙基单体。在这里，烯丙基单体定义为含有具有下面结构的烯丙基部分：
其中R21可以是氢、C1-C6烷基等。在优选的实施方案中，R21是氢。当烯丙基单体含有至少两个烯丙基部分时，它称为多官能烯丙基单体。
烯丙基单体可以包括例如烯丙基醇、烯丙基酯、烯丙基醚和烷氧基化烯丙基醇。烯丙基醇可以具有下面的通式结构：
其中R22是氢或C1-C6烷基。合适的烯丙基醇包括烯丙基醇、甲代烯丙基醇、2-乙基-2-丙烯-1-醇等，以及含有至少一种上述烯丙基醇的混合物。
烯丙基酯可以具有下面的通式结构：
其中R23是氢或C1-C6烷基，R24是氢，或饱和或不饱和的直链、支链或环状C1-C30烷基，芳基，烷基芳基，或芳烷基。合适的烯丙基酯包括例如甲酸烯丙酯、乙酸烯丙酯、丁酸烯丙酯、苯甲酸烯丙酯、乙酸甲代烯丙酯、烯丙基脂肪酯等，以及含有至少一种上述烯丙基酯的混合物。
烯丙基醚可以具有下面的通式结构：
其中R25是氢或C1-C6烷基，R26是饱和或不饱和的直链、支链或环状C1-C30烷基，芳基，烷基芳基，或芳烷基。合适的烯丙基醚包括例如烯丙基甲基醚、烯丙基乙基醚、烯丙基叔丁基醚、烯丙基甲基苄基醚等，以及含有至少一种上述烯丙基醚的混合物。
烯丙基单体还包括烷氧基化烯丙醇。烷氧基化烯丙醇可以具有下面的通式结构：
其中R27是氢或C1-C6烷基，A是氧基亚烷基，n是1至约50的值，它表示在烷氧基化烯丙醇中的氧基亚烷基的平均数目。氧基亚烷基可以包括氧基亚乙基、氧基亚丙基、氧基亚丁基，以及含有至少一种上述氧基亚烷基的混合物。烷氧基化烯丙醇可以通过烯丙醇与至多约50当量的一种或多种氧化烯在碱性催化剂存在下反应来制备，例如描述在美国专利3268561和4618703中。烷氧基化烯丙醇也可以通过酸解来制备，例如描述在Journal of the American Chemical Society，71卷，1152页起(1949)中。
在优选的实施方案中，烯丙基单体是多官能烯丙基单体。具体的多官能烯丙基单体包括例如己二酸二烯丙酯、柠康酸二烯丙酯、二甘醇酸二烯丙酯、二烯丙基醚、富马酸二烯丙酯、间苯二甲酸二烯丙酯、衣康酸二烯丙酯、马来酸二烯丙酯、邻苯二甲酸二烯丙酯、对苯二甲酸二烯丙酯、乌头酸三烯丙酯、氰脲酸三烯丙酯、异氰脲酸三烯丙酯、磷酸三烯丙酯、偏苯三酸三烯丙酯、邻-硅酸四烯丙酯等，以及含有至少一种上述烯丙基单体的混合物。
在优选的实施方案中，烯丙基单体基本上不含除了烯丙基部分之外的其它可聚合的部分。例如，在该实施方案中，烯丙基单体不含丙烯酰基单体或直接与芳环连接的乙烯基。
在所述组合物中，烯丙基单体的含量是至少约20重量份，优选至少约30重量份，更优选至少约40重量份，基于每100重量份树脂计。在所述组合物中，烯丙基单体的含量是至多约80重量份，优选至多约70重量份，更优选至多约65重量份，基于每100重量份树脂计。
所述组合物可以任选地进一步含有一种固化催化剂以便提高不饱和组分的固化速率。固化催化剂也称为引发剂，用于引发许多热塑性材料和热固性材料(包括不饱和聚酯、乙烯基酯、和烯丙基热固性材料)的聚合、固化或交联。固化催化剂的非限定性例子是描述在“Plastic Additives Handbook”，第4版，R.Gachter和H.Muller(编辑)，P.P.Klemchuck(助理编辑)，Hansen Publishers，纽约1993和授予Smith等人的美国专利5407972和授予Katayose等人的美国专利5218030中的那些。用于热固性材料的不饱和结构的固化催化剂包括任何能在高温下产生自由基的化合物。这些固化催化剂包括过氧型和非过氧型自由基引发剂。有用的过氧型引发剂包括例如过氧化苯甲酰、二枯基过氧化物、甲基乙基酮过氧化物、过氧化月桂酰、环己酮过氧化物、叔丁基氢过氧化物、叔丁基苯氢过氧化物、过辛酸叔丁酯、2，5-二甲基己烷-2，5-二氢过氧化物、2，5-二甲基-2，5-二(叔丁基过氧基)-己-3-炔、二叔丁基过氧化物、叔丁基枯基过氧化物、α，α’-双(叔丁基过氧基-间-异丙基)苯、2，5-二甲基-2，5-二(叔丁基过氧基)己烷、二枯基过氧化物、间苯二甲酸二(叔丁基过氧基)酯、叔丁基过氧基苯甲酸酯、2，2-双(叔丁基过氧基)丁烷、2，2-双(叔丁基过氧基)辛烷、2，5-二甲基-2，5-二(苯甲酰基过氧基)己烷、二(三甲基甲硅烷基)过氧化物、三甲基甲硅烷基苯基三苯基甲硅烷基过氧化物等，以及含有至少一种上述固化剂的混合物。典型的非过氧型引发剂包括例如2，3-二甲基-2，3-二苯基丁烷、2，3-三甲基甲硅烷氧基-2，3-二苯基丁烷等，以及含有至少一种上述固化剂的混合物。
本领域技术人员不需要多余的实验就能确定固化催化剂的适宜用量。固化催化剂的量可以是至少约0.1重量份，优选至少约1重量份，更优选至少约2重量份，基于每100重量份树脂计。固化催化剂的含量是至多约10重量份，优选至多约5重量份，基于每100重量份树脂计。优选选择固化催化剂的种类和用量，从而不会损害加工能力或保持粉末形式的可固化配料。
除了上述组分之外，可固化树脂组合物可以进一步含有选自下列的添加剂：阻燃剂、阻燃增效剂、脱模剂和其它润滑剂、抗氧化剂、热稳定剂、紫外线稳定剂、颜料、染料、着色剂、抗静电剂、纤维增强剂、盘形填料、低纵横比的填料、合成树脂、天然树脂、热塑性弹性体等，以及含有至少一种上述添加剂的混合物。本领域技术人员不需要多余的实验就能确定这些添加剂的适宜用量。添加剂的非限定性例子是描述在“Plastic Additives Handbook”，第4版，R.Gachter和H.Muller(编辑)，P.P.Klemchuck(助理编辑)，HansenPublishers，纽约1993中的那些。许多具体的添加剂也描述在美国专利临时申请系列号60/262571(2001年1月18日递交)中。
所述组合物可以进一步含有一种或多种填料，包括低纵横比的填料、纤维填料和高分子填料。这些本领域已知的填料的例子包括描述在“Plastic Additives Handbook”，第4版，R.Gachter和H.Muller(编辑)，P.P.Klemchuck(助理编辑)，Hansen Publishers，纽约1993中的那些。填料的非限定性例子包括二氧化硅粉末，例如熔凝二氧化硅、结晶二氧化硅、天然硅砂，和各种被硅烷涂布的二氧化硅；硼氮化物粉末和硼硅酸盐粉末；氧化铝和氧化镁(或氧化镁)；硅灰石，包括经过表面处理的硅灰石；硫酸钙(例如是其酸酐、二水合物或三水合物的形式)；碳酸钙，包括白垩、石灰石、大理石和合成的沉淀碳酸钙，通常是研磨颗粒的形式，常含有98+％的CaCO3，其余的是其它无机化合物，例如碳酸镁、氧化铁和硅铝酸盐；经过表面处理的碳酸钙；滑石，包括纤维状、组合状(modular)、针形和片状的滑石；玻璃球，是空心的和实心的，以及经过表面处理的玻璃球，它通常含有偶联剂例如硅烷偶联剂和/或含有导电涂料；高岭土，包括硬的、软的、煅烧的高岭土，以及含有各种本领域已知的涂料以促进分散在热固性树脂中并与其相容的那些高岭土；云母，包括金属化云母，和用氨基硅烷或丙烯酰基硅烷涂料进行表面处理从而赋予配混共混物以良好物理性能的那些云母；长石和霞石正长岩；硅酸盐球；烟灰；煤胞；fillite；硅铝酸盐(无定形)，包括硅烷化的和金属化的硅铝酸盐；石英；石英岩；珍珠岩；硅藻土(Tripoli)；硅藻土；碳化硅；硫化钼；硫化锌；硅酸铝(富铝红柱石)；合成硅酸钙；硅酸锆；钛酸钡；铁酸钡；硫酸钡和重晶石；颗粒或纤维状的铝、青铜、锌、铜和镍；炭黑，包括导电炭黑；石墨，例如石墨粉末；片状填料和增强剂例如玻璃片、片状碳化硅、二硼化铝、铝片和钢片；加工的无机填料，例如由含有硅酸铝、氧化铝、氧化镁和硫酸钙七水合物中的至少一种物质的共混物获得的那些；天然纤维，包括木粉、纤维素、棉、剑麻、黄麻、淀粉、软木粉、木质素、花生壳、玉米、谷粒壳；合成增强纤维，包括聚酯纤维，例如聚对苯二甲酸乙二酯纤维、聚乙烯醇纤维、芳族聚酰胺纤维、聚苯并咪唑纤维、聚酰亚胺纤维、聚苯硫醚纤维、聚醚醚酮纤维、硼纤维、陶瓷纤维，例如碳化硅，由铝、硼和硅的混合氧化物获得的纤维；单晶纤维或“针状单晶”包括碳化硅纤维、氧化铝纤维、碳化硼纤维、铁纤维、镍纤维、铜纤维；玻璃纤维，包括织造玻璃纤维，例如E、A、C、ECR、R、S、D和NE玻璃，以及石英；蒸汽生长型碳纤维，包括平均直径为约3.5-约500nm的那些，描述在例如授予Tibbetts等人的美国专利4565684和5024818，授予Arakawa的美国专利4572813，授予Tennent的美国专利4663230和5165909，授予Komatsu等人的美国专利4816289，授予Arakawa的美国专利4876078，授予Tennent的美国专利5589152，授予Nahass等人的美国专利5591382中；以及含有至少一种上述填料的混合物等。
