JP2020059851A - ポリ(アリーレンエーテル)コポリマー - Google Patents
ポリ(アリーレンエーテル)コポリマー Download PDFInfo
- Publication number
- JP2020059851A JP2020059851A JP2019185241A JP2019185241A JP2020059851A JP 2020059851 A JP2020059851 A JP 2020059851A JP 2019185241 A JP2019185241 A JP 2019185241A JP 2019185241 A JP2019185241 A JP 2019185241A JP 2020059851 A JP2020059851 A JP 2020059851A
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- JP
- Japan
- Prior art keywords
- poly
- arylene ether
- copolymer
- resin
- bis
- 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
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- -1 Poly(arylene ether Chemical compound 0.000 title claims abstract description 216
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 152
- 229920001577 copolymer Polymers 0.000 title claims abstract description 147
- 239000000203 mixture Substances 0.000 claims abstract description 120
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 105
- 239000000178 monomer Substances 0.000 claims abstract description 48
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims abstract description 39
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 22
- 230000001590 oxidative effect Effects 0.000 claims abstract description 20
- 125000003277 amino group Chemical group 0.000 claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 claims abstract description 12
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims description 81
- 229920005989 resin Polymers 0.000 claims description 79
- 239000011347 resin Substances 0.000 claims description 79
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 claims description 50
- 239000002904 solvent Substances 0.000 claims description 44
- 239000003054 catalyst Substances 0.000 claims description 40
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 32
- 150000001412 amines Chemical class 0.000 claims description 30
- 229920001187 thermosetting polymer Polymers 0.000 claims description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 239000003822 epoxy resin Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 229920000647 polyepoxide Polymers 0.000 claims description 19
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 239000004643 cyanate ester Substances 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 claims description 12
- 239000010949 copper Substances 0.000 claims description 12
- 238000005227 gel permeation chromatography Methods 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 11
- 229910052802 copper Inorganic materials 0.000 claims description 11
- 239000001294 propane Substances 0.000 claims description 10
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 claims description 7
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical compound CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 claims description 7
- 239000002131 composite material Substances 0.000 claims description 7
- XSTITJMSUGCZDH-UHFFFAOYSA-N 4-(4-hydroxy-2,6-dimethylphenyl)-3,5-dimethylphenol Chemical compound CC1=CC(O)=CC(C)=C1C1=C(C)C=C(O)C=C1C XSTITJMSUGCZDH-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 4
