EP4352130A1 - Compositions contenant des polyorganosiloxanes ayant des groupes éther de polyphénylène - Google Patents
Compositions contenant des polyorganosiloxanes ayant des groupes éther de polyphénylèneInfo
- Publication number
- EP4352130A1 EP4352130A1 EP21732824.4A EP21732824A EP4352130A1 EP 4352130 A1 EP4352130 A1 EP 4352130A1 EP 21732824 A EP21732824 A EP 21732824A EP 4352130 A1 EP4352130 A1 EP 4352130A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- formula
- radical
- mol
- radicals
- compositions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 207
- 229920001955 polyphenylene ether Polymers 0.000 title claims abstract description 167
- 125000001033 ether group Chemical group 0.000 title description 7
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 claims abstract description 77
- 239000005046 Chlorosilane Substances 0.000 claims abstract description 75
- 238000000034 method Methods 0.000 claims abstract description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 40
- 238000004519 manufacturing process Methods 0.000 claims abstract description 35
- 150000002989 phenols Chemical class 0.000 claims abstract description 31
- 229920001577 copolymer Polymers 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 18
- 239000011230 binding agent Substances 0.000 claims abstract description 15
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 229920001519 homopolymer Polymers 0.000 claims abstract description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 36
- 230000008569 process Effects 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 22
- 125000000524 functional group Chemical group 0.000 claims description 15
- 229930195733 hydrocarbon Natural products 0.000 claims description 15
- 239000004215 Carbon black (E152) Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910010271 silicon carbide Inorganic materials 0.000 claims description 11
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910018540 Si C Inorganic materials 0.000 claims description 9
- 239000002131 composite material Substances 0.000 claims description 8
- 239000000835 fiber Substances 0.000 claims description 6
- 239000003365 glass fiber Substances 0.000 claims description 6
- 229910003849 O-Si Inorganic materials 0.000 claims description 4
- 229910003872 O—Si Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- OLRJXMHANKMLTD-UHFFFAOYSA-N silyl Chemical compound [SiH3] OLRJXMHANKMLTD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- -1 Polytetrafluoroethylene Polymers 0.000 description 115
- 150000003254 radicals Chemical class 0.000 description 87
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 84
- 238000002360 preparation method Methods 0.000 description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- 229910052710 silicon Inorganic materials 0.000 description 30
- 239000012071 phase Substances 0.000 description 29
- 238000005481 NMR spectroscopy Methods 0.000 description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 25
- 229920001296 polysiloxane Polymers 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000000523 sample Substances 0.000 description 20
- 238000001542 size-exclusion chromatography Methods 0.000 description 20
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 17
- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000007795 chemical reaction product Substances 0.000 description 15
- 230000009477 glass transition Effects 0.000 description 15
- 238000004627 transmission electron microscopy Methods 0.000 description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 14
- 238000005755 formation reaction Methods 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- 239000001257 hydrogen Substances 0.000 description 14
- 238000005259 measurement Methods 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 125000003545 alkoxy group Chemical group 0.000 description 13
- XSDCTSITJJJDPY-UHFFFAOYSA-N chloro-ethenyl-dimethylsilane Chemical compound C[Si](C)(Cl)C=C XSDCTSITJJJDPY-UHFFFAOYSA-N 0.000 description 13
- 239000005054 phenyltrichlorosilane Substances 0.000 description 13
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 13
- 239000010408 film Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 11
- 229920001400 block copolymer Polymers 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000000113 differential scanning calorimetry Methods 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
- 229920002223 polystyrene Polymers 0.000 description 11
- 239000010703 silicon Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229920002050 silicone resin Polymers 0.000 description 9
- 125000005842 heteroatom Chemical group 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229920013636 polyphenyl ether polymer Polymers 0.000 description 8
- 238000005160 1H NMR spectroscopy Methods 0.000 description 7
- QABCGOSYZHCPGN-UHFFFAOYSA-N chloro(dimethyl)silicon Chemical compound C[Si](C)Cl QABCGOSYZHCPGN-UHFFFAOYSA-N 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000006459 hydrosilylation reaction Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229920000620 organic polymer Polymers 0.000 description 7
- 125000004430 oxygen atom Chemical group O* 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- 125000006850 spacer group Chemical group 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 125000005372 silanol group Chemical group 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 238000005260 corrosion Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 229920000578 graft copolymer Polymers 0.000 description 5
- 229920005669 high impact polystyrene Polymers 0.000 description 5
- 239000004797 high-impact polystyrene Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 238000005691 oxidative coupling reaction Methods 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 4
- 239000003849 aromatic solvent Substances 0.000 description 4
- 238000000429 assembly Methods 0.000 description 4
- 230000000712 assembly Effects 0.000 description 4
- 230000007797 corrosion Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000005055 methyl trichlorosilane Substances 0.000 description 4
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000013557 residual solvent Substances 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 3
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 101150041968 CDC13 gene Proteins 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 229910002808 Si–O–Si Inorganic materials 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- IQYMRQZTDOLQHC-ZQTLJVIJSA-N [(1R,4S)-2-bicyclo[2.2.1]heptanyl] prop-2-enoate Chemical compound C1C[C@H]2C(OC(=O)C=C)C[C@@H]1C2 IQYMRQZTDOLQHC-ZQTLJVIJSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000004891 communication Methods 0.000 description 3
- 239000004567 concrete Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 229920003244 diene elastomer Polymers 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000000670 limiting effect Effects 0.000 description 3
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 3
- 238000000386 microscopy Methods 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000010453 quartz Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 3
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 3
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical class C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 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
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- ATGFTMUSEPZNJD-UHFFFAOYSA-N 2,6-diphenylphenol Chemical compound OC1=C(C=2C=CC=CC=2)C=CC=C1C1=CC=CC=C1 ATGFTMUSEPZNJD-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- CIRRFAQIWQFQSS-UHFFFAOYSA-N 6-ethyl-o-cresol Chemical compound CCC1=CC=CC(C)=C1O CIRRFAQIWQFQSS-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 238000010504 bond cleavage reaction Methods 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
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001733 carboxylic acid esters Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000010382 chemical cross-linking Methods 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
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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 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
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- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl 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])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002086 nanomaterial Substances 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
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229920003986 novolac 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
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
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- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 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
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- ZDHXKXAHOVTTAH-UHFFFAOYSA-N trichlorosilane Chemical compound Cl[SiH](Cl)Cl ZDHXKXAHOVTTAH-UHFFFAOYSA-N 0.000 description 1
- 239000005052 trichlorosilane Substances 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- CEAWWDXUKYZTJL-UHFFFAOYSA-N triethyl(phenyl)silane Chemical compound CC[Si](CC)(CC)C1=CC=CC=C1 CEAWWDXUKYZTJL-UHFFFAOYSA-N 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/48—Polymers modified by chemical after-treatment
- C08G65/485—Polyphenylene oxides
Definitions
- the invention relates to a process for the production of compositions in which polyphenylene ethers or phenols are reacted with chlorosilane alone or in a mixture with disiloxane, the compositions obtainable by the process and their use.
- Polyorgansiloxanes have excellent heat resistance, weathering stability and hydrophobic properties, are flame-resistant and have low dielectric loss factors.
- US Pat. No. 6,258,881 describes polyphenylene ether compositions which are rendered flame-resistant by the addition of silicones, it being possible to dispense with the addition of flame-retardants.
- the compositions are physical mixtures of polyphenylene ethers and optionally other organic polymer components and the silicone building blocks. Good compatibility of the two preparation components is therefore essential in order to achieve the desired flame resistance effect. This is only achieved with a certain ratio of Si-C-bonded methyl groups and phenyl groups on the silicone building block. Pure methyl resins cannot be used here, nor can pure phenyl resins.
- other properties of the preparation are also determined by the ratio of silicon-bonded methyl and phenyl groups, such as mechanical properties expressed as impact strength.
- the silicone component forms the dispersed phase in the continuous phase of the polyphenylene ether in the compositions.
- US Pat. No. 6,258,881 teaches that only certain particle sizes of the dispersed silicone particles in the polyphenylene ether phase permit adequate flame resistance. If the particle size is too large, further negative side effects such as delamination effects can occur.