上述填料可以与各种涂料一起使用，包括例如金属涂料和硅烷涂料，以便改进与热固性共混物的相容性和粘合性。
对在所述组合物中填料的含量没有特殊的限制，填料量将取决于该组合物的最终用途。当存在填料时，填料的用量通常是至多约2000重量份，优选至多约1500重量份，更优选至多约1000重量份，基于每100重量份树脂总量计。填料量通常是至少约1重量份，优选至少约10重量份，更优选至少约20重量份，基于每100重量份树脂总量计。
在一个实施方案中，该组合物基本上不含链烯基芳族单体，其中链烯基取代基直接与芳环连接。“基本上不含链烯基芳族单体”表示这种单体不是有意添加的。这些链烯基芳族单体包括例如苯乙烯、二乙烯基苯和乙烯基吡啶。
虽然组合物定义为含有多种组分，但是应该理解的是各组分在化学上是不同的，特别是在单个化合物可以满足对一种以上组分的定义的情况下。
所述组合物的一个优点是其能以粉末的形式配制。对于一些应用，优选粉末基本上不含任何尺寸大于约300微米的颗粒，优选基本上不含任何尺寸大于约150微米的颗粒，更优选基本上不含任何尺寸大于约100微米的颗粒，进一步更优选基本上不含任何尺寸大于约50微米的颗粒。“基本上不含”表示所述组合物包含少于5重量％、优选少于2重量％、更优选少于1重量％的具有特定尺寸的颗粒。在一个实施方案中，所述组合物可以以含有可固化树脂颗粒和磨料颗粒的混合物形式来配制，其中对粒度的上述限制仅仅适用于可固化树脂颗粒。
为了促进在环境条件下的处理，可以优选该组合物的熔点是至少约50℃，优选至少约60℃，更优选至少约70℃。为了保证在低于典型模塑温度下熔融，可以优选该组合物的熔点是至多约150℃，优选至多约140℃，更优选至多约130℃。
在一个实施方案中，所述组合物含有约10-约50重量份的聚亚芳基醚；约5-约60重量份的丙烯酰基单体；和约20-约80重量份的烯丙基单体；其中所有重量份都基于100重量份树脂计；和其中该组合物是粉末。
在另一个实施方案中，所述组合物含有约15-约45重量份的封端聚亚芳基醚；约10-约40重量份的多官能丙烯酰基单体；和约30-约70重量份的多官能烯丙基单体；其中所有重量份都基于100重量份树脂计；和其中该组合物是粉末。
在另一个实施方案中，所述组合物含有约25-约35重量份的封端聚(2，6-二甲基-1，4-亚苯基醚)；约10-约20重量份的三羟甲基丙烷三丙烯酸酯或三羟甲基丙烷三甲基丙烯酸酯；和约50-约60重量份的邻苯二甲酸二烯丙酯；其中所有重量份都基于100重量份树脂计；和其中该组合物是粉末。
应该理解的是，本发明包括任何上述可固化树脂的反应产物，以及含有固化后的组合物的制品。
固化后的树脂组合物的一个优点是韧性得到改进。这可以例如表现在按照ASTM D5045检测的断裂韧性(KIC)至少为约0.9Mpa-m1/2，优选至少为约1.0Mpa-m1/2，更优选至少为约1.1Mpa-m1/2，进一步更优选至少为约1.2Mpa-m1/2。
用于加工所述组合物的方法包括铸塑，包括例如离心和静态铸塑；接触模塑，包括筒式接触模塑；压模；层压，包括湿式和干式铺置以及喷雾铺置；树脂转移模塑，包括真空辅助的树脂转移模塑和化学辅助的树脂转移模塑；SCRIMP加工；挤出；成型为高强度复合材料；开放模塑或连续组合树脂和玻璃；丝缠绕，包括筒式丝缠绕等，以及含有至少一种上述方法的组合。其它方法已经描述在“Polyesters andTheir Applications”，Bjorksten Research Laboratories，JohanBjorksten(pres)，Henry Tovey(Ch.Lit.Ass.)，BettyHarker(Ad.Ass)，James Henning(Ad.Ass)，Reinhold PublishingCorporation，纽约，1956，“Use of Epoxy Resins”，W.G.Potter，Newnes-Buttersworth，伦敦1975，“Chemistry and Technology ofCyanate Ester Resins”，I.Hamerton，Blakie Academic Publishingan Imprint of Chapman Hall。粉状树脂组合物用于与其它粉状添加剂混合，形成干混物，因为这种共混比在树脂组合物为粘性液体或糊料情况下更容易进行。当添加剂部分构成共混物的大部分、例如占组合物总量的约70-约80重量％和其余的是可固化树脂时，粉状树脂组合物的使用是特别有利的。
在一个实施方案中，所述组合物可以通过这样的方法制备：将聚亚芳基醚和烯丙基单体共混形成第一紧密共混物；将第一紧密共混物与丙烯酰基单体共混，形成第二紧密共混物；并加工第二紧密共混物，形成可固化的粉末。加工第二紧密共混物形成可固化粉末的操作可以优选包括将第二紧密共混物在最多约-75℃、优选最多约-150℃、更优选最多约-170℃、进一步更优选最多约-190℃的温度下研磨。这些温度使树脂发脆，从而促进研磨成小颗粒。例如，树脂可以通过浸入液氮中并冷却至-196℃而被低温研磨；然后可以以分份方式将其快速转移到研磨机的开口中，在那里与所需筛目的旋转筛接触，经过筛网到达收集库。进行低温研磨的装置是例如Retsch/Brinkmann的ZM-1研磨机。该方法进一步包括将可固化粉末与固化催化剂共混。
在另一个实施方案中，所述组合物可以通过这样的方法制备：将约20-约80重量份的烯丙基单体和约10-约50重量份的聚亚芳基醚共混形成第一紧密共混物；将第一紧密共混物与约5-约60重量份的丙烯酰基单体共混，形成第二紧密共混物；在低于约-75℃的温度下研磨第二紧密共混物，形成第一可固化粉末；将该第一粉末与固化催化剂共混，形成第二可固化粉末。
对固化所述混合物的方法没有特殊的限制。所述组合物可以例如通过热固化或使用辐射固化技术、包括UV辐射和电子束辐射来固化。
下面将通过非限定性实施例进一步说明本发明。
实施例1
在玻璃反应器中将邻苯二甲酸二烯丙酯(510g，从Aldrich获得，是纯度为97％的液体)加热到160-165℃。向其中加入甲基丙烯酸酯封端的聚(2，6-二甲基-1，4-亚苯基醚)(340g)，它在25℃氯仿中的特性粘数是0.25dL/g。使用1999年11月16日递交的美国专利申请系列号09/440747中描述的工序，使相应的未封端的聚亚芳基醚与甲基丙烯酸酐反应，从而制备封端的聚亚芳基醚。该混合物进行搅拌并加热直到聚亚芳基醚完全溶解。然后向反应烧瓶中加入三羟甲基丙烷三甲基丙烯酸酯(150g，从Sartomer获得，是纯液体)，并混合直到完全共混。然后将该溶液倒入平型容器中，使其冷却，从而形成硬化的蜡状物质。将该树脂混合物在液氮中冷却到-196℃，并快速转移到Retsch/Brinkmann的ZM-1研磨机中，在那里研磨，制得粒度小于50粒度的粉末树脂。向该粉末树脂中加入占树脂共混物总量的2重量％的引发剂二枯基过氧化物。
采用本领域技术人员已知的方法，将一部分粉末树脂于150℃和约200磅/平方英寸(psi)的压力下压模10分钟。样品是公称尺寸为3英寸直径和0.125英寸厚度的实心透明盘。
按照上述工序制得的各种样品进一步于150-160℃固化2小时。使用Barcol实验机(ASTM D2583)检测几个样品的硬度，得到约30-40的Barcol硬度值。硬度也可以通过将钝探针的尖端压入表面来定性地检测。在表面上没有观察到凹痕。韧性通过使样品经受人手弯曲力(没有出现明显的弯曲)和用20盎司锤冲击样品(样品不会断裂)来定性地检测。
采用本领域技术人员已知的方法，将一部分粉末树脂于140℃下压模5分钟。所得的样品是公称尺寸为2.5英寸直径和0.125英寸厚度的实心透明盘，无孔、无裂纹，基本上是硬且韧的。相似地制备八个重复样品。将九个样品中的五个于165℃固化1小时。为了对比，从Dow Chemical Company的商品名DERAKANEM311-450的乙烯基酯树脂模塑相似的样品。在将样品加工成合适的尺寸和缺口后，按照ASTMD5045检测断裂韧性，并在缺口处引发裂纹。断裂韧性由平均±标准偏差表示，列在下表中。结果显示，与商购乙烯基酯树脂相比，固化后的树脂组合物显示改进的韧性。
表
| 树脂类型 | 是否后固化 | K1C(Mpa-m<sup>1/2</sup>) |
| 本实施例 | 否 | 1.28±0.12 |
