JP7330865B2 - リン含有エポキシ樹脂及びその調製方法 - Google Patents
リン含有エポキシ樹脂及びその調製方法 Download PDFInfo
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- JP7330865B2 JP7330865B2 JP2019205784A JP2019205784A JP7330865B2 JP 7330865 B2 JP7330865 B2 JP 7330865B2 JP 2019205784 A JP2019205784 A JP 2019205784A JP 2019205784 A JP2019205784 A JP 2019205784A JP 7330865 B2 JP7330865 B2 JP 7330865B2
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- unsubstituted
- substituted
- alkyl group
- compound
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- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims description 33
- 229910052698 phosphorus Inorganic materials 0.000 title claims description 33
- 239000011574 phosphorus Substances 0.000 title claims description 33
- 238000000034 method Methods 0.000 title claims description 31
- 239000003822 epoxy resin Substances 0.000 title description 33
- 229920000647 polyepoxide Polymers 0.000 title description 33
- 238000002360 preparation method Methods 0.000 title description 6
- 239000000203 mixture Substances 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 85
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 42
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 33
- 125000003545 alkoxy group Chemical group 0.000 claims description 31
- -1 bisphenol compound Chemical class 0.000 claims description 29
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 29
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000003795 chemical substances by application Substances 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 229930185605 Bisphenol Natural products 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 8
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 6
- 239000004744 fabric Substances 0.000 claims description 6
- 230000009477 glass transition Effects 0.000 claims description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 4
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 4
- 239000011889 copper foil Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000001723 curing Methods 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000000758 substrate Substances 0.000 description 26
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- 239000007787 solid Substances 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 13
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000008199 coating composition Substances 0.000 description 11
- 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 11
- 239000004848 polyfunctional curative Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 7