- the silicone components which achieve the effect according to the invention according to US Pat. No. 6,258,881 are preferably solids, since liquid silicone components may not disperse sufficiently well in the polyphenylene ethers. Further examples of the use of compositions of physical blends of polyphenylene ethers with polyorganosiloxanes to improve specific properties can be found in US 3737479 (improving impact strength),
- US 5357022 teaches flame retardant silicone - polyphenylene ether block copolymers obtained by the oxidative coupling of phenol terminated polydiorganosiloxane macromers and alkyl or aryl substituted phenols. The method is limited to maximally doubly functionalized polydiorganosiloxane macromers with a terminal arrangement of the phenolic functions. Unreactive thermoplastic block copolymers are obtained which no longer have any functional groups for further chemical crosslinking.
- Polyphenylene ether block copolymers by reacting alpha-omega amine-terminated polydiorganosiloxanes with anhydride-functional polyarylene ethers. In this case, too, the reaction is limited to difunctional siloxane species, and the functional groups present are consumed in the formation reaction of the block copolymer, so that no further functional groups are present for chemical crosslinking.
- US 2016/0244610 describes compositions from mixtures of olefinically unsaturated MQ resins with unsaturated modified polyphenylene ethers, the dielectric and thermal properties of the polyphenylene ethers being said to be improved through the use of the MQ resin.
- the examples in US 2016/0244610 show very high dielectric loss factors of the compositions according to the invention.
- US 2018/0220530 also describes compositions made from mixtures of silicone resins, in this case of the MT, MDT, MDQ and MTQ type, which are claimed as a lump sum and as classes without further restrictions.
- compositions according to US 2018/0215971 and US 2018/0220530 show according to the embodiments of the two inventions particularly good suitability for the production of high-frequency printed circuit boards. It is noticeable that this prior art makes no reference whatsoever to the compatibility of the silicone resins and polyphenylene ethers resulting from the composition according to the invention with one another. Since the silicone resins are claimed as entire classes, part of the teaching of this prior art consists in the fact that both compositions made from compatible and from incompatible mixtures of silicone resins with polyphenylene ethers achieve the stated object equivalently. As already explained above, this is not plausible for a person skilled in the art.
- Polydiorganosiloxanes are less suitable for use than the MT, MDT, MDQ, MTQ, TT and TQ resins of the invention because the vinyl-functional polydiorganosiloxanes used either lead to a reduction in flexural strength or are volatile under the curing conditions used.
- a comparatively used DT resin in the examples which, in contrast to the TT and TQ resins according to the invention, does not contain any olefinically unsaturated groups, is also not inventive and therefore excluded from the scope of the claim, because the mechanical and thermal performance of this resin for the target application as are insufficiently described. This apparently prompts the inventor to the conclusion that vinyl-functional DT resins cannot be according to the invention either if they are completely excluded from the scope of the claim.
- US 2018/0215971 and US 2018/0220530 aim for a dielectric loss factor of ⁇ 0.007. This requirement is met with freshly produced test specimens from the materials according to the invention, although not significantly below it.
- What US 2018/0215971 and US 2018/0220530 do not show is how long-term reliability of the specimen according to the invention is ordered, ie the constancy of the dielectric properties under load conditions. This would be particularly relevant with regard to the compatibility or incompatibility between the components that make up the binder, which is not considered in US 2018/0215971 and US 2018/0220530. As could be shown here, this reliability under load conditions does not actually exist, so that the prior art according to US 2018/0215971 and US 2018/0220530 leaves room for improvement.
- compositions of silane-terminated, olefinically unsaturated polyphenylene ethers obtained from the reaction of chlorine-functional silanes and hydroxy-terminated polyphenylene ethers in an anhydrous environment, with unbranched, linear or cyclic, olefinically unsaturated or Si—H-functional polydiorganylsiloxanes.
- the compositions are cured free-radically or by hydrosilylation.
- the silane units are bonded to the polyphenylene ether units exclusively through Si-OC bonds. It is known that these bonds are sensitive to hydrolysis. With access of water and optionally temperature and optionally catalytically active traces of acid, an Si-OC bond is reformed with reformation of the OH-terminated polyphenylene ether and a Si-O-Si coupling, intermediately if necessary with the formation of silanol species.
- the polyphenylene ethers are connected to the olefinically unsaturated or Si-H-functional polydiorganosiloxanes only via the olefinically unsaturated silane units, the physically mixed components of the crosslinked polydiorganosiloxane and the original polyphenylene ether are present after hydrolysis of the Si-OC bonds of the silane termination.
- the result essentially corresponds to what one would expect if the polyphenyl ethers were mixed with the olefinically unsaturated polydiorganosiloxanes without prior silane termination and the siloxane units were then cured by free radicals.
- the object of the invention is to provide compatible compositions of polyorganosiloxanes with polyphenylene ethers that are suitable for use in high-frequency applications and overcome the disadvantages of the prior art.
- compositions in which a) compounds selected from hydroxy-terminated homopolymers or copolymers of polyphenylene ethers and phenols with b) chlorosilane of the formula (I) alone or in admixture with disiloxane of the formula (IV)
- compositions which can be prepared from a) compounds which are selected from hydroxy-terminated homopolymers or copolymers of polyphenylene ethers and phenols with b) chlorosilane of the formula (I) alone or in a mixture with disiloxane of the formula (IV)
- R 1 is identical or different, optionally substituted with heteroatoms, aliphatic, cycloaliphatic or aromatic CI - C12 radicals, the proportion of those Chlorosilanes of the formula (I) which have an aromatic radical is to be chosen such that in the chlorosilane of the formula (I) the proportion of aromatic substituents is based on 100 mol% of all silicon-bonded radicals through a Si—C bond is at least 10 mol%,
- compositions solve the problem.
- the compositions are homogeneous and stable as the hydrolysis becomes steady state under controlled conditions resulting in a physical mixture from the start and in this way the performance stabilized product mixture is used as a binder.
- the performance requirements for use in high-frequency applications are met.
- the compositions according to US 2020/0283575 cannot do that.
- compositions contain polyphenylene ethers, polyorganosiloxanes containing polyphenylene ether radicals and optionally polyorganosiloxanes which have no polyphenylene ether radicals.
- polyorganosiloxanes which can be prepared by the process and which have polyphenylene ether radicals are also a subject of the invention.
- Subsequent work-up in the process is preferably carried out by methods according to the prior art, comprising the steps of phase separation, neutral washing, if appropriate mixing with further polyphenylene ethers and devolatilization, it being possible for the order of the steps to be adapted as required.
- the proportion of those chlorosilanes of the formula (I) which have an aromatic radical should preferably be chosen such that the proportion of aromatic substituents in the polyorganosiloxane formed from the chlorosilane of the formula (I) or a mixture of different chlorosilanes of the formula (I) based on 100 mol% of all silicon-bonded radicals introduced by the chlorosilane(s) of the formula (I) through a Si-C bond, is at least 15 mol%, in particular at least 20 mol%.
- Polyorganosilane lead to so-called M-units, which in the present case according to the invention have the formulas (R 1 2R 2 SiOi / 2), (R 1 R 2 SiOi / 2), (R 1 3 SiOi / 2) or (R 2 3 SiOi / 2) obey, where R 1 and
- R 2 have the meanings given above.
- the polyorganosiloxanes of the invention can also contain components of the formulas (R 1 Si0 2/2) , (R 3 2SiC> 2 / 2) or (R 1 R 3 Si0 2/2) and (S1O4 / 2) from the corresponding Chlorosilanes of the formula (I) are accessible, where R 1 and R 3 have the meaning given above.
- polyorganosiloxanes according to the invention containing phenyl groups and having polyphenylene ether radicals are isolated, which are obtained in the present invention in the form of the partially hydrolyzed copolymers of polyorganosiloxanes containing phenyl groups with polyphenylene ethers or unsubstituted phenol or substituted phenols, they preferably have average molecular weights Mw in the range from 500 to 300,000 g/mol, preferably from 600 to 100000 g/mol, particularly preferably from 600 to 60000 g/mol, in particular from 600 to 40000 g/mol, the polydispersity being at most 20, preferably at most 18, particularly preferably at most 16, in particular at most 15 is.