| 本实施例 | 是 | 1.14±0.05 |
| DERAKANEM311-450 | 否 | 0.82±0.12 |
实施例2
重复实施例1的工序，改变邻苯二甲酸二烯丙酯(600g)、甲基丙烯酸酯封端的聚(2，6-二甲基-1，4-亚苯基醚)(250g)和三羟甲基丙烷三甲基丙烯酸酯(150g)的量。压模得到的样品是公称尺寸为3英寸直径和0.125英寸厚度的实心透明盘。在固化后，如实施例1所述进行硬度和韧性实验，显示模塑制品是硬且韧的。
实施例3
重复实施例1的工序，改变邻苯二甲酸二烯丙酯(550g)、甲基丙烯酸酯封端的聚(2，6-二甲基-1，4-亚苯基醚)(300g)和三羟甲基丙烷三甲基丙烯酸酯(150g)的量。在该实施例中，甲基丙烯酸酯封端的聚(2，6-二甲基-1，4-亚苯基醚)具有0.30dL/g的特性粘数，并使用与制备特性粘数0.25dL/g的物质相同的方法制备。压模得到的样品是公称尺寸为3英寸直径和0.125英寸厚度的实心透明盘，并基本上是硬且韧的。在固化后，如实施例1所述进行硬度和韧性实验，显示模塑制品是硬且韧的。
实施例4
将9g如实施例1所述的粉末树脂与粒度尺寸为500的10g碳化硅粉末和粒度尺寸为150的31g碳化硅粉末干混。然后采用本领域技术人员已知的方法，将该树脂/磨料共混物于155℃和约2000psi的压力下压模15分钟。所得的样品是公称尺寸为3英寸直径和0.125英寸厚度的实心透明盘，并基本上是硬且韧的。使用相同的树脂/磨料共混物再模塑两个样品，各自是基本上是硬且韧的材料。在进一步固化后，如实施例1所述进行硬度和韧性实验，显示模塑制品是硬且韧的。
应该注意的是，树脂复合材料的化学组分使得能在不产生挥发物的情况下固化。此优点不适用于酚树脂，因为酚树脂的固化会产生挥发性产品，在固化的树脂中产生多孔结构，这损害了其物理性能。
虽然已经参考优选实施方案描述了本发明，但本领域技术人员应该理解的是在不偏离本发明主旨的范围内可以进行各种变化。另外，在不偏离本发明主旨的范围内可以在本发明教导中应用许多特定条件或材料。所以，本发明并不限于这些优选实施方案，但本发明包括落在所附权利要求范围内的所有实施方案。
所有引用的专利和其它文献在此全文引作参考。
Claims (10)
1.一种可固化树脂组合物，它含有：
10-50重量份的聚亚芳基醚；
5-60重量份的丙烯酰基单体；其中丙烯酰基单体含有至少一个具有下面结构的丙烯酰基部分：
其中R18-R20各自独立地选自氢，C1-C12烷基，C2-C12链烯基，C6-C18芳基，C7-C18混合的(烷基-芳基)，C2-C12烷氧基羰基，C7-C18芳氧基羰基，C8-C18混合的(烷基-芳基)氧基羰基，腈，甲酰基，羧酸根，亚氨酸根和硫代羧酸根；
20-80重量份的烯丙基单体，其中烯丙基单体含有具有下面结构的烯丙基部分：
其中R21选自氢和C1-C6烷基；
其中所述可固化树脂组合物是粉末，且所述所有重量份都是基于100重量份树脂计。
2.权利要求1的可固化树脂组合物，其中聚亚芳基醚包含多个下式的结构单元：
其中对于每个结构单元，每个Q1独立地是卤素、伯或仲C1-C12烷基、苯基、C1-C12卤代烷基、C1-C12氨基烷基、C1-C12烃氧基、或C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子；和每个Q2独立地是氢、卤素、伯或仲C1-C12烷基、苯基、C1-C12卤代烷基、C1-C12氨基烷基、C1-C12烃氧基、或C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子。
3.权利要求1的可固化树脂组合物，其中丙烯酰基单体含有至少一个具有以下结构的丙烯酰基部分：
其中R16和R17各自独立地选自氢和C1-C12烷基，其中R16和R17可以位于碳-碳双键的顺式或反式位置。
4.权利要求1的可固化树脂组合物，其进一步含有固化催化剂。
5.权利要求1的可固化树脂组合物，其进一步含有填料。
6.权利要求1的可固化树脂组合物，其中聚亚芳基醚包括具有下面结构的封端聚亚芳基醚：
Q-(J-K)y，
其中Q是一元、二元或多元酚的残基；y是1-100；J包含具有下面结构的重复单元：
其中R1-R4各自独立地选自氢、卤素、伯或仲C1-C12烷基、C2-C12链烯基、C2-C12炔基、C1-C12氨基烷基、C1-C12羟烷基、苯基、C1-C12卤代烷基、C1-C12烃氧基和C2-C12卤代烃氧基，其中至少两个碳原子隔开卤原子和氧原子；m是1至200；和K是选自以下的封端基团：
-Y-R5，
和
其中R5是C1-C12烷基；R6-R8各自独立地选自氢、C1-C12烷基、C2-C12链烯基、C6-C18芳基、C7-C18混合的(烷基-芳基)、C2-C12烷氧基羰基、C7-C12芳氧基羰基、C8-C18混合的(烷基-芳基)氧基羰基、腈、甲酰基、羧酸根、亚氨酸根、硫代羧酸根；R9-R13各自独立地选自氢、卤素、C1-C12烷基、羟基和氨基；和其中Y具有选自以下结构的二价基团：
其中R14和R15各自独立地选自氢和C1-C12烷基。
7.权利要求1的可固化树脂组合物，其中丙烯酰基单体选自三羟甲基丙烷三甲基丙烯酸酯、三羟甲基丙烷三丙烯酸酯、1，6-己二醇二甲基丙烯酸酯、1，6-己二醇二丙烯酸酯、乙二醇二甲基丙烯酸酯、乙二醇二丙烯酸酯、丙二醇二甲基丙烯酸酯、丙二醇二丙烯酸酯、环己烷二甲醇二甲基丙烯酸酯、环己烷二甲醇二丙烯酸酯、丁二醇二甲基丙烯酸酯、丁二醇二丙烯酸酯、二甘醇二甲基丙烯酸酯、二甘醇二丙烯酸酯、三甘醇二甲基丙烯酸酯、三甘醇二丙烯酸酯、甲基丙烯酸异冰片酯、丙烯酸异冰片酯、甲基丙烯酸甲酯、丙烯酸甲酯，以及含有至少一种上述丙烯酰基单体的混合物。
8.一种固化的树脂组合物，它含有可固化树脂组合物的反应产物，所述可固化树脂组合物含有：
10-50重量份的聚亚芳基醚；
5-60重量份的丙烯酰基单体，其中丙烯酰基单体含有至少一个具有下面结构的丙烯酰基部分：
其中R18-R20各自独立地选自氢，C1-C12烷基，C2-C12链烯基，C6-C18芳基，C7-C18混合的(烷基-芳基)，C2-C12烷氧基羰基，C7-C18芳氧基羰基，C8-C18混合的(烷基-芳基)氧基羰基，腈，甲酰基，羧酸根，亚氨酸根和硫代羧酸根；和
20-80重量份的烯丙基单体，其中烯丙基单体含有具有下面结构的烯丙基部分：
其中R21选自氢和C1-C6烷基；；
其中所述可固化树脂组合物是粉末，且所述固化的树脂组合物是可固化的树脂组合物的固化的产品，且所述所有重量份都是基于100重量份树脂计。
9.一种形成可固化树脂组合物的方法，包括：
使10-50重量份聚亚芳基醚和20-80重量份烯丙基单体共混以形成第一共混物；
使第一共混物与5-60重量份丙烯酰基单体共混，以形成第二共混物；和
加工第二共混物，以形成粉末形式的可固化树脂组合物，
其中丙烯酰基单体含有至少一个具有下面结构的丙烯酰基部分：
其中R18-R20各自独立地选自氢，C1-C12烷基，C2-C12链烯基，C6-C18芳基，C7-C18混合的(烷基-芳基)，C2-C12烷氧基羰基，C7-C18芳氧基羰基，C8-C18混合的(烷基-芳基)氧基羰基，腈，甲酰基，羧酸根，亚氨酸根和硫代羧酸根；
烯丙基单体含有具有下面结构的烯丙基部分：
其中R21选自氢和C1-C6烷基；
其中所有重量份都基于100重量份树脂计。
10.权利要求9的方法，其中
在低于-75℃的温度下研磨第二共混物，以形成粉末形式的可固化树脂组合物以及
使该可固化树脂组合物粉末与固化催化剂共混。
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Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002536778A (ja) | 1999-02-12 | 2002-10-29 | ゼネラル・エレクトリック・カンパニイ | データ記憶媒体 |
| US7179551B2 (en) * | 1999-02-12 | 2007-02-20 | General Electric Company | Poly(arylene ether) data storage media |
| US7235192B2 (en) * | 1999-12-01 | 2007-06-26 | General Electric Company | Capped poly(arylene ether) composition and method |