- KGHYGBGIWLNFAV-UHFFFAOYSA-N n,n'-ditert-butylethane-1,2-diamine Chemical compound CC(C)(C)NCCNC(C)(C)C KGHYGBGIWLNFAV-UHFFFAOYSA-N 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 239000006260 foam Substances 0.000 claims description 3
- 239000010410 layer Substances 0.000 claims description 3
- 239000000565 sealant Substances 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- 239000002775 capsule Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 28
- 229920003192 poly(bis maleimide) Polymers 0.000 description 22
- 229910052757 nitrogen Inorganic materials 0.000 description 21
- 229920002857 polybutadiene Polymers 0.000 description 19
- 239000005062 Polybutadiene Substances 0.000 description 18
- 150000002989 phenols Chemical class 0.000 description 17
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 16
- 238000006116 polymerization reaction Methods 0.000 description 16
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 14
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 229930185605 Bisphenol Natural products 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 11
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 10
- 239000003352 sequestering agent Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000012296 anti-solvent Substances 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 230000002829 reductive effect Effects 0.000 description 7
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 6
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical group C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- PVFQHGDIOXNKIC-UHFFFAOYSA-N 4-[2-[3-[2-(4-hydroxyphenyl)propan-2-yl]phenyl]propan-2-yl]phenol Chemical compound C=1C=CC(C(C)(C)C=2C=CC(O)=CC=2)=CC=1C(C)(C)C1=CC=C(O)C=C1 PVFQHGDIOXNKIC-UHFFFAOYSA-N 0.000 description 6
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 6
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
- 229910052794 bromium Inorganic materials 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 6
- 238000012546 transfer Methods 0.000 description 6
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical group OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- GIXXQTYGFOHYPT-UHFFFAOYSA-N Bisphenol P Chemical compound C=1C=C(C(C)(C)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 GIXXQTYGFOHYPT-UHFFFAOYSA-N 0.000 description 5
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 150000001983 dialkylethers Chemical class 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 150000008442 polyphenolic compounds Chemical class 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 239000005060 rubber Substances 0.000 description 5
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 4
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 4
- YMTYZTXUZLQUSF-UHFFFAOYSA-N 3,3'-Dimethylbisphenol A Chemical compound C1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=CC=2)=C1 YMTYZTXUZLQUSF-UHFFFAOYSA-N 0.000 description 4
- WOCGGVRGNIEDSZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical compound C=1C=C(O)C(CC=C)=CC=1C(C)(C)C1=CC=C(O)C(CC=C)=C1 WOCGGVRGNIEDSZ-UHFFFAOYSA-N 0.000 description 4