- the phenyl-containing polyorganosiloxanes are solid at 25° C., with the solid phenyl-containing polyorganosiloxanes
- Glass transition temperatures in the uncrosslinked state in the range from 25° C. to 250° C., preferably from 30° C. to 230° C., in particular from 30° C. to 200° C., or they are liquid with viscosities at 25° C. from 20 to 8000 000 mPas, preferably from 20 to 5,000,000 mPas, in particular from 20 to 3,000,000 mPas.
- Those polyorganosiloxanes containing phenyl groups which are solid at 25° C. and have a glass transition temperature of 45-200° C. have proven to be particularly suitable which are liquid with a viscosity between 300 and 1000 000 mPas.
- R 1 are alkyl radicals, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, iso -Pentyl, neo-pentyl, tert-pentyl, hexyl, such as n-hexyl, heptyl, such as n-heptyl, octyl, such as n-octyl, and iso-octyl, such as 2,2,4- Trimethylpentyl radical, nonyl radicals such as the n-nonyl radical, decyl radicals such as the n-decyl radical, dodecyl radicals such as the n-dodecyl radical and octadecyl radicals such as the n-octadecyl radical,
- the radical R 1 is preferably an unsubstituted hydrocarbon radical having 1 to 12 carbon atoms, particularly preferably the methyl, ethyl and n-propyl radical and phenyl radical, in particular the methyl, n-propyl and phenyl radical.
- the methyl radical and the phenyl radical are particularly preferred.
- Polyorganosiloxanes with polyphenylene ethers form phase boundaries between the silicone domains and the surrounding organic polymer due to the incompatibility. At such phase boundaries, air inclusions and, as a result, the incorporation of moisture cannot be ruled out.
- radicals R 2 are acrylate and methacrylate radicals, such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate,
- radicals R 2 are olefinically or acetylenically unsaturated hydrocarbon radicals of the formulas (II) and (III)
- YC ⁇ CR 7 (III), where Y is a chemical bond or a divalent linear or branched hydrocarbon radical having up to 30 carbon atoms, where Y can also contain olefinically unsaturated groups or heteroatoms and the atom directly bonded to the silicon by the radical Y is a carbon is.
- radicals (II) are the vinyl radical, the propenyl radical and the butenyl radical, in particular the vinyl radical.
- the radical (II) can also mean a dienyl radical bonded via a spacer, such as the 1,3-butadienyl radical bonded via a spacer or the isoprenyl radical.
- radicals R 2 are hydridic silicon-bonded hydrogen.
- the radicals R 2 are generally not bonded directly to the silicon atom.
- An exception to this are the olefinic or acetylenic groups, which can also be directly silicon-bonded, especially the vinyl group.
- the other functional groups R 2 are bonded to the silicon atom via spacer groups, the spacer always being Si—C bonded.
- the spacer is a divalent hydrocarbon radical which comprises 1 to 30 carbon atoms and in which non-adjacent carbon atoms can be replaced by oxygen atoms and which can also contain other heteroatoms or heteroatom groups, although this is not preferred.
- the methacrylate group and the acrylate group are preferably bonded via a spacer, the spacer having 3 to 15 carbon atoms, preferably in particular 3 to 8 carbon atoms, in particular 3 carbon atoms and optionally also at most one to 3 oxygen atoms, preferably at most one oxygen atom comprehensive divalent hydrocarbon radical bonded to the silicon atom.
- suitable solvents are aromatic solvents such as toluene, xylene, ethylbenzene or mixtures thereof and hydrocarbons or mixtures thereof such as commercially available isoparaffin mixtures.
- Alcohols as well as liquid polyols and organic carboxylic acid esters such as those of acetic acid, such as ethyl acetate, butyl acetate, methoxypropyl acetate, are not suitable because they lead to the introduction of additional alkoxy groups into the polyorganosiloxane structure, which should be avoided since these can be damaged under the influence of temperature Condensation with elimination of volatile alcohols in the hardened binder matrix could lead to blisters. The content of condensable groups should therefore be kept to a minimum. The process described in detail further below therefore takes this claim of alkoxy-freedom into account in a special way. Consequently, alkoxy-free products are obtained.
- the chlorosilanes of the formula (I) are used in a mixture with one or more disiloxanes of the formula (IV), then, based on the amount used, the chlorosilanes are 100 mol %, preferably at most 50 mol %, particularly preferably at most 40 mol -%, in particular at most 30 mol% used.
- polyphenylene ethers used according to the invention which are reacted according to the process as described in detail below, are hydroxy-terminated functional homopolymers or copolymers, which can preferably be prepared by repeated oxidative coupling of at least one type of phenol component of the formula (V), in Presence of oxygen or an oxygen-containing gas and an oxidative coupling catalyst.
- R 8 , R 9 , R 10 , R 11 and R 12 independently represent a hydrogen radical, a
- Hydrogen radical where preferably the radical R 10 is a hydrogen radical.
- radicals R 8 , R 9 , R 10 , R 11 and R 12 in formula (V) are the hydrogen radical, saturated hydrocarbon radicals such as methyl, ethyl, n-propyl, isopropyl, the primary, secondary and tertiary butyl radical, the hydroxyethyl radical, aromatic radicals such as the phenylethyl radical, the phenyl radical, the benzyl radical, the methylphenyl radical, the dimethylphenyl radical, the ethylphenyl radical, heteroatom-containing radicals such as the hydroxymethyl radical, the carboxyethyl radical, the methoxycarbonylethyl radical and the cyanoethyl radical and acrylate and methacrylate radicals such as methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, propyl acrylate, propyl methacrylate, n-butyl acrylate,
- adjacent radicals R 8 and R 9 and the adjacent radicals R 11 and R 12 can also be connected to one another to form the same cyclic saturated or unsaturated radical, so that fused polycyclic structures are formed.
- phenolic compounds of formula (V) are phenol, ortho-, meta- or para-cresol, 2,6-, 2,5-, 2,4- or 3,5-dimethylphenol, 2-methyl-6-phenylphenol, 2,6-diphenylphenol,
- Preferred phenolic compounds of formula (V) are 2,6-dimethylphenol, 2,6-diphenylphenol, 3-methyl-6-tert-butylphenol and 2,3,6-trimethylphenol.
- the phenolic compounds according to formula (V) can be copolymerized with polyhydric aromatic compounds such as bisphenol A, resorcinol, hydroquinone and novolak resins.
- these copolymers are also included under the term polyphenylene ether.
- the oxidative coupling catalyst used for the oxidative copolymerization of said phenyl compounds is not particularly limited. In principle, any catalyst that has the ability to catalyze oxidative coupling can be used.
- polyphenylene ethers of the present invention are poly(2,6-dimethyl-1,4-phenylene ether),
- polyphenylene ether examples include those from higher substituted phenols, such as 2,3,6-trimethylphenol and 2,3,5,6-tetramethylphenol with a substituted in the 2-position phenol such as 2,6-dimethylphenol.
- Preferred polyphenylene ethers from the list above are poly(2,6-dimethyl-1,4-phenylene ether) and copolymers of 2,6-dimethylphenol with 2,3,6-trimethylphenol and of 2,6-dimethylphenol with bisphenol A.
- the polyphenylene ethers used according to the invention can be graft copolymers obtained by grafting with the abovementioned polymers and copolymers Styrene components such as styrene, alpha-methyl styrene, para-methyl styrene and vinyl styrene. Such graft copolymers are also included within the scope of this invention.
- the polyphenylene ethers can be used in combination with other components, such as thermoplastic polymers such as polystyrene, styrene-based elastomers and polyolefins, which are optionally used to specifically improve individual properties, such as processability and impact strength and optionally other properties. These components are referred to herein as component (C).
- Polystyrene means that at least 25% by weight of the repeating units are of vinyl aromatic origin and are represented by the following formula (VI).
- R 13 represents a hydrogen radical or a hydrocarbon group having 1 - 4 carbon atoms such as a methyl group, an ethyl group, a propyl group or a butyl group.