| US6812276B2 (en) * | 1999-12-01 | 2004-11-02 | General Electric Company | Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom |
| US6905637B2 (en) * | 2001-01-18 | 2005-06-14 | General Electric Company | Electrically conductive thermoset composition, method for the preparation thereof, and articles derived therefrom |
| US6897282B2 (en) * | 2000-07-10 | 2005-05-24 | General Electric | Compositions comprising functionalized polyphenylene ether resins |
| US6384176B1 (en) * | 2000-07-10 | 2002-05-07 | General Electric Co. | Composition and process for the manufacture of functionalized polyphenylene ether resins |
| AU2003300377B2 (en) * | 2002-10-11 | 2009-04-02 | University Of Connecticut | Blends of amorphous and semicrystalline polymers having shape memory properties |
| CN100441637C (zh) * | 2002-12-20 | 2008-12-10 | 通用电气公司 | 热固性复合材料组合物、方法及产品 |
| US7250477B2 (en) * | 2002-12-20 | 2007-07-31 | General Electric Company | Thermoset composite composition, method, and article |
| US7226980B2 (en) | 2003-08-07 | 2007-06-05 | General Electric Company | Thermoset composition, method for the preparation thereof, and articles prepared therefrom |
| US7211639B2 (en) * | 2003-10-03 | 2007-05-01 | General Electric Company | Composition comprising functionalized poly(arylene ether) and ethylene-alkyl (meth)acrylate copolymer, method for the preparation thereof, and articles prepared therefrom |
| US7067595B2 (en) * | 2003-10-03 | 2006-06-27 | General Electric Company | Poly (arylene ether) composition and method |
| US7101923B2 (en) | 2003-10-03 | 2006-09-05 | General Electric Company | Flame-retardant thermoset composition, method, and article |
| US7148296B2 (en) * | 2003-10-03 | 2006-12-12 | General Electric Company | Capped poly(arylene ether) composition and process |
| US7329708B2 (en) * | 2004-08-18 | 2008-02-12 | General Electric Company | Functionalized poly(arylene ether) composition and method |
| US20060135704A1 (en) * | 2004-12-22 | 2006-06-22 | Vallance Michael A | Tack free compositions useful for electronic encapsulation |
| US20070066710A1 (en) * | 2005-09-21 | 2007-03-22 | Peters Edward N | Method for electrical insulation and insulated electrical conductor |
| US7541421B2 (en) * | 2005-12-08 | 2009-06-02 | Sabic Innovative Plastics Ip B.V. | Poly(arylene ether) copolymer |
| JP2007177113A (ja) * | 2005-12-28 | 2007-07-12 | Teijin Techno Products Ltd | 有機高分子重合体微粒子およびその製造方法 |
| WO2008063709A2 (en) * | 2006-06-20 | 2008-05-29 | Polyone Corporation | Thermally conductive polymer compounds containing zinc sulfide |
| US20080015104A1 (en) * | 2006-07-13 | 2008-01-17 | Unimin Corporation | Ultrafine nepheline syenite |
| US8858699B2 (en) * | 2006-07-13 | 2014-10-14 | Unimin Corporation | Ultra fine nepheline syenite powder and products for using same |
| US20080040980A1 (en) * | 2006-07-13 | 2008-02-21 | Unimin Corporation | Method of processing nepheline syenite |
| US20080071034A1 (en) * | 2006-09-15 | 2008-03-20 | Christina Louise Braidwood | Poly(arylene ether) composition and method |
| US20080097027A1 (en) * | 2006-10-23 | 2008-04-24 | General Electric Company | Varnish composition for insulating electrical machinery |
| US7757976B2 (en) * | 2007-02-07 | 2010-07-20 | Unimin Corporation | Method of processing nepheline syenite powder to produce an ultra-fine grain size product |
| WO2009008965A1 (en) * | 2007-07-09 | 2009-01-15 | Unimin Corporation | Nepheline syenite powder with controlled particle size and novel method of making same |
| BRPI0822390B1 (pt) * | 2008-04-17 | 2018-06-26 | Unimin Corporation | Pó ultrafino formado a partir de mineral ou material de rocha com distribuição de tamanho de partícula controlada para filmes térmicos ou revestimentos, e seu método de produção |
