JP2019194312A - フェニレンエーテルオリゴマー、フェニレンエーテルオリゴマーを含む硬化性組成物、およびそれか得られる熱硬化組成物 - Google Patents
フェニレンエーテルオリゴマー、フェニレンエーテルオリゴマーを含む硬化性組成物、およびそれか得られる熱硬化組成物 Download PDFInfo
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- JP2019194312A JP2019194312A JP2019080472A JP2019080472A JP2019194312A JP 2019194312 A JP2019194312 A JP 2019194312A JP 2019080472 A JP2019080472 A JP 2019080472A JP 2019080472 A JP2019080472 A JP 2019080472A JP 2019194312 A JP2019194312 A JP 2019194312A
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- Prior art keywords
- phenylene ether
- group
- ether oligomer
- resin
- oligomer
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 128
- OMIHGPLIXGGMJB-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-1,3,5-triene Chemical compound C1=CC=C2OC2=C1 OMIHGPLIXGGMJB-UHFFFAOYSA-N 0.000 title claims abstract description 115
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 46
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims abstract description 15
- 125000003277 amino group Chemical group 0.000 claims abstract description 14
- 150000008064 anhydrides Chemical group 0.000 claims abstract description 13
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical compound OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims abstract description 10
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims abstract description 9
- 229920005989 resin Polymers 0.000 claims description 85
- 239000011347 resin Substances 0.000 claims description 85
- -1 polysiloxane Polymers 0.000 claims description 66
- 239000000178 monomer Substances 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000002131 composite material Substances 0.000 claims description 24
- 229920001296 polysiloxane Polymers 0.000 claims description 20
- 229920000647 polyepoxide Polymers 0.000 claims description 19
- 239000003822 epoxy resin Substances 0.000 claims description 18
- CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229920000642 polymer Polymers 0.000 claims description 14
- 239000004643 cyanate ester Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- AZDCYKCDXXPQIK-UHFFFAOYSA-N ethenoxymethylbenzene Chemical compound C=COCC1=CC=CC=C1 AZDCYKCDXXPQIK-UHFFFAOYSA-N 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 238000006116 polymerization reaction Methods 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- YCUALLYXPZGZFN-UHFFFAOYSA-N 2-cyclohexyl-6-methylphenol Chemical compound CC1=CC=CC(C2CCCCC2)=C1O YCUALLYXPZGZFN-UHFFFAOYSA-N 0.000 claims description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 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
- 239000000835 fiber Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 239000006260 foam Substances 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 5
- 239000000853 adhesive Substances 0.000 claims description 5
- 230000001070 adhesive effect Effects 0.000 claims description 5
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- 150000008117 polysulfides Polymers 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 239000008393 encapsulating agent Substances 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 4
- 229920001568 phenolic resin Polymers 0.000 claims description 4
- 229920002647 polyamide Polymers 0.000 claims description 4
- 239000000565 sealant Substances 0.000 claims description 4