- Z is an alkyl group having 1-4 carbon atoms such as a methyl group, an ethyl group, an
- HIPS forming diene rubber examples include homopolymers and copolymers of conjugated dienes such as butadiene, isoprene and chloroprene, copolymers of said conjugated dienes with unsaturated nitrile components such as acrylonitrile and methacrylonitrile and/or aromatic vinyl compounds such as styrene, alpha- and para-methylstyrene, chlorostyrene and bromostyrene, natural rubbers and their mixtures.
- conjugated dienes such as butadiene, isoprene and chloroprene
- unsaturated nitrile components such as acrylonitrile and methacrylonitrile and/or aromatic vinyl compounds
- styrene, alpha- and para-methylstyrene, chlorostyrene and bromostyrene natural rubbers and their mixtures.
- Preferred diene rubbers are polybutadienes and butadiene-styrene copolymers.
- the manufacturing processes for the HIPS are known from the prior art and include the processes of emulsion polymerization, suspension polymerization, bulk polymerization, solution polymerization and combinations thereof.
- the polystyrene content, if present in the polyphenylene ether, is preferably between 1 and 1000 parts by mass, particularly preferably between 10 and 500 parts by mass, based on 100 parts by mass of polyphenylene ether.
- Styrene-based elastomers are well known in the art. Your choices are in no way particularly limited.
- Examples are styrene-butadiene block copolymers with at least one polystyrene block and at least one polybutadiene block, styrene-isoprene copolymers with at least one polystyrene block and at least one polyisoprene block, block copolymers with at least one polystyrene block and at least one isoprene-butadiene copolymer block, block copolymers in which unsaturated bond portions of the polyisoprene block, des polybutadiene blocks and the isoprene-butadiene copolymer block in the above block copolymers are selectively hydrogenated and further referred to as hydrogenated block copolymers, and graft copolymers obtained by graft polymerization of a polyolefin elastomer with styrene, wherein the polyolefin
- Elastomer is made by the copolymerization of two or more monomers selected from the group of ethylene, propylene, butenes and the conjugated dienes mentioned above, the graft copolymer being further referred to herein as a styrene-grafted polyolefin.
- the hydrogenated block copolymers and the styrene-grafted polyolefins are preferred.
- the polyolefins are in no way particularly limited and include those known in the art.
- polyolefins examples include polyethylene, polypropylene, polybutene, polypentene, ethylene-vinyl acetate copolymers, ethylene-vinyl alcohol copolymers, ethylene-propylene rubbers and ethylene-propylene-diene rubbers.
- the polyphenylene ethers used according to the invention are preferably not graft copolymers.
- Preferred polyphenylene ethers used according to the invention which are reacted with chlorosilanes of the formula (I) and optionally disiloxanes of the formula (IV) in the process according to the invention, have the formula (VII), as described, these can be grafted with polystyrene copolymers, but are preferably not.
- R 8 , R 9 , R 11 and R 12 independently have the meanings given above.
- the radical R 14 is a chemical bond or a divalent, optionally substituted arylene radical of the form (-C6R 15 4-), where R 15 independently of this can have the same meaning as the radicals R 8 , R 9 , R 11 or R 12 or an alkylene radical of the form -CR 16 2-, where R 16 independently of R 15 can have the same meanings as R 15 , a divalent glycol radical of the form -[(OCH 2 )2O] f - or -[(OCH 2 CH ( CH 3 ) 2 )0] g -, where f and g can each independently be integers from 1 to 50 inclusive, a divalent silyloxy radical of the form -Si(R 17 )2O2 / 2 / a divalent siloxane radical of the form -[(CH2) 3 S1-[O-Si(R 18 )2]hO-Si(012)3-, a divalent silyl radical of the form -Si(R
- Preferred radicals R 14 are the chemical bond, the -CH2- radical, the C(CH 3 )- radical, the -0(0 6 H 5 )- radical and the -[(CH 2 ) 3 S1-[0- Si (R 18 ) 2 ]O-Si(CH 2 ) 3 radical, c, d and e are integers, where c is an integer having a value from 2 to 50 inclusive, d is an integer having a value of each 1 to 10 inclusive and e is an integer having a value of 2 to 50 inclusive.
- polyphenylene ether radicals in particular partially hydrolyzed polyorganosiloxane-polyphenylene ether copolymers or partially hydrolyzed polyorganosiloxane-phenol copolymers, which are obtained by reacting the chlorosilanes of the formula (I) and, if appropriate, the disiloxanes of the formula (IV) with polyphenylene ethers of the formula (VII) or phenols of formula (V), have the formula (VIII),
- R 1 and R 3 have the meanings given above, i can be an integer with the values 0, 1, 2 or 3, but preferably has the values 0 or 1, in particular the value
- 1, k can be an integer with a value of 0, 1 or 2, preferably the values 0 or 1, in particular the value 0, j, 1, m, n and o are integers, where j has the values 0 to 50 may have,
- 1 can assume the values 0 to 1900, m can assume the values 0 to 2500, n can assume the values 0 to 2000, where m+n > 2 o can assume the values 0 to 75, where the value m+n is am Total value j + l + m + n + o is at least 20%, preferably at least 30%, in particular at least 40%, the value of 1 has a share of at most 50%, in particular at most 30%, the value of j has a share of at most 80 % of the total, the value of j preferably accounting for 10 to 50% of the total and the value of o accounting for at most 50%, in particular has at most 30% of the sum, where the sum is j+l+m+n+o > 6.
- assemblies (R 1 -k R 3 k Si0 2/2 )i, (R 1 Si0 3/2 ) m/ (R 3 Si0 3/2 ) n and (S1O4/2) 0 units themselves alternate statistically in the molecular structure, or there are blocks of several repeating units of the same form, i.e.
- a sufficient amount of Si—C-bonded aromatic radicals R 1 must always be present in the polyorganosiloxanes of the formula (VIII). It is irrelevant here whether the radicals R 1 are bonded to an M, D or T unit.
- An M unit is a siloxane unit that has three Si-C-bonded radicals and is bonded through an oxygen atom to an adjacent silicon atom and so on in the others
- a D unit is a siloxane unit that has two Si-C-bonded radicals and is bonded to adjacent silicon atoms through two oxygen atoms and is thus incorporated into the remainder of the polyorganosiloxane structure.
- a T unit is a siloxane unit that has a Si-C bonded radical and is bonded to adjacent silicon atoms through three oxygen atoms and is thus incorporated into the remainder of the polyorganosiloxane structure.
- aromatic Si—C bonded radicals R 1 based on all Si—C bonded aromatic and aliphatic radicals calculated as 100 mol %, particularly preferably at least 20 mol %, in particular at least 25 mol %.
- the preferred aromatic radical R 1 is the phenyl radical.
- the polyorganosiloxanes of the formula (VIII) according to the invention also have at least 0.3 mol % Si-OC-bonded, optionally substituted phenol radicals, such as are obtained from formula (V) by abstraction of the phenolic hydrogen atom and addition of the resulting phenol radical to a silicon-bonded oxygen or polyphenylene ether radicals such as are obtained from formula (VII) by abstraction of at least one terminal phenolic hydrogen atom and addition of the resulting polyphenylene ether radical to a silicon-bonded oxygen as radicals R 3 .
- At least 0.4 mol %, in particular at least 0.5 mol %, of such radicals R 3 are preferably present.
- the method according to the invention is particularly efficient when the molar ratio of all Si—C-bonded aromatic and aliphatic radicals R 1 is expressed as the fraction
- the values of the mole fraction given above are preferably between 0.1 and 0.95, particularly preferably between 0.2 and 0.95, in particular between 0.4 and 0.8.
- the most preferred aliphatic radical R 1 is the methyl radical.
- the most preferred combination of aromatic and aliphatic radicals is the combination of phenyl radicals with methyl radicals.
- polyphenylene ethers used according to the invention can be added to the reaction products obtained, which differ from those for reaction with the chlorosilanes of the formula (I) and the disiloxanes of the formula (IV) can, but do not have to, differ from the polyphenylene ethers used.
- these additionally admixed polyphenylene ethers can contain further radicals on the phenolic oxygen atom, as have been described for the radicals R 8 , R 9 , R 10 , R 11 and R 12 , ie other than the hydrogen atom.