| DE212013000085U1 (de) | 2012-03-20 | 2014-11-05 | Unimin Corporation | Mineralische Füllmittel zur Verwendung als Ersatz für Holzfüllmittel in Holzimitatprodukten und diese enthaltende Holzimitatprodukte |
| CN104119780B (zh) * | 2013-04-26 | 2017-03-15 | 比亚迪股份有限公司 | 一种可金属化组合物及其制备方法、非金属表面选择性金属化方法 |
| US9493610B2 (en) | 2013-06-03 | 2016-11-15 | Polyone Corporation | Low molecular weight polyphenylene ether prepared without solvents |
| US20150105505A1 (en) * | 2013-10-11 | 2015-04-16 | Isola Usa Corp. | Varnishes and Prepregs and Laminates Made Therefrom |
| EP3034551A1 (en) * | 2014-12-17 | 2016-06-22 | Akzo Nobel Chemicals International B.V. | Powder mixture comprising organic peroxide |
| EP3283555B1 (de) * | 2015-04-14 | 2019-12-04 | Basf Se | Verfahren zur zähmodifizierung von duroplasten |
| WO2017091569A1 (en) * | 2015-11-25 | 2017-06-01 | Sabic Global Technologies B.V. | Poly(phenylene ether)-containing composite and laminate prepared therefrom, and method of forming composite |
| US11686106B2 (en) * | 2020-07-22 | 2023-06-27 | Kevin Reynolds | Drywall finishing system |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3597216A (en) * | 1969-09-24 | 1971-08-03 | Celanese Corp | High temperature photoresist of cross-linked poly(2,6-dimethyl-1,4-phenylene oxide) |
| CN1064088A (zh) * | 1991-01-11 | 1992-09-02 | 旭化成工业株式会社 | 可固化的聚苯氧树脂组合物及由此可获得的已固化树脂组合物 |
| JPH0812875A (ja) * | 1994-06-29 | 1996-01-16 | Matsushita Electric Works Ltd | ポリフェニレンオキサイド系成形材料の製造方法 |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3219625A (en) * | 1961-05-29 | 1965-11-23 | Gen Electric | Process for oxidizing phenols to polyphenyl ethers and diphenoquinones |
| BE635350A (zh) * | 1962-07-24 | |||
| US3268561A (en) * | 1963-12-24 | 1966-08-23 | Jefferson Chem Co Inc | Glycidyl ethers |
| US3375228A (en) * | 1967-05-10 | 1968-03-26 | Gen Electric | Hot capping of polyphenylene ethers |
| US3557045A (en) * | 1967-11-13 | 1971-01-19 | Fmc Corp | Mixed thermosetting resin compositions containing polyphenylene ethers |
| NL141215B (nl) * | 1968-01-23 | 1974-02-15 | Fmc Corp | Werkwijze voor het bereiden van thermohardende harsmaterialen. |
| CA927032A (en) * | 1969-06-30 | 1973-05-22 | H. Beacham Harry | Flame-retardant resin compositions |
| US3883612A (en) * | 1971-06-07 | 1975-05-13 | Scm Corp | Low-shrink thermosetting polymers |
| US4028341A (en) * | 1974-02-11 | 1977-06-07 | General Electric Company | Process for the preparation of polyphenylene oxides with hydrolytically stable copper catalysts |
| US4048143A (en) * | 1974-02-11 | 1977-09-13 | General Electric Company | Process for capping polyphenylene oxide |
| US4092294A (en) * | 1976-08-30 | 1978-05-30 | General Electric Company | Method for preparing polyphenylene ethers |
| US4165422A (en) * | 1977-05-26 | 1979-08-21 | General Electric Company | Acyl capped quinone-coupled polyphenylene oxides |
| US4148843A (en) * | 1977-12-23 | 1979-04-10 | General Electric Company | Compositions of capped polyphenylene oxides and alkenyl aromatic resins |
| US4327013A (en) * | 1979-05-01 | 1982-04-27 | Union Carbide Corporation | Poly(acrylate) containing compositions and process for producing molded articles |
| DE3117514A1 (de) | 1981-05-02 | 1982-12-02 | Basf Ag, 6700 Ludwigshafen | Aromatische polyether mit olefinischen endgruppen |
| USH521H (en) * | 1982-06-30 | 1988-09-06 | Thermosetting polysulfones | |
| DE3224691A1 (de) * | 1982-07-02 | 1984-01-05 | Chemische Werke Hüls AG, 4370 Marl | Verfahren zur herstellung von hochmolekularen polyphenylenoxiden |