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 3
- 238000005227 gel permeation chromatography Methods 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- 238000010276 construction Methods 0.000 claims 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 16
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 31
- 229910052757 nitrogen Inorganic materials 0.000 description 29
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 150000001412 amines Chemical class 0.000 description 22
- 229920003192 poly(bis maleimide) Polymers 0.000 description 22
- 229920002857 polybutadiene Polymers 0.000 description 22
- 239000000243 solution Substances 0.000 description 19
- 230000003014 reinforcing effect Effects 0.000 description 18
- 239000005062 Polybutadiene Substances 0.000 description 17
- 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 17
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 15
- 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 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 14
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229930185605 Bisphenol Natural products 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 229920001400 block copolymer Polymers 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000011256 inorganic filler Substances 0.000 description 12
- 229910003475 inorganic filler Inorganic materials 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 230000001588 bifunctional effect Effects 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 125000000524 functional group Chemical group 0.000 description 10
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 10
- 235000013824 polyphenols Nutrition 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 239000003365 glass fiber Substances 0.000 description 9
- 150000002989 phenols Chemical class 0.000 description 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical class OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 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 8
- 239000001301 oxygen Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 238000012545 processing Methods 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical class OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- 239000011521 glass Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 239000000523 sample Substances 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
- FAXWFCTVSHEODL-UHFFFAOYSA-N 2,4-dibromophenol Chemical compound OC1=CC=C(Br)C=C1Br FAXWFCTVSHEODL-UHFFFAOYSA-N 0.000 description 6
- 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 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
- 150000001983 dialkylethers Chemical class 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000003446 ligand Substances 0.000 description 6
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- 239000000047 product Substances 0.000 description 6
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- 239000000126 substance Substances 0.000 description 6
- 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 125000005263 alkylenediamine group Chemical group 0.000 description 5
- IMHDGJOMLMDPJN-UHFFFAOYSA-N biphenyl-2,2'-diol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1O IMHDGJOMLMDPJN-UHFFFAOYSA-N 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 150000001913 cyanates Chemical class 0.000 description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 5