- 239000004615 ingredient Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XZKLXPPYISZJCV-UHFFFAOYSA-N 1-benzyl-2-phenylimidazole Chemical compound C1=CN=C(C=2C=CC=CC=2)N1CC1=CC=CC=C1 XZKLXPPYISZJCV-UHFFFAOYSA-N 0.000 description 4
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004593 Epoxy Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 230000000269 nucleophilic effect Effects 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical group N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 3
- BSYJHYLAMMJNRC-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-ol Chemical compound CC(C)(C)CC(C)(C)O BSYJHYLAMMJNRC-UHFFFAOYSA-N 0.000 description 3
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 description 3
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 2
- IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 description 2
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
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- GLBHAWAMATUOBB-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diamine Chemical compound CC(C)(C)CCCCC(N)N GLBHAWAMATUOBB-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- 125000002252 acyl group Chemical group 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
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- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
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- KNDQHSIWLOJIGP-UMRXKNAASA-N (3ar,4s,7r,7as)-rel-3a,4,7,7a-tetrahydro-4,7-methanoisobenzofuran-1,3-dione Chemical compound O=C1OC(=O)[C@@H]2[C@H]1[C@]1([H])C=C[C@@]2([H])C1 KNDQHSIWLOJIGP-UMRXKNAASA-N 0.000 description 1
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- 150000003233 pyrroles Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical class OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- TWXMZYPORGXIFB-UHFFFAOYSA-N thiophene-3,4-dithiol Chemical compound SC1=CSC=C1S TWXMZYPORGXIFB-UHFFFAOYSA-N 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Substances SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000006168 tricyclic group Chemical group 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
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- C08G59/4028—Isocyanates; Thioisocyanates
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Description
aは、1~5の整数であり;
bは、0~5の整数であり;
R5は、C1~C10の非置換アルキル基、C1~C10の置換アルキル基、C1~C10の非置換アルコキシ基、C1~C10の置換アルコキシ基、C3~C10の非置換シクロアルキル基、C3~C10の置換シクロアルキル基及びAr3からなる群より独立して選択され、そのうちAr3は、下記からなる群より選択され;
R8は、存在しないか、又は、-CH2-、-(CH3)2C-、-CO-、-SO2-及び-O-からなる群より選択され;かつ