- WFCQTAXSWSWIHS-UHFFFAOYSA-N 4-[bis(4-hydroxyphenyl)methyl]phenol Chemical class C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 WFCQTAXSWSWIHS-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 238000007792 addition Methods 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 150000005130 benzoxazines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 4
- 150000001913 cyanates Chemical class 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- MGFYIUFZLHCRTH-UHFFFAOYSA-N nitrilotriacetic acid Chemical group OC(=O)CN(CC(O)=O)CC(O)=O MGFYIUFZLHCRTH-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DEQUKPCANKRTPZ-UHFFFAOYSA-N (2,3-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1O DEQUKPCANKRTPZ-UHFFFAOYSA-N 0.000 description 3
- CNQBVZJAOPPVJH-UHFFFAOYSA-N 1',1',3,3-tetramethyl-1,3'-spirobi[2h-indene]-5,5'-diol Chemical compound C12=CC(O)=CC=C2C(C)(C)CC11C2=CC=C(O)C=C2C(C)(C)C1 CNQBVZJAOPPVJH-UHFFFAOYSA-N 0.000 description 3
- SICLLPHPVFCNTJ-UHFFFAOYSA-N 1,1,1',1'-tetramethyl-3,3'-spirobi[2h-indene]-5,5'-diol Chemical compound C12=CC(O)=CC=C2C(C)(C)CC11C2=CC(O)=CC=C2C(C)(C)C1 SICLLPHPVFCNTJ-UHFFFAOYSA-N 0.000 description 3
- GOPGGLXYHLDHLG-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3,3-dimethyl-1,2-dihydroinden-5-ol Chemical compound C12=CC=C(O)C=C2C(C)(C)CC1C1=CC=C(O)C=C1 GOPGGLXYHLDHLG-UHFFFAOYSA-N 0.000 description 3
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 3
- LLOXZCFOAUCDAE-UHFFFAOYSA-N 2-diphenylphosphorylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(P(=O)(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 LLOXZCFOAUCDAE-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 3
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 3
- DVJDHNJKCNMAED-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)butyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(CCC)C1=CC=C(O)C=C1 DVJDHNJKCNMAED-UHFFFAOYSA-N 0.000 description 3
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 description 3
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- DSROZUMNVRXZNO-UHFFFAOYSA-K tris[(1-naphthalen-1-yl-3-phenylnaphthalen-2-yl)oxy]alumane Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C=1O[Al](OC=1C(=C2C=CC=CC2=CC=1C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)OC(C(=C1C=CC=CC1=C1)C=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 DSROZUMNVRXZNO-UHFFFAOYSA-K 0.000 description 1
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- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
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Abstract
Description