| EP0135124A3 (en) | 1983-08-23 | 1986-11-20 | General Electric Company | Crosslinkable flame retardant composition of polyphenylene ether and elastomers |
| US4572813A (en) * | 1983-09-06 | 1986-02-25 | Nikkiso Co., Ltd. | Process for preparing fine carbon fibers in a gaseous phase reaction |
| DE3340493A1 (de) * | 1983-11-09 | 1985-05-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von bifunktionellen polyphenylenoxiden |
| US4562243A (en) * | 1984-03-06 | 1985-12-31 | The B. F. Goodrich Company | Crosslinkable difunctionalized polyarylene polyethers |
| US4663402A (en) * | 1984-03-06 | 1987-05-05 | The B. F. Goodrich Company | Non-catalytic process for the preparation of difunctionalized polyarylene polyethers |
| US5091480A (en) * | 1984-03-06 | 1992-02-25 | The B. F. Goodrich Company | Comb-like polymers and graft copolymers from polyarylene polyether macromonomers |
| US4701514A (en) * | 1984-03-06 | 1987-10-20 | B.F. Goodrich Company | Difunctionalized polyarylene polyethers and process for preparation thereof |
| US4665137A (en) * | 1984-03-06 | 1987-05-12 | The B. F. Goodrich Company | Crosslinkable difunctionalized poly(phenylene oxide) and process for preparation thereof |
| JPS60224816A (ja) * | 1984-04-20 | 1985-11-09 | Nikkiso Co Ltd | 気相成長による炭素繊維の製造方法 |
| US4816289A (en) * | 1984-04-25 | 1989-03-28 | Asahi Kasei Kogyo Kabushiki Kaisha | Process for production of a carbon filament |
| US4565684A (en) * | 1984-08-20 | 1986-01-21 | General Motors Corporation | Regulation of pyrolysis methane concentration in the manufacture of graphite fibers |
| US4634742A (en) * | 1984-11-08 | 1987-01-06 | The B. F. Goodrich Company | Polyarylene polyethers with pendant vinyl groups and process for preparation thereof |
| US4806601A (en) * | 1984-11-08 | 1989-02-21 | The B. F. Goodrich Company | Polyarylene polyethers with pendant vinyl and ethynyl groups and process for preparation thereof |
| US5165909A (en) * | 1984-12-06 | 1992-11-24 | Hyperion Catalysis Int'l., Inc. | Carbon fibrils and method for producing same |
| US4663230A (en) * | 1984-12-06 | 1987-05-05 | Hyperion Catalysis International, Inc. | Carbon fibrils, method for producing same and compositions containing same |
| US4604417A (en) * | 1984-12-10 | 1986-08-05 | The Goodyear Tire & Rubber Company | Polymerizable thioester synergists |
| CA1285675C (en) * | 1985-03-25 | 1991-07-02 | Takaaki Sakamoto | Method of preparing polyphenylene oxide composition and laminate using the composition |
| EP0206072B2 (en) | 1985-06-17 | 1998-07-01 | Ppg Industries, Inc. | A method of preparation of acrylic polymer |
| NL8502116A (nl) * | 1985-07-24 | 1987-02-16 | Gen Electric | Werkwijze voor het bereiden van een polymeermengsel, dat een polyfenyleen ether en een polyamide bevat. |
| US4618703A (en) * | 1985-09-13 | 1986-10-21 | Atlantic Richfield Company | Production of the acrylates and methacrylates of oxyalkylated allyl alcohol |
| US4871816A (en) * | 1986-03-10 | 1989-10-03 | The B.F. Goodrich Company | Triblock polyarylene polyether with polysiloxane segment and impact-improved blends thereof |
| DE3774521D1 (de) | 1986-09-22 | 1991-12-19 | Gen Electric | Haertbare zusammensetzungen von gehaerteten polyphenylenaethern, die polymere mit sich gegenseitig durchdringenden strukturen enthalten, und verfahren. |
| DE3706561A1 (de) * | 1987-02-28 | 1988-09-08 | Basf Ag | Lichtempfindliches aufzeichnungsmaterial mit erhoehter flexibilitaet |
| US4760118A (en) * | 1987-03-23 | 1988-07-26 | General Electric Company | Polyphenylene ether capped with salicylic acid ester |