- polyphenylene ethers substituted on the phenolic oxygen in the reaction with chlorosilanes of the formula (I) and the disiloxanes of the formula (IV), but this is not preferred in order to rule out any disruptive side reactions of the functional groups bonded to the phenolic oxygen . It is preferred to use only the polyphenylene ethers which are reactive toward the chlorosilanes and have an unsubstituted phenolic OH group. In any case, it is necessary to use at least one species of polyphenyl ethers or phenols in the process of the invention is reactive towards chlorosilanes via an unsubstituted phenolic OH group.
- Fillers may be incorporated into the compositions of the present invention without any particular restriction on their selection.
- reinforcing fibers are glass fibers, carbon fibers or aramid fibers, glass fibers being preferred.
- Inorganic fillers are silica, alumina, calcium carbonate, talc, mica, clay, kaolin, magnesium sulfate, carbon black, titanium dioxide, zinc oxide, antimony trioxide, and boron nitride.
- Further examples of other components are antioxidants, stabilizers against weather degradation, lubricants, flame retardants, plasticizers, coloring agents, antistatic agents and mold release agents.
- compositions according to the invention are chemically curable, ie they can be cured by a chemical reaction to form a crosslinked, insoluble network. Curing takes place via the organofunctional groups R 2 , which are described above. Typically, either a free-radical polymerization reaction is used for curing or, if silicon-bonded hydrogen is also present as a radical in addition to the olefinically or acetylenically unsaturated functional groups R 2 , hydrosilylation curing is used.
- compositions are to be cured, a sufficient amount of functional groups is preferably present. At least an average of 1.2 functional groups must be present per molecule of the polyorganosiloxanes containing polyphenylene ether radicals in order to achieve adequate curing; an average of at least 1.5, in particular an average of at least 1.8, functional groups per molecule of the polyorganosiloxanes containing polyphenylene ether radicals is preferred have, present.
- suitable initiators for starting the free-radical polymerization are, in particular, examples from the field of organic peroxides, such as di-tert-butyl peroxide, dilauryl peroxide, dibenzoyl peroxide,
- dicetyl peroxydicarbonate dicetyl peroxydicarbonate, acetylacetone peroxide,
- compositions which, in addition to olefinically and acetylenically unsaturated groups, also contain silicon-bonded hydrogen there is the possibility of curing by a hydrosilylation reaction.
- Suitable catalysts for promoting the hydrosilylation reaction are those known in the art. Examples of such catalysts are compounds or complexes from the group of noble metals containing platinum,
- Ruthenium, iridium, rhodium and palladium preferably metal catalysts from the group of platinum metals or compounds and complexes from the group of platinum metals.
- metal catalysts are metallic and finely divided platinum, which can be on supports such as silicon dioxide, aluminum oxide or activated carbon, compounds or complexes of platinum such as platinum halides, e.g.
- ammonium platinum complexes In a further embodiment of the process according to the invention, complexes of iridium with cyclooctadienes, such as, for example, m-dichlorobis(cyclooctadiene)diiridium (I), are used.
- hydrosilylation catalysts is a dynamic field of research that constantly produces new active species that can of course also be used here. It is preferably the
- Hydrosilylation catalyst is platinum compounds or complexes, preferably platinum chlorides and platinum complexes, in particular platinum-olefin complexes and particularly preferably platinum-divinyltetramethyldisiloxane complexes.
- the hydrosilylation catalyst is used in amounts of 2 to 250 ppm by weight, based on the total compositions, preferably in amounts of 3 to 150 ppm, in particular in amounts of 3 to 50 ppm.
- polyphenylene ethers used for the reaction with the chlorosilanes of the formula (I) can be admixed to the resulting compositions according to the invention in order to set a higher proportion of organic components in the mixture, if necessary.
- Suitable for this purpose are both the polyphenylene ethers used for the reaction with the chlorosilanes of the formula (I) and polyphenylene ethers which differ therefrom.
- Polyphenylene ethers substituted on the phenolic oxygen which can be used as a further blending component are, for example, those of the formula (IX) where the radicals R 8 , R 9 , R 11 , R 12 and R 14 have the meanings given above and
- R 15 is a mono- or polyunsaturated aliphatic, cycloaliphatic C2 - C18 hydrocarbon radical which can contain additional heteroatoms and other functional groups and which can be replaced by other aromatic Hydrocarbon groups may be substituted, where R 15 may also be present with one other than one carbon atom bonded to the phenolic oxygen.
- the radical R 15 can also contain silyl groups in which the silicon atom is bonded directly to the phenolic oxygen and the unsaturated hydrocarbon radical is bonded to the silicon atom.
- polyphenylene ethers substituted with silyl groups reference is made to the polyphenylene ethers of the formula (I) in US 2020/0283575. Otherwise are examples of unsaturated
- Hydrocarbon radicals R 15 are the same as have already been indicated above for R 2 .
- compositions according to the invention are produced in a process which preferably comprises the following process steps:
- step 5 purification of the resulting mixture of polyphenylene ether, polyorganosiloxanes containing polyphenylene ether residues and, if appropriate, polyorganosiloxanes containing no polyphenylene ether residues, by phase separation and neutral washing, 6) followed, if appropriate, by mixing the product from step 5 with further polyphenylene ether, preferably according to formula (IX) and subsequent devolatilization, in particular when polyorganosiloxane copolymers were prepared with phenols and no polyphenylene ethers were present by the end of step 5.
- polyphenylene ether preferably according to formula (IX) and subsequent devolatilization, in particular when polyorganosiloxane copolymers were prepared with phenols and no polyphenylene ethers were present by the end of step 5.
- devolatilization takes place immediately after step 5.
- the product mixture can also be isolated after step 5 and then mixed in a separate step with further polyphenylene ether, optionally in the melt or with the aid of a suitable solvent, for example as part of the production process of a binder bath solution for the production of fiberglass composites for copper-clad laminates.
- organic polymers other than polyphenylene ethers can also be added here, such as polystyrene, polyolefins, bismaleimides,
- Bismalimide triazines Bismalimide triazines, polybenzoxazines, cyanate ester resins or epoxy resins.
- the starting material according to step 1) can be prepared by simply combining the chlorosilanes of the formula (I), optionally the disiloxanes of the formula (IV) and the polyphenylene ethers of the formula (VII) and/or the phenols of the formula (V) by successive dissolution or mixing of the individual components, it being preferred to first dissolve the polyphenylene ether or the phenols and then to add the chlorosilane(s) of formula (I) and optionally the disiloxane(s) of formula (IV).
- the order of addition of the chlorosilane or chlorosilanes according to formula (I) and optionally the disiloxane or disiloxanes according to formula (IV) is arbitrary.
- Preferred aromatic solvents are toluene, xylene as pure isomers or as a mixture of isomers, or ethylbenzene, which can be used alone or as a mixture.
- a special feature of the process is that no alcohols are used to stabilize the polyorganosiloxanes being formed against unwanted gelling. There is also no use of carboxylic acid esters, which also counteract unwanted gelling of the polyorganosiloxane by accelerating the rapid transfer of the initially hydrophilic and water-soluble polyorganosiloxane partial hydrolyzate that forms from the water phase into the organic phase. Any other phase mediator is also dispensed with in the synthesis.
- the polyorganosiloxane has only OH groups as silanol groups, these being present in small amounts, usually less than 1 percent by weight.
- Hydrochloric acid is formed from the chloride residues of the chlorosilanes of the formula (I) during the reaction with water.
- the water phase in step 2) can be chosen in such a way that it cannot completely absorb the hydrochloric acid formed, so that hydrochloric acid is consumed as a gas and can optionally be collected for recycling.
- the water phase can also be selected in such a way that the hydrochloric acid that forms is completely dissolved in it and no hydrochloric acid gas is consumed.
- the design of the water phase is essentially determined by the apparatus used and the technical variant. If the formation of a fuming hydrochloric acid cannot be tolerated in terms of apparatus technology, it is preferable to choose the water phase in such a way that a 5-30%, particularly preferably a 10-30%, particularly preferably a 20-30% aqueous hydrochloric acid solution is formed.