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~20の整数である。
式中、
aは、1~5の整数であり;
bは、0~5の整数であり;
R5は、C1~C10の非置換アルキル基、C1~C10の置換アルキル基、C1~C10の非置換アルコキシ基、C1~C10の置換アルコキシ基、C3~C10の非置換シクロアルキル基、C3~C10の置換シクロアルキル基及びAr3からなる群より独立して選択され、そのうちAr3は、下記からなる群より選択され;
R8は、存在しないか、又は、-CH2-、-(CH3)2C-、-CO-、-SO2-及び-O-からなる群より選択され;かつ
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~20の整数である。
本発明の1つの実施態様には、式(I)の化合物が含まれる。
aは、1~5の整数であり;
bは、0~5の整数であり;
R5は、C1~C10の非置換アルキル基、C1~C10の置換アルキル基、C1~C10の非置換アルコキシ基、C1~C10の置換アルコキシ基、C3~C10の非置換シクロアルキル基、C3~C10の置換シクロアルキル基及びAr3からなる群より独立して選択され、そのうちAr3は、下記からなる群より選択され;
R8は、存在しないか、又は、-CH2-、-(CH3)2C-、-CO-、-SO2-及び-O-からなる群より選択され;かつ
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~20の整数である。
本発明の別の実施態様では、式(I)の化合物の調製方法を提供する。その方法は、反応スキーム(I)に従い、式(II)の化合物を、式(III)の化合物及び少なくとも1つの触媒と接触させるものである。
aは、1~5の整数であり;
bは、0~5の整数であり;
R5は、C1~C10の非置換アルキル基、C1~C10の置換アルキル基、C1~C10の非置換アルコキシ基、C1~C10の置換アルコキシ基、C3~C10の非置換シクロアルキル基、C3~C10の置換シクロアルキル基及びAr3からなる群より独立して選択され、そのうちAr3は、下記からなる群より選択され;
R8は、存在しないか、又は、-CH2-、-(CH3)2C-、-CO-、-SO2-及び-O-からなる群より選択され;かつ
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~20の整数である。
式(II)のリン含有ビスフェノール化合物については、先に詳述したとおりである。
式(III)のジイソシアネート(diisocyanate)化合物については、先に詳述したとおりである。
この方法においては、多種多様な触媒を使用することができる。本明細書では、触媒は、式(II)のリン含有ビスフェノール化合物と式(III)のジイソシアネート化合物との付加反応を促進するものと定義する。触媒に適するのは、例えば、2-メチルイミダゾール(2MI)、2-フェニルイミダゾール(2PI)、2-エチル-4-メチルイミダゾール(2E4MZ)、1-ベンジル-2-フェニルイミダゾール(1B2PZ)、ホウ酸、トリフェニルホスフィン(TPP)、テトラフェニルホスホニウムテトラフェニルボラート(TPP-k)、リチウム化合物又はこれらの組み合わせであるが、これらの例示に限定されない。
その他の実施例において、式(I)の化合物の調製方法において、選択的に少なくとも1つの溶剤を使用することができる。この方法において有用な溶剤は、例えば、ケトン、環状ケトン、エーテル、芳香族炭化水素、アルコールエーテル、及びこれらの組み合わせから選択することができる。溶剤に適するのは、例えば、酢酸n-プロピル、酢酸n-ブチル、キシレン、オルソキシレン、メタキシレン、パラキシレン、(モノ)プロピレングリコール(モノ)メチルエーテル(PM)、アセトン、メチルエチルケトン、メチルイソブチルケトン、エチルイソブチルケトン、N-メチルピロリドン、ジメチルホルムアミド、ジメチルスルホキシド、及びこれらの混合物であるが、これらの例示に限定されない。1つの好ましい実施例では、この方法において有用な少なくとも1つの溶剤は、メチルエチルケトンである。
式(I)の化合物は、式(II)のリン含有ビスフェノール化合物、式(III)のジイソシアネート化合物、少なくとも1つの触媒及び少なくとも1つの任意の溶剤で形成された反応混合物により調製することができる。これらの成分は、同時、順に又は任意の順序で添加してよい。これらの成分は、任意の公知の混合設備又は反応容器中で、混合物が均質となるまで混合すればよく、これにより硬化性組成物を製造する。
通常、式(I)の化合物は、固形である。均一性を得るため、本発明の式(I)の化合物を溶剤に溶解し、かつ、高固形分(例えば、少なくとも60wt%)になるよう調整することができる。多くの実施例において、この化合物の固形分は、少なくとも60wt%、少なくとも70wt%、又は、70wt%超であってよい。
本発明の別の実施態様では、硬化性組成物を提供する。この硬化性組成物には、(a)少なくとも1つの式(I)の化合物、及び、(b)少なくとも1つの硬化剤が含まれる。この硬化性組成物は、さらに、少なくとも1つの溶剤、少なくとも1つの添加剤、又は、これらの組み合わせを含むことができる。1つの実施例において、この硬化性組成物は、液体であってよい。別の実施例において、この硬化性組成物は、半固体状態又は固体状態であってよい。これら半固体状態又は固体状態の硬化性組成物は、「プリプレグ」と称することができる。
少なくとも1つの式(I)の化合物については、前記[I]において詳述したとおりである。