| US4816515A (en) * | 1987-04-13 | 1989-03-28 | General Electric Company | Impact modified polyphenylene ether interpolymer resins |
| CA1336526C (en) * | 1987-09-09 | 1995-08-01 | Hiroji Oda | Cured polyphenylene ether resin and a curable polyphenylene ether resin |
| ATE100478T1 (de) * | 1987-11-05 | 1994-02-15 | Kureha Chemical Ind Co Ltd | Polymerlegierung aus polyarylenpolyaether und verfahren zu deren herstellung. |
| DE3813355A1 (de) * | 1988-04-21 | 1989-11-02 | Huels Chemische Werke Ag | Funktionalisierte polyphenylenether und verfahren zu ihrer herstellung |
| KR0147376B1 (ko) * | 1988-07-07 | 1998-08-17 | 오노 알버어스 | 개질된 폴리페닐렌 에테르의 제조 방법 및 비닐 치환 방향족의 개질된 고온 경질 중합체 내에서의 이의 사용 방법 |
| US5219951A (en) * | 1988-07-07 | 1993-06-15 | Shell Internationale Research Maatschappij B.V. | Process for preparation of modified polyphenylene ether or related polymers and the use thereof in modified high temperature rigid polymer of vinyl substituted aromatics |
| US5218030A (en) * | 1989-02-08 | 1993-06-08 | Asahi Kasei Kogyo Kabushiki Kaisha | Curable polyphenylene ether resin composition and a cured resin composition obtainable therefrom |
| US5213886A (en) * | 1989-02-17 | 1993-05-25 | General Electric Company | Curable dielectric polyphenylene ether-polyepoxide compositions |
| NL8900497A (nl) | 1989-03-01 | 1990-10-01 | Gen Electric | Werkwijze voor het bereiden van korrels polyfenyleentherpolystyreen, gevormde korrels. |
| US5118748A (en) * | 1989-03-07 | 1992-06-02 | Mitsubishi Cable Industries Ltd. | Phenylene oxide polymer composition |
| CA2013041A1 (en) * | 1989-04-07 | 1990-10-07 | Johannes M. Zijderveld | Process for preparation of modified polyphenylene ether or related polymers and the use thereof in modified high temperature rigid polymer of vinyl substituted aromatics |
| US5171761A (en) * | 1989-06-02 | 1992-12-15 | Enichem S.P.A. | Cross-linkable compositions based on polyphenylene ethers and unsaturated monomers copolymerizable radically |
| GB8913542D0 (en) * | 1989-06-13 | 1989-08-02 | Shell Int Research | Process for modification of polyphenylene ether or related polymers with a cyclic anhydride and the use thereof in modified,high temperature rigid polymer |
| US5079268A (en) * | 1989-06-23 | 1992-01-07 | Shell Research Limited | Poly(alkenyl substituted aromatic) and elastomer containing polymer compositions and process for their preparation |
| NL8902092A (nl) | 1989-08-18 | 1991-03-18 | Gen Electric | Materiaal op basis van een van polymeriseerbare eindgroepen voorziene polyfenyleenether. |
| JPH0649788B2 (ja) * | 1990-01-23 | 1994-06-29 | 工業技術院長 | 熱可塑性樹脂成形体の表面活性化方法 |
| JPH0649789B2 (ja) * | 1990-01-23 | 1994-06-29 | 工業技術院長 | 熱可塑性樹脂成形体の表面活性化方法 |
| US5338796A (en) * | 1990-03-22 | 1994-08-16 | Montedipe S.R.L. | Thermoplastic composition based on polyphenylene ether and polyamide |
| US5024818A (en) * | 1990-10-09 | 1991-06-18 | General Motors Corporation | Apparatus for forming carbon fibers |
| DE4103140A1 (de) | 1991-02-02 | 1992-08-13 | Basf Ag | (omega)-(vinylbenzoyl)-poly-(2,6-dimethyl-1,4- phenylenether), verfahren zu ihrer herstellung und ihre verwendung zur herstellung von copolymeren |
| NL9100224A (nl) | 1991-02-08 | 1992-09-01 | Gen Electric | Werkwijze voor het bereiden van een mengsel van polyfenyleenether en polyvinylaromatische verbinding. |
| US5612425A (en) * | 1991-03-30 | 1997-03-18 | Basf Aktiengesellschaft | Molding compositions based on modified polyaryl ethers |
| US5591382A (en) * | 1993-03-31 | 1997-01-07 | Hyperion Catalysis International Inc. | High strength conductive polymers |
| US5407972A (en) * | 1993-08-02 | 1995-04-18 | Sunrez Corp. | Photocurable ethylenically unsaturated sulfide and polysulfide polymer compositions |