- the chlorosilanes of the formula (I) When the chlorosilanes of the formula (I) are mixed with phenol, substituted phenols or polyphenylene ethers, the corresponding condensation products of the respective chlorosilanes with phenol, the substituted phenols or the polyphenylene ethers are initially formed in an anhydrous environment. These are Si-O-C bonded condensation products.
- the chlorosilanes of the formula (I) react faster the more chlorine atoms they contain.
- a trichlorosilane reacts more rapidly with an Si-Cl bond than a dichlorosilane, which in turn reacts more rapidly than a monochlorosilane.
- the condensation products between phenol or the substituted phenols or the polyphenylene ethers with the most chloro-substituted chlorosilane of the formula (I) are preferably found in the mixture of different silanes.
- the starting material thus comprises a mixture of unmodified chlorosilanes of the formula (I), chlorosilanes of the formula (I) condensed with the phenols of the formula (V) or the polyphenylene ethers of the formula (VII), phenols of the formula (V), polyphenylene ethers of the formula ( VII) and optionally disiloxanes of the formula (IV) and an aromatic solvent, depending on the selected relative ratio of these components in different relative proportions.
- This mixture is understood by the term reactant template.
- step 2) It is preferred to use a pH-neutral water seal in step 2), so that no acid is present in the water phase is before step 3) occurs.
- the reaction proceeds autocatalytically due to the hydrochloric acid that forms.
- Several reactions take place.
- the chlorine atoms of the chlorosilanes of the formula (I) split off HCl as a result of the reaction with water and at the same time add OH groups to form silanoics which are unstable under the conditions of acidic hydrolysis and are formed by condensation with elimination of water and formation of Si-O- Si bridges form polyorganosiloxanes.
- Si-OC bonds of the condensation products of the chlorosilanes of the formula (I) with phenols of the formula (V) and the polyphenylene ethers of the formula (VII) are cleaved under the hydrolytic conditions, with a stable equilibrium between Si-OC bond cleavage and Condensation sets, which is on the side of the Si-OC bond cleavage under the chosen conditions, so that only a stable proportion of intact Si-OC bonds remains.
- Stable Si-O-Si bonds are formed from the cleaved Si-OC bonds on the one hand, and the OH-functional polyphenylene ethers on the other. This happens uniformly in the mixed reaction reactor, so that a homogeneous product mixture is obtained.
- the silicone phase forms a water-immiscible phase.
- a two-phase reaction mixture is obtained, which is then purified in step 5).
- These process steps for work-up 5) can be carried out in any convenient order, where the expediency can be determined by the properties of the silicone phase that occur in the meantime, such as the viscosity, the phase arrangement, etc.
- the work-up 5) is carried out, for example, by separating the aqueous phase from the silicone phase, then washing the silicone phase until neutral with neutral or basic water and then distilling the silicone phase. This purification, including devolatilization, concludes the process according to the invention.
- the washing water can be made alkaline, for example, by adding sodium bicarbonate, sodium hydroxide, ammonia, sodium methoxide or another base, preferably in the form of its salt. If the polyorganosiloxane contains Si—H groups, washing is preferably carried out with neutral water and not with basic water, in order to avoid the elimination of elemental hydrogen.
- insoluble solids have formed in the silicone phase, they are removed by filtration through suitable filter media before the distillation.
- Liquid, optionally highly viscous or solid compositions are obtained via the process according to the invention.
- compositions according to the invention are particularly suitable for use as binders for the production of shaped bodies with constant dielectric properties, in particular fiber composites.
- fiber composites One fiber composite application for which they are particularly well suited is in the manufacture of copper clad laminates
- Compositions are used, particularly for use for high temperature corrosion protection purposes.
- compositions according to the invention can also be used to protect reinforcing steel in reinforced concrete against corrosion. Corrosion-inhibiting effects in reinforced concrete are achieved both when the compositions according to the invention and compositions containing them are introduced into the concrete mixture before they are shaped and cured, and when the compositions according to the invention or compositions containing them are used , applied to the surface of the concrete after the concrete has hardened.
- compositions of the invention can also be used to manipulate other properties of compositions containing the compositions of the invention or of solids or films obtained from compositions containing the compositions of the invention, such as:
- Controlling the leveling properties of a formulation Controlling the gloss of a wet or cured film or object
- Control of mechanical properties such as flexibility, scratch resistance, elasticity, extensibility, bendability, tearing behavior, rebound behavior, hardness, density, tear propagation resistance, compression set, behavior at different temperatures, expansion coefficient, abrasion resistance and other properties such as thermal conductivity, flammability, gas permeability, resistance to Water vapor, hot air, chemicals, weathering and radiation, sterilizability, of solids or films available containing the compositions of the invention or preparation containing them, control of electrical properties, such as Dielectric dissipation factor, dielectric strength, dielectric constant, tracking resistance, arc resistance, surface resistance, specific breakdown resistance,
- Composition can be used to manipulate the properties identified above are the Production of coating materials and impregnations and coatings and coatings to be obtained from them on substrates such as metal, glass, wood, mineral substrate, synthetic and natural fibers for the production of textiles,
- compositions according to the invention can also be used in compositions with appropriate selection of the preparation components as an additive for the purpose of defoaming, flow promotion, hydrophobicization, hydrophilicization, filler and pigment dispersion, filler and pigment wetting, substrate wetting, promotion of surface smoothness, reduction of adhesion and slip resistance the surface of the cured mass obtainable from the additive preparation.
- the compositions according to the invention can be incorporated into elastomer compositions in liquid form or in hardened solid form. They can be used here for the purpose of reinforcing or improving other performance properties, such as controlling transparency, heat resistance, yellowing tendency or weathering resistance.
- the apparatuses are commercially available laboratory devices such as are commercially available from numerous device manufacturers.
- Me2 means two methyl radicals.
- PPE means polyphenylene ether
- HCl means hydrogen chloride
- viscosities are determined by rotational viscometric measurement in accordance with DIN EN ISO 3219. Unless otherwise stated, all viscosity data apply at 25°C and normal pressure of 1013 mbar.
- the refractive indices are determined in the wavelength range of visible light at 589 nm at 25°C and normal pressure of 1013 mbar in accordance with standard DIN 51423. Transmission :
- the transmission is determined by UV VIS spectroscopy.
- a suitable device is, for example, the Analytik Jena Specord 200.
- the measurement parameters used are: Range: 190 - 1100 nm Step size: 0.2 nm Integration time: 0.04 s Measurement mode: step mode.
- the first step is the reference measurement (background).
- a quartz plate attached to a sample holder (dimensions of the quartz plates: HxW approx. 6x7 cm, thickness approx. 2.3 mm) is placed in the sample beam path and measured against air.
- a quartz plate attached to the sample holder with a sample applied - layer thickness applied sample approx. 1 mm - is placed in the sample beam path and measured against air.
- the internal calculation against the background spectrum provides the transmission spectrum of the sample.
- the molecular compositions are determined using
- NS 64 or 128 (depending on the sensitivity of the
- Probehead 10mm lH/13C/15N/29Si glass-free QNP probehead
- Molecular weight distributions are determined as weight average Mw and as number average Mn using the gel permeation chromatography method (GPC or size exclusion chromatography (SEC)) with a polystyrene standard and refractive index detector (RI detector). Unless stated otherwise, THF is used as eluent and DIN 55672-1 is applied. The polydispersity is the quotient Mw/Mn.
- the glass transition temperature is determined by differential scanning calorimetry (DSC) in accordance with DIN 53765, perforated crucible, heating rate 10 K/min.
- the particle sizes were measured using the Dynamic Light Scattering (DLS) method, determining the zeta potential.
- DLS Dynamic Light Scattering
- the sample to be measured is homogenized and filled into the measuring cell without bubbles.
- the measurement takes place at 25°C after an equilibration time of 300s with high resolution and automatic measurement time setting.
- D(50) is to be understood as the volume-average particle diameter at which 50% of all measured particles have a volume-average diameter smaller than the declared value D(50).
- the dielectric properties are determined in accordance with IPC TM 6502.5.5.13 using a Keysight/Agilent E8361A network analyzer using the split-cylinder resonator method at 10 GHz.
- micro/nanostructure was characterized by light microscopy or by means of transmission electron microscopy.