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- 239000005060 rubber Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- SLBOQBILGNEPEB-UHFFFAOYSA-N 1-chloroprop-2-enylbenzene Chemical compound C=CC(Cl)C1=CC=CC=C1 SLBOQBILGNEPEB-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
- 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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 4
- 150000001345 alkine derivatives Chemical group 0.000 description 4
- 150000004982 aromatic amines Chemical class 0.000 description 4
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- 238000006243 chemical reaction Methods 0.000 description 4
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- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000004122 cyclic group Chemical group 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
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 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 description 4
- 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 4
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- 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
- 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
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-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
- 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 3
- 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 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
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Classifications
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- 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
-
- 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
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
- C08G81/02—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers at least one of the polymers being obtained by reactions involving only carbon-to-carbon unsaturated bonds
- C08G81/024—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G
- C08G81/025—Block or graft polymers containing sequences of polymers of C08C or C08F and of polymers of C08G containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- 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
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4087—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the catalyst used
-
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Abstract
Description
を含む構造を有する]を有する二官能性フェニレンエーテルオリゴマーを含む。
を有する」を有する、複数の繰り返し単位を含むことができる。したがって、いくつかの実施形態において、ヒドロキシアリール末端ポリシロキサンは、構造
を有する二官能性フェニレンエーテルオリゴマー−ポリシロキサンブロックコポリマーであってよい。非常に特定の実施形態において、上記式中のRは、ビニルベンジル基であってよい。
(Rd)2N−Rc−N(Rd)2
[式中、Rcは、置換または非置換二価残基であり;各Rdは、独立して水素またはC1〜C8アルキルである]を有するものが挙げられる。いくつかの実施例において、上記式中、2つまたは3つの脂肪族炭素原子は、2つのジアミン窒素原子間で最も接近した連鎖を形成する。特定のアルキレンジアミン配位子としては、Rcがジメチレン(−CH2CH2−)またはトリメチレン(−CH2CH2CH2−)であるものが挙げられる。Rdは、独立して、水素、メチル、プロピル、イソプロピル、ブチル、またはC4〜C8α−tert−アルキル基であり得る。アルキレンジアミン配位子の例としては、N,N,N’,N’テトラメチルエチレンジアミン(TMED)、N,N’−ジ−tert−ブチルエチレンジアミン(DBEDA)、N,N,N’,N’−テトラメチル−1,3−ジアミノプロパン(TMPD)、N−メチル−1,3−ジアミノプロパン、N,N’−ジメチル−1,3−ジアミノプロパン、N,N,N’−ジメチル−1,3−ジアミノプロパン、N−エチル−1,3−ジアミノプロパン、N−メチル−1,4−ジアミノブタン、N,N’−トリメチル−1,4−ジアミノブタン、N,N,N’−トリメチル−1,4−ジアミノブタン、N,N,N’,N’−テトラメチル−1,4−ジアミノブタン、N,N,N’,N’−テトラメチル−1,5−ジアミノペンタン、またはこれらの組合せが挙げられる。いくつかの実施形態において、アミン配位子は、ジ−n−ブチルアミン(DBA)、N,N−ジメチルブチルアミン(DMBA)、N,N’−ジ−tert−ブチルエチレンジアミン(DBEDA)、またはこれらの組合せである。触媒は、金属イオン供給源(例えば、亜酸化銅および臭化水素酸)とアミン配位子を混合することによって、in situで調製することができる。いくつかの実施形態において、重合触媒は、銅イオン、臭化物イオン、およびN,N’−ジ−tert−ブチルエチレンジアミンを含む。