| US5965663A (en) * | 1995-06-06 | 1999-10-12 | Kabushiki Kaisha Toshiba | Resin composition and resin-molded type semiconductor device |
| EP0768334B1 (en) * | 1995-10-16 | 2004-02-18 | Sumitomo Chemical Company Limited | Prepreg, process for producing the same and printed circuit substrate using the same |
| EP0831119A2 (en) * | 1996-09-18 | 1998-03-25 | Daicel Chemical Industries, Ltd. | Corsslinkable polymer composition, molded article therefrom, process for the preparation thereof, crosslinked nonwoven cloth, and process for the preparation thereof |
| US5834565A (en) * | 1996-11-12 | 1998-11-10 | General Electric Company | Curable polyphenylene ether-thermosetting resin composition and process |
| US5922815A (en) * | 1997-12-15 | 1999-07-13 | General Electric Company | Process for producing blends of tackifying resins with low molecular weight polyphenylene ethers |
| US6365069B2 (en) * | 1999-03-19 | 2002-04-02 | Quantum Composites Inc. | Process of injection molding highly conductive molding compounds and an apparatus for this process |
| US6436315B2 (en) * | 1999-03-19 | 2002-08-20 | Quantum Composites Inc. | Highly conductive molding compounds for use as fuel cell plates and the resulting products |
| US6627704B2 (en) * | 1999-12-01 | 2003-09-30 | General Electric Company | Poly(arylene ether)-containing thermoset composition, method for the preparation thereof, and articles derived therefrom |
| US6352782B2 (en) * | 1999-12-01 | 2002-03-05 | General Electric Company | Poly(phenylene ether)-polyvinyl thermosetting resin |
| US6306963B1 (en) * | 2000-05-08 | 2001-10-23 | General Electric Co. | Thermosetting resins and laminates |
| US6384176B1 (en) * | 2000-07-10 | 2002-05-07 | General Electric Co. | Composition and process for the manufacture of functionalized polyphenylene ether resins |
| TWI254054B (en) * | 2000-12-19 | 2006-05-01 | Ind Tech Res Inst | Curable polyphenylene ether resin, composition made therefrom, and process for preparing the resin |
| US6593391B2 (en) * | 2001-03-27 | 2003-07-15 | General Electric Company | Abrasive-filled thermoset composition and its preparation, and abrasive-filled articles and their preparation |
| JP4007828B2 (ja) | 2002-03-08 | 2007-11-14 | 旭化成ケミカルズ株式会社 | 低分子量ポリフェニレンエーテルの製造方法 |
-
2001
- 2001-03-27 US US09/681,376 patent/US6878781B2/en not_active Expired - Lifetime
- 2001-11-14 EP EP01987045A patent/EP1373410B1/en not_active Expired - Lifetime
- 2001-11-14 WO PCT/US2001/043551 patent/WO2002077103A1/en active IP Right Grant
- 2001-11-14 DE DE60126345T patent/DE60126345T2/de not_active Expired - Lifetime
- 2001-11-14 JP JP2002576554A patent/JP4204325B2/ja not_active Expired - Fee Related
- 2001-11-14 CN CNB018231004A patent/CN100363425C/zh not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3597216A (en) * | 1969-09-24 | 1971-08-03 | Celanese Corp | High temperature photoresist of cross-linked poly(2,6-dimethyl-1,4-phenylene oxide) |
| CN1064088A (zh) * | 1991-01-11 | 1992-09-02 | 旭化成工业株式会社 | 可固化的聚苯氧树脂组合物及由此可获得的已固化树脂组合物 |
| JPH0812875A (ja) * | 1994-06-29 | 1996-01-16 | Matsushita Electric Works Ltd | ポリフェニレンオキサイド系成形材料の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1373410A1 (en) | 2004-01-02 |
| JP2004524412A (ja) | 2004-08-12 |
| WO2002077103A1 (en) | 2002-10-03 |
| DE60126345D1 (de) | 2007-03-15 |
| US20020173597A1 (en) | 2002-11-21 |
| JP4204325B2 (ja) | 2009-01-07 |
| US6878781B2 (en) | 2005-04-12 |
| EP1373410B1 (en) | 2007-01-24 |
| DE60126345T2 (de) | 2007-10-18 |
| CN1494574A (zh) | 2004-05-05 |
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