- Sample preparation 1 drop of sample (undiluted) on slide; covered with coverslip
- LEICA DMRXA2 with CCD camera LEICA DFC420 (2592x1944 pixels)
- Sample preparation 1 drop of sample (dilution 1:20, adjustment necessary if necessary) on coated TEM grid; addition of a contrast agent if necessary; Drying at RT
- Example 1 Production of a preparation according to the invention by reacting a mixture of phenyltrichlorosilane, dimethylchlorosilane, vinyldimethylchlorosilane and the polyphenylene ether of the formula (X)
- the mixture is then poured into the dropping funnel.
- the mixture from the dropping funnel is evenly dosed into the stirred water reservoir within 2 hours.
- the temperature of the mixture increases exothermically.
- a small amount of gas evolution is observed, the gas being hydrochloric acid.
- the gaseous hydrochloric acid is drained from the reaction vessel and collected in an aqueous receiver. Most of the hydrochloric acid that forms immediately dissolves in the water present and forms a concentrated aqueous hydrochloric acid solution as the reaction progresses.
- the dosing speed is adjusted so that 50°C is not exceeded.
- the organic phase is dark brown and clear.
- the organic solvents are removed under reduced pressure (20 mbar) at elevated temperature (175° C.).
- the devolatilization is complete after 1 hour.
- the residual solvent content is 1300 ppm toluene.
- the product mixture obtained is by means of nuclear magnetic resonance spectroscopy (NMR) and by
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- composition is prepared from 50 g of the reaction product of this example with 75 g of a polyphenylene ether of formula (XI).
- the three compositions 1.1, 1.2 and 1.3 are hardened by adding 1% by weight, based on the mass of the preparation, of 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane to the respective preparation and mechanically in a coffee grinder mixed and ground.
- the preparation in question is placed in an aluminum dish and cured in a heating cabinet heated to 180° C. for 2 hours. A clear brown solid which is no longer soluble in toluene is obtained in each case.
- DSC the following values are obtained for the glass transition temperatures of the three cured compositions:
- the dissipation factor and the relative permittivity of the three cured compositions are determined according to IPC TM 650 2.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Example 2 Production of a preparation according to the invention by reacting a mixture of phenyltrichlorosilane, dimethylchlorosilane, vinyldimethylchlorosilane and a polyphenylene ether of the formula (X)
- Phenyltrichlorosilane 540 g (2.52 mol)
- the devolatilization from the solvent takes 1.5 hours.
- the product obtained has the following analytical properties:
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- the dissipation factor and the relative permittivity of the three cured compositions are determined according to IPC TM 650 2.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Example 3 Production of a preparation according to the invention by reacting a mixture of phenyltrichlorosilane, dimethylchlorosilane and a polyphenylene ether of the formula (X)
- the product obtained has the following analytical properties:
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- the dissipation factor and relative permittivity of the three cured compositions is determined according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Example 4 Production of a preparation according to the invention by reacting a mixture of phenyltrichlorosilane, vinyldimethylchlorosilane and the polyphenylene ether of the formula (X)
- Demineralized water as template 1198.8 g vinyldimethylchlorosilane: 30 g (0.25 mol)
- the devolatilization from the solvent takes 1.5 hours.
- the product obtained has the following analytical properties:
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- the dissipation factor and relative permittivity of the three cured compositions is determined according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Example 5 Production of a preparation according to the invention by reacting a mixture of phenyltrichlorosilane, vinyldimethylchlorosilane and 2,6-dimethylphenol.
- Phenyltrichlorosilane 540 g (2.52 mol)
- the devolatilization from the solvent takes 1.5 hours.
- the product obtained has the following analytical properties:
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the 2,6-dimethylphenol radical which results from 2,6-dimethylphenol by abstraction of the phenolic H atom and addition to a silicon atom.
- a total of 1.37% by weight of silanol groups are present, as can be deduced from the 1 H-NMR spectrum.
- compositions obtained are yellowish solids which are clear in thin layers and which, according to the TEM investigation, are completely homogeneous.
- the dissipation factor and relative permittivity of the three cured compositions is determined according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Comparative Example 1 Production of a preparation not according to the invention by reacting a mixture of methyltrichlorosilane and vinyldimethylchlorosilane and the polyphenylene ether of the formula (X).
- Demineralized water as template 1198.8 g vinyldimethylchlorosilane: 30 g (0.25 mol)
- the product obtained has the following analytical properties:
- the product obtained is brown, but does not give clear films, instead cloudy, opaque films are obtained.
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- two hydrogen atoms can be abstracted from the doubly OH-terminated polyphenylene ether (X).
- this may be considered unlikely, so that preferably or exclusively only one phenolic hydrogen atom is used remainder formation is abstracted.
- the same situation should apply to all examples described here and should not be limited to this specific example.
- compositions obtained are brown solids, although cloudy and not clear in thin layers, forming clearly distinguishable silicone domains and areas of organic polymer according to TEM examination.
- the compositions are thus inhomogeneous due to the incompatibility of the components mixed with one another.
- the dissipation factor and relative permittivity of the three cured compositions is determined according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- a solution of 86.00 g of the polyphenylene ether (X) in 462.75 g of toluene is rapidly metered into the mixture obtained in the reaction vessel.
- 111.06 g of deionized water are metered into this template over the course of 35 minutes.
- the temperature of the mixture in the reaction vessel rises from 23.9°C to 50.8°C.
- an additional 666.36 g of water is added over 5 minutes, the formulation is mixed well, and then 1 L of acetone is added. After mixing again, the stirring is stopped. After standing for one hour, the lower phase is separated off. It consists of hydrochloric acid water, ethanol and acetone.
- the product mixture obtained is by means of nuclear magnetic resonance spectroscopy (NMR) and by
- the residual solvent content is 1243 ppm toluene.
- the product obtained is brown, but does not give clear films, instead cloudy, opaque films are obtained.
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen, an ethyl radical or the polyphenylene ether radical which results from the Polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- compositions obtained are brown solids, although cloudy and not clear in thin layers, forming clearly distinguishable silicone domains and areas of organic polymer according to TEM examination.
- the compositions are thus inhomogeneous due to the incompatibility of the components mixed with one another.
- the condensation is a slow process in which the ethoxy groups present react only slowly, so that not all the ethoxy groups present react completely within the specified curing time of 2 h.
- the risk of further ethanol splitting off at a later date is therefore unavoidable.
- the dissipation factor and relative permittivity of the three cured compositions is determined according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Phenyltrichlorosilane 448.44g (2.12 mol)
- the product mixture obtained is by means of nuclear magnetic resonance spectroscopy (NMR) and by
- the residual solvent content is 873 ppm toluene.
- Ethoxy groups are present in an amount of 5.1% by weight as determined by 1 H NMR.
- the product obtained is brown and gives clear, thin and transparent films.
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen, an ethyl radical or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- the total amount of silanol groups was determined by 1 H-NMR to be 3.21% by weight.
- compositions obtained are brown solids, clear in thin layers, which do not form distinguishable silicone domains and organic polymer domains by TEM examination.
- the compositions are thus homogeneous.
- the dissipation factor and the relative permittivity of the three cured compositions are determined according to IPC TM 650 2.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- Production example 3 in US 2018/0220530 contains no information on the relative amounts of the raw materials used. Thus, this production example, like all other production examples of US 2018/0220530, also does not indicate a specific resin, but merely specifies a general procedure. It should be noted here that the production examples of US 2018/0220530 always refer to triethylphenyl silicate as the raw material, which is metered in drop by drop. Since T units are always formed in the resin from the triethylphenyl silicate units, this designation is obviously incorrect.
- Aqueous hydrochloric acid, 20%: 0.916 g corresponds to 400 ppm HCl for the amount of silicone used and is a conventional amount of HCl known to those skilled in the art from numerous prior art as a condensation catalyst for such condensation tasks in a stirred reactor.
- the product mixture obtained is by means of nuclear magnetic resonance spectroscopy (NMR) and by
- the product obtained is colorless and clear.
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R denotes either hydrogen or an ethyl radical.
- the amount of silanol groups is 3.1 percent by weight.