上記の合成に従ってPPE−CMPを調製した。CMP−PPEの構造を溶液NMR分光法によって確認した。NMR分析により、CMP−PPEの最終構造が、エーテル結合により主鎖に組み込まれた、2−メチル−6−シクロヘキシルフェノールおよびTMBPA基から構成されることが明らかとなった。CMP−PPEの末端基は、平均官能価が2である二官能性オリゴマーをもたらすフェノール系単位であることもNMR分析から見出された。
キシレン中の水性NaOHの存在下で3−および4−ビニルベンジルクロリドの混合物とPPE−CMPとを反応させることによって、上記の合成に従ってPPE−CMP−2VBを調製した。単離したPPE−CMP−2VBの最終構造を溶液NMR分光法によって確認した。PPE−CMP−2VBのNMRスペクトルにおいて、PPE−CMPの末端基芳香族プロトンに対応するピークの消失、ならびにビニルベンジル基プロトンに対応する新しいピークおよびビニルベンジル末端基に結合したCMP基の芳香族プロトンに対応する新しいピークの形成により、ビニルベンジル官能化二官能性PPE−CMP−2VBの構造を確認した。
上記のCMP−PPEオリゴマーとの比較のために、以下の手順に従ってCP−PPEオリゴマーを合成した。トルエン(168グラム)、CP(49グラム)、TMBPA(6.40グラム)、DMBA(1.68グラム)、DBA(0.56グラム)、ならびに0.088グラムのDBEDA、0.047グラムのPTC−1、および0.15グラムのトルエンの混合物を、500ミリリットル発泡重合容器に充填し、窒素下で撹拌した。触媒溶液(0.42グラム;0.03グラムのCu2Oおよび0.39グラムの(48%)HBr)を上記の反応混合物に添加した。触媒溶液の添加後、酸素流れを開始した。15分で25℃から39.4℃へと温度を上昇させ、70分の時点で温度を48.9℃に上げた。酸素流れを130分間維持し、その時点で流れを停止し、1.0グラムのNTAおよび6.0グラムの水を反応混合物に添加した。得られた混合物を60℃で2時間撹拌した。遠心分離により層を分離し、メタノール中への析出により軽い相を単離した。析出した粒子を濾過し、真空オーブン内で110℃において窒素下で一晩乾燥させた後、分析した。
Claims (15)
- 請求項1に記載のフェニレンエーテルオリゴマーであって、ポリスチレン標準に対するゲル透過クロマトグラフィーによって決定された、600〜5,000グラム/モルの数平均分子量を有することを特徴とするフェニレンエーテルオリゴマー。
- 請求項1または2に記載のフェニレンエーテルオリゴマーであって、クロロホルム中で25℃においてウベローデ粘度計によって測定された、0.15デシリットル/グラム未満の固有粘度を有することを特徴とするフェニレンエーテルオリゴマー。
- 請求項1から3のいずれか1項に記載のフェニレンエーテルオリゴマーであって、ビニルベンゼンエーテル末端基を含むことを特徴とするフェニレンエーテルオリゴマー。
- 請求項1から4のいずれか1項に記載のフェニレンエーテルオリゴマーであって、構造
R1、R2、R3、およびR4は存在毎に、独立して、水素、ハロゲン、非置換もしくは置換C1〜C12一級もしくは二級ヒドロカルビル、C1〜C12ヒドロカルビルチオ、C1〜C12ヒドロカルビルオキシ、または少なくとも2個の炭素原子がハロゲン原子と酸素原子とを隔てるC2〜C12ハロヒドロカルビルオキシを含み;
zは、0または1であり;
Yは、
Rは各存在において、独立して、ビニルベンゼンエーテル末端基、アミン末端基、またはマレイミド末端基、ノルボルネン末端基、無水物基である]
を有することを特徴とするフェニレンエーテルオリゴマー。 - 請求項5に記載のフェニレンエーテルオリゴマーであって、R1およびR2の各存在がメチルであり、R3およびR4の各存在が水素であり、Yがイソプロピリデン基であり、Rがビニルベンジルエーテル基であることを特徴とするフェニレンエーテルオリゴマー。
- 請求項1から4のいずれか1項に記載のフェニレンエーテルオリゴマーであって、ポリシロキサンブロックを含むことを特徴とするフェニレンエーテルオリゴマー。
- 請求項1から7のいずれか1項に記載のフェニレンエーテルオリゴマーの製造方法であって、
触媒の存在下で2−メチル−6−シクロヘキシルフェノールを酸化重合して前記フェニレンエーテルオリゴマーを得る工程
を含むことを特徴とする方法。 - 請求項8に記載の方法であって、前記フェニレンエーテルオリゴマーを、ビニルベンゼンエーテル基、アミン基、マレイミド基、ノルボルネン基、無水物基、またはこれらのうち少なくとも1つを含む組合せと反応させ、官能化フェニレンエーテルオリゴマーを得る工程をさらに含むことを特徴とする方法。
- 硬化性組成物であって、
請求項1から7のいずれか1項に記載のフェニレンエーテルオリゴマー;および硬化促進剤
を含むことを特徴とする硬化性組成物。 - 請求項10に記載の硬化性組成物であって、前記硬化促進剤が、アミン、ジシアンジアミド、ポリアミド、アミドアミン、マンニッヒ塩基、無水物、フェノールホルムアルデヒド樹脂、カルボン酸官能性ポリエステル、ポリスルフィド、ポリメルカプタン、イソシアネート、シアネートエステル、またはこれらの組合せを含むことを特徴とする硬化性組成物。
- 請求項10または11に記載の硬化性組成物であって、補助硬化性樹脂、硬化性不飽和モノマー組成物、またはこれら両方をさらに含み、
好ましくは、ここで、前記補助硬化性樹脂が、エポキシ樹脂、シアネートエステル樹脂、マレイミド樹脂、ベンゾオキサジン樹脂、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、硬化性ビニル官能基を有するオリゴマーもしくはポリマー、またはこれらの組合せを含み、前記硬化性不飽和モノマー組成物が、一官能性スチレン化合物、一官能性(メタ)アクリル化合物、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、またはこれらの組合せを含む
ことを特徴とする硬化性組成物。 - 請求項10から12のいずれか1項に記載の硬化性組成物の硬化生成物を含む熱硬化組成物であって、好ましくは、180℃以上、好ましくは190℃以上、より好ましくは200℃以上のガラス転移温度を有することを特徴とする熱硬化組成物。
- 請求項13に記載の熱硬化組成物を含む物品であって、好ましくは、複合材料、発泡体、繊維、層、コーティング、封入剤、接着剤、封止剤、成形品、プリプレグ、ケーシング、積層体、金属張積層体、電子複合材料、構造用複合材料、またはこれらのうち少なくとも1つを含む組合せの形態であることを特徴とする物品。
- 熱硬化組成物の製造方法であって、請求項10から12に記載の硬化性組成物を、好ましくは50〜250℃の温度で硬化させる工程を含むことを特徴とする方法。
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