1,2−ビスマレイミドエタン、1,6−ビスマレイミドヘキサン、1,3−ビスマレイミドベンゼン、1,4−ビスマレイミドベンゼン、2,4−ビスマレイミドトルエン、4,4’−ビスマレイミドジフェニルメタン、4,4’−ビスマレイミドジフェニルエーテル、3,3’−ビスマレイミドジフェニルスルホン、4,4’−ビスマレイミドジフェニルスルホン、4,4’−ビスマレイミドジシクロヘキシルメタン、3,5−ビス(4−マレイミドフェニル)ピリジン、2,6−ビスマレイミドピリジン、1,3−ビス(マレイミドメチル)シクロヘキサン、1,3−ビス(マレイミドメチル)ベンゼン、1,1−ビス(4−マレイミドフェニル)シクロヘキサン、1,3−ビス(ジクロロマレイミド)ベンゼン、4,4’−ビス(シトラコンイミド)ジフェニルメタン、2,2−ビス(4−マレイミドフェニル)プロパン、1−フェニル−1,1−ビス(4−マレイミドフェニル)エタン、N,N−ビス(4−マレイミドフェニル)トルエン、3,5−ビスマレイミド−1,2,4−トリアゾールN,N’−エチレンビスマレイミド、N,N’−ヘキサメチレンビスマレイミド、N,N’−m−フェニレンビスマレイミド、N,N’−p−フェニレンビスマレイミド、N,N’−4,4’−ジフェニルメタンビスマレイミド、N,N’−4,4’−ジフェニルエーテルビスマレイミド、N,N’−4,4’−ジフェニルスルホンビスマレイミド、N,N’−4,4’−ジシクロヘキシルメタンビスマレイミド、N,N’−α,α’−4,4’−ジメチレンシクロヘキサンビスマレイミド、N,N’−m−メタキシレンビスマレイミド、N,N’−4,4’−ジフェニルシクロヘキサンビスマレイミド、およびN,N’−メチレンビス(3−クロロ−p−フェニレン)ビスマレイミドに加えて、Bargainらの米国特許第3,562,223号明細書、並びにStenzenbergerの米国特許第4,211,860号明細書および米国特許第4,211,861号明細書に開示されているマレイミド樹脂が挙げられ得る。ビスマレイミド樹脂は、例えば、Sautersらの米国特許第3,018,290号明細書に記載されているような、当分野で既知の方法によって調製できる。一部の実施形態では、ビスマレイミド樹脂はN,N’−4,4’−ジフェニルメタンビスマレイミドである。
Claims (15)
- 一価フェノールと二価フェノールとを含むモノマーの酸化共重合の生成物であり、二価フェノールが下記式のものであり、アミン基が0.1質量%以下組み込まれていることを特徴とするポリ(アリーレンエーテル)コポリマー。
- 前記一価フェノールが、2,6−ジメチルフェノール、2,3,6−トリメチルフェノール、またはそれらの組み合わせを含み、二価フェノールは2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)プロパンを含む請求項1に記載のポリ(アリーレンエーテル)コポリマー。
- 前記ポリ(アリーレンエーテル)コポリマーが、数平均分子量が500〜2,500g/mol、質量平均分子量が1,000〜6,000g/molであり、数平均分子量および質量平均分子量はゲル浸透クロマトグラフィーによって決定されるものである請求項1または2に記載のポリ(アリーレンエーテル)コポリマー。
- 前記酸化共重合がジ−n−ブチルアミンを含む触媒組成物の存在下であり、ポリ(アリーレンエーテル)コポリマーには、ジブチルアミン基が0.1質量%以下組み込まれており、好ましくはジブチルアミン基が0.01〜0.1質量%組み込まれている請求項1〜3のいずれか1項に記載のポリ(アリーレンエーテル)コポリマー。
- 前記酸化共重合がジ−n−ブチルアミンを含まない触媒組成物の存在下であり、ポリ(アリーレンエーテル)コポリマーには、ジブチルアミン基が組み込まれていない請求項1〜4のいずれか1項に記載のポリ(アリーレンエーテル)コポリマー。
- 前記ポリ(アリーレンエーテル)コポリマーのクロロホルム中25℃で測定した固有粘度が0.04〜0.15dL/gであり、好ましくは0.06〜0.1dL/g、より好ましくは0.075〜0.090dL/gである請求項1〜5のいずれか1項に記載のポリ(アリーレンエーテル)コポリマー。
- 前記ポリ(アリーレンエーテル)コポリマーが、分子当たり平均1.8〜2個のヒドロキシル基を有する請求項1〜6のいずれか1項に記載のポリ(アリーレンエーテル)コポリマー。
- 金属源、好ましくは銅源と;
二級アルキレンジアミンリガンド、好ましくはN,N’−ジ−tert−ブチル−1,2−エチレンジアミンを0.18〜0.40質量%と;
二級モノアミン、好ましくはジ−n−ブチルアミンを0〜0.2質量%と;
第三級モノアミン、好ましくはジメチルブチルアミンと;
を含む触媒組成物の存在下で、一価フェノールと二価フェノールとを溶媒中で酸化共重合させて、ポリ(アリーレンエーテル)コポリマー形成するステップを含み、
前記触媒組成物の各成分の質量%は前記一価フェノールと前記二価フェノールとの合計質量に対してのものであることを特徴とするポリ(アリーレンエーテル)コポリマーの製造方法。 - 前記触媒組成物が、ジ−n−ブチルアミンを0.05〜0.15質量%含み、前記ポリ(アリーレンエーテル)コポリマーにはジブチルアミン基が0.01〜0.1質量%組み込まれている請求項8に記載のポリ(アリーレンエーテル)コポリマーの製造方法。
- 前記触媒組成物が二級モノアミンを含まず、ポリ(アリーレンエーテル)コポリマーにはアミン基が組み込まれていない請求項8に記載のポリ(アリーレンエーテル)コポリマーの製造方法。
- 数平均分子量が500〜2,500g/mol、質量平均分子量が1,000〜6,000g/molであり、数平均分子量および質量平均分子量はゲル浸透クロマトグラフィーによって決定されるものであり;
クロロホルム中25℃で測定した固有粘度が0.04〜0.15dL/gであり;
組み込まれたジブチルアミン基が0.1質量%以下であり;
3,3’,5,5’−テトラメチル−4,4’−ビフェノール由来の単位を0.5〜1.5質量%有し;
好ましくは、2,6−ジメチルフェノールおよび2,2−ビス(3,5−ジメチル−4−ヒドロキシフェニル)プロパン由来の繰り返し単位を含むことを特徴とする、請求項8〜10のいずれか1項に記載の方法によって製造されたポリ(アリーレンエーテル)コポリマー。 - 請求項1〜7のいずれかに記載のポリ(アリーレンエーテル)コポリマーと;
補助の硬化性樹脂、硬化性不飽和モノマー組成物、またはそれらの両方と;
任意選択的に、硬化促進剤と;を含み、
好ましくは、前記補助の硬化性樹脂は、エポキシ樹脂、シアネートエステル樹脂、マレイミド樹脂、ベンゾキサジン樹脂、ビニルベンジルエーテル樹脂、アリールシクロブテン樹脂、ペルフルオロビニルエーテル樹脂、硬化性ビニル官能性を有するオリゴマーもしくはポリマー、またはそれらの組み合わせを含み、硬化性不飽和モノマーを含む組成物単官能性スチレン化合物、単官能性(メタ)アクリル酸化合物、多官能性アリル化合物、多官能性(メタ)アクリレート、多官能性(メタ)アクリルアミド、多官能性スチレン化合物、またはそれらの組み合わせを含むことを特徴とする硬化性組成物。 - 請求項1〜7のいずれかに記載のポリ(アリーレンエーテル)コポリマーと、
エポキシ樹脂、シアネートエステル樹脂、またはそれらの組み合わせと;
任意選択的に、硬化促進剤と、を含み、好ましくは、前記硬化促進剤は無水物またはアミンを含む請求項12に記載の硬化性組成物。 - 請求項12または13に記載の硬化性組成物の硬化した生成物を含む熱硬化組成物。
- 請求項14に記載の熱硬化組成物を含み、好ましくは、複合材、発泡体、繊維、層、コーティング、カプセルの材料、接着剤、封止剤、成形品、プリプレグ、ケーシング、または前記の少なくとも1つを含む組み合わせの形態である物品。
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CN111004385A (zh) | 2020-04-14 |
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