- the proportion of phenyl radicals in the Si—C-bonded hydrocarbon radicals is 24.5 mol %, the proportion of vinyl radicals is 14.0 mol % and the proportion of methyl radicals is 61.5 mol %.
- compositions with the polyphenylene ethers of the formulas (X) and (XI) are prepared from the reaction product and, following the nomenclature logic of Example 1, are referred to as VB 4.2 and VB 4.3.
- compositions are brown solids, cloudy and opaque in thin layers, which, by TEM examination, form clearly distinguishable silicone domains and discrete regions of polyorganosiloxane and organic polymer.
- the compositions are thus inhomogeneous.
- DSC the following values are obtained for the glass transition temperatures of the three cured compositions:
- the dissipation factor and relative permittivity of the neat resin and the two cured compositions are determined according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- the moldings from the compositions VB 4.2 and VB 4.3, which were used to determine the dielectric properties, are placed in a climatic chamber with a fixed climate of 23° C. and 80% relative humidity and their dielectric properties after 8, 16 and 32 weeks remeasured, the dielectric loss factor and the relative permittivity according to IPC TM 6502.5.5.13 using a Keysight Agilent E8361A Network Analyzers at 10 GHz. The following values were obtained:
- the shaped bodies do not have constant dielectric properties over the course of the test.
- the observed increase in dissipation factors is significant. This is an expression of both the microporosity caused by the incompatibility of the polyorganosiloxane with the polyphenylene ethers within the test specimens and the lack of hydrolytic stability due to the alkoxy groups present under the selected test conditions.
- the product obtained has the following analytical properties:
- the molar composition of the silicon-containing portion of the preparation is:
- the radical R is either hydrogen or the polyphenylene ether radical which results from the polyphenylene ether (X) by abstraction of the phenolic H atom and addition to a silicon atom.
- a total of 1.54 percent by weight of silanol groups are present according to 1 H-NMR.
- the dissipation factor and the relative permittivity of the three cured compositions are determined according to IPC TM 650 2.5.5.13 using a Keysight Agilent E8361A Network Analyzer. You get the following values:
- the moldings that were produced to determine the dielectric properties are placed in a climate chamber with a fixed climate of 23 ° C and 80% relative humidity and measured their dielectric properties after 8, 16 and 32 weeks, with the dielectric
- Dissipation factor and the dielectric constant were determined according to IPC TM 650 2.5.5.13 using a Keysight Agilent E8361A Network Analyzer at 10 GHz. The following values were obtained:
- the moldings VB 4.4, VB 4.5 and VB 4.6, produced according to example 1 according to the invention have constant dielectric properties over the test period
- the dielectric properties of the moldings VB 4.2 and VB 4.3 change with a polyorganosiloxane according to production example 3 from US 2018/0220350 towards higher values.
- the increase in the dielectric loss factor is significant. This is an expression of the lack of hydrolytic stability and the lack of compatibility under the selected conditions.
- the two molded bodies are placed in a climatic chamber with a fixed climate of 23° C. and 80% relative humidity and their dielectric properties are measured after 8, 16 and 32 weeks, the dielectric dissipation factor and the permittivity according to IPC TM 650 2.5.5.13 using a Keysight Agilent E8361A Network Analyzer at 10 GHz. The following values were obtained:
- the shaped body according to the example according to the invention has constant dielectric properties over the test period, the dielectric properties of the shaped body according to US 2020/028575 change towards higher values.
- the increase in the dielectric loss factor is significant. This is an expression of the lack of hydrolytic stability under the selected test conditions.
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Abstract
L'invention concerne : un procédé de production de compositions, procédé dans lequel a) des composés choisis parmi des éthers de polyphénylène d'homopolymère ou de copolymère à terminaison hydroxy et des phénols sont mis à réagir avec b) un chlorosilane représenté par la formule (I), seul ou mélangé à un disiloxane de formule (IV) R1 aR2 bSiCl4 -a-b (I), [R1 (3-b)R2 bSi]2O (IV), en présence d'eau et de solvant, R1, R2, a et b ayant les significations indiquées dans la revendication 1 ; des compositions qui peuvent être produites selon le procédé ; et l'emploi de des compositions en tant que liants pour la production de corps moulés ayant des propriétés diélectriques constantes.
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PCT/EP2021/065191 WO2022258140A1 (fr) | 2021-06-07 | 2021-06-07 | Compositions contenant des polyorganosiloxanes ayant des groupes éther de polyphénylène |
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EP21732824.4A Pending EP4352130A1 (fr) | 2021-06-07 | 2021-06-07 | Compositions contenant des polyorganosiloxanes ayant des groupes éther de polyphénylène |
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EP (1) | EP4352130A1 (fr) |
JP (1) | JP2024520759A (fr) |
KR (1) | KR20240017938A (fr) |
CN (1) | CN117794982A (fr) |
WO (1) | WO2022258140A1 (fr) |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
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NL295748A (fr) | 1962-07-24 | |||
US3737479A (en) | 1970-08-19 | 1973-06-05 | Gen Electric | Composition of polyorganosiloxane and polyphenylene oxide |
US3960985A (en) | 1974-02-08 | 1976-06-01 | General Electric Company | Polypheylene ether-resin compositions with organopolyiloxanes having silicon-H-bonds |
US4814392A (en) | 1987-11-25 | 1989-03-21 | General Electric Company | Silicone-polyarylene ether block copolymers, and method for making |
JP2542152B2 (ja) | 1991-10-30 | 1996-10-09 | ゼネラル・エレクトリック・カンパニイ | 熱可塑性シリコ―ン−ポリフェニレンエ―テルブロック共重合体の製造法 |
JPH1045770A (ja) | 1996-07-29 | 1998-02-17 | Toray Dow Corning Silicone Co Ltd | ヘキサメチルシクロトリシロキサンの分離方法 |
DE19947832A1 (de) | 1998-10-07 | 2000-04-13 | Sumitomo Chemical Co | Polyphenylenetherharzmasse |
CN100526382C (zh) | 2001-01-24 | 2009-08-12 | 旭化成化学株式会社 | 含有硅化合物的聚苯醚基树脂组合物 |
CN105086417B (zh) | 2014-05-06 | 2017-09-12 | 广东生益科技股份有限公司 | 一种树脂组合物及其在高频电路板中的应用 |
DE102015214502A1 (de) | 2015-07-30 | 2017-02-02 | Wacker Chemie Ag | Verfahren zur Herstellung von Organopolysiloxanen |
US9930598B2 (en) | 2015-08-21 | 2018-03-27 | Samsung Electronics Co., Ltd. | Method and apparatus for offload operation of the idle mode in a cellular device |
CN106609039B (zh) | 2015-10-21 | 2019-09-13 | 广东生益科技股份有限公司 | 一种聚苯醚树脂组合物及其在高频电路基板中的应用 |
CN106609030B (zh) | 2015-10-21 | 2018-12-25 | 广东生益科技股份有限公司 | 一种聚苯醚树脂组合物及其在高频电路基板中的应用 |
CN106916293B (zh) | 2015-12-25 | 2019-07-26 | 广东生益科技股份有限公司 | 一种有机硅改性的聚苯醚树脂、制备方法及用途 |
WO2018075962A1 (fr) | 2016-10-21 | 2018-04-26 | Viasat, Inc. | Communications à formation de faisceau basées au sol utilisant des liaisons de connexion spatialement multiplexées synchronisées mutuellement |
CN109840047A (zh) | 2017-11-27 | 2019-06-04 | 华为技术有限公司 | 一种降低读延时的方法及装置 |
GB2596696B (en) | 2019-05-23 | 2023-08-30 | Rogers Corp | Low loss, composite layer and a composition for forming the same |
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2021
- 2021-06-07 CN CN202180101394.8A patent/CN117794982A/zh active Pending
- 2021-06-07 JP JP2023575413A patent/JP2024520759A/ja active Pending
- 2021-06-07 KR KR1020247000492A patent/KR20240017938A/ko unknown
- 2021-06-07 EP EP21732824.4A patent/EP4352130A1/fr active Pending
- 2021-06-07 WO PCT/EP2021/065191 patent/WO2022258140A1/fr active Application Filing
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WO2022258140A1 (fr) | 2022-12-15 |
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