少なくとも1つの硬化剤(即ち成分(b)、固化剤又は架橋剤とも称する)は、硬化性組成物(硬化性塗料組成物)の調製に用いることができる。硬化剤に適するのは、例えば、無水物硬化剤、酸硬化剤、アミン硬化剤、ピリジン硬化剤、ルイス酸、フェノール類硬化剤、アルコール硬化剤、イミダゾール硬化剤、硫黄硬化剤(メルカプタン)又はこれらの混合物であるが、これらの例示に限定されない。幾つかの実施例において、ルイス酸は、上述の硬化剤と組み合わせて使用することができる。その他の実施例において、硬化剤は、例えば、エポキシ反応性リン化合物(H-PRR’)、求核性アニオンを有する第四級アンモニウム塩、求核性アニオンを有する第四級ホスホニウム塩、求核性アニオンを有する第三級アルセニウム塩、ホウ酸を含む化合物、及び求核性アニオンを有する第三級スルホニウム塩等の求核性物質でよい。
硬化性塗料組成物(硬化性組成物)の調製には、さらに少なくとも1つの触媒、即ち成分(c)を含めてもよい。少なくとも1つの触媒として使用可能なものには、例えばホウ酸や、トリフェニルホスフィン(TPP)、エチルトリフェニルホスフィン(ETPPI)及びテトラフェニルホスホニウムテトラフェニルボラート(TPP-k)から選択されるホスフィン化合物等、多様な種類が含まれる。
硬化性組成物は、さらに、少なくとも1つの任意の溶剤を含むことができる。この硬化性組成物に適する溶剤については、前記セクション[II](d)中で詳述したとおりである。1つの好ましい実施例では、メチルエチルケトンを溶剤とすることができる。
硬化性組成物は、さらに、1種類以上の顔料及び/又はその他の添加剤を含むことができ、これは、硬化性組成物の調製、保存、応用及び硬化に用いることができる。添加剤に適するものには、填料、均染剤、及びこれらの類似物又はこれらの組み合わせが含まれる。
硬化性組成物は、式(I)の化合物、少なくとも1つの硬化剤、少なくとも1つの任意の溶剤及び少なくとも1つの任意の添加剤で形成された反応混合物により調製することができる。これらの成分は、同時、順に又は任意の順序で添加してよい。これらの成分は、任意の公知の混合設備又は反応容器中で、混合物が均質となるまで混合すればよく、これにより硬化性組成物を製造する。
本発明の別の実施態様では、硬化性組成物の硬化方法及び硬化組成物の性質を提供する。この方法には、前記セクション[III]中で詳述した硬化性組成物を提供し、硬化性組成物を基材に塗布するか、又は多層の半固体状態もしくは固体状態であるプリプレグの基質を構築した後、組成物を硬化することが含まれる。
硬化性組成物に適するものについては、前記セクション[III]で説明したとおりである。
硬化性組成物は、基材上に塗布することができる。広義において、基材は一種の材料と定義され、そのうち硬化性組成物は、最初に基材の少なくとも1つの表面の少なくとも一部に塗布される。基材は、硬化塗膜が形成される硬化に耐え得る任意の材料でよい。
この方法はさらに、硬化性組成物を基材の少なくとも1つの表面の一部に塗布することを含む。基材に適するものについては、先に詳述したとおりである。硬化性組成物の塗布については、例えば液体の硬化性組成物であれば、コンラージ棒、ローラー、ナイフ、塗料用刷毛、スプレー、浸漬又は当業者に公知な他の方法を用いて塗布することができ、また、半固体状態又は固体状態の硬化性塗料組成物(プリプレグ)を様々な寸法にカットして基材上に置くこともでき、様々な方式で塗布することができる。さらに、硬化性組成物を1回以上塗布して多層塗膜を形成することもできる。前記のとおり、硬化性組成物を塗布対象である基材の1つ以上の表面に塗布することもできる。
通常、硬化性組成物は、当業者に公知な多くの方法を用いて硬化することができ、これには、熱、フリーラジカル開始、紫外線又はこれらの組み合わせが含まれるが、これらの例示に限定されない。1つの好ましい実施例において、硬化性組成物は、熱で硬化させる。
この硬化組成物は、低燃焼性、低毒性、良好な加工特性及び各種材料との良好な相容性を示す。
本明細書が実施例の要素の紹介において記す冠詞の「a/an(1つの)」、「the(当該)」及び「said(前記)」は、1つ以上の要素が存在することを示している。用語の「含む」、「包含する」及び「有する」は、包含的であることを示し、列挙する要素以外の他の要素も存在し得ることを示している。
実施例3と同じ方法で合成した。ただし、MDI1の代わりに使用したジイソシアネートはMDI2である。
実施例3と同じ方法で合成した。ただし、MDI1の代わりに使用したジイソシアネートはMDI3(式(III)として使用。式中のAは式(XX)である)である。
63.3gのDMP(実施例1)及び100gのエポキシ樹脂1を、ジャケットヒーター、温度調節器、電動撹拌器並びに撹拌子、窒素供給口、熱電対、水冷凝縮器及び供給用漏斗が設けられた5つ口のガラス反応釜中に入れた。窒素ガス中で、反応釜を130℃まで加熱した。DMP及びエポキシ樹脂1が完全に融解し、真空下で乾燥させた後、窒素ガス下で0.7gの触媒Aを導入した。温度を170℃まで上げて、2.5時間維持した。硬化性化合物(比較例1)が形成された。均一性を確保するため、生成物をMEK中に溶解し、かつ、固形分を65%に調整した。
実施例3と同じ方法で合成した。ただし、DMPEの代わりにエポキシ樹脂2を使用し、MDI1は使用しなかった。
実施例3と同じ方法で合成した。ただし、DMPEの代わりにエポキシ樹脂2を使用し、MDI1の代わりに5gのMDI2を使用した。
実施例3と同じ方法で合成した。ただし、DMPEの代わりにエポキシ樹脂3を使用し、MDI1は使用しなかった。
・エポキシ当量(EEW)(g/eq):
ASTM D1652に記載の方法に準拠してエポキシ樹脂試料を測定に供した。
・固形分(%):
リン含有エポキシ樹脂が含まれた1gの試料を、150℃のオーブンに60分間入れた後、得られた不揮発性成分の重量比率を測定した。
・リン含有量(重量%):
濃度の異なるリン酸二水素カリウム溶液のセットから、波長420nmにおける紫外可視吸収の検量線を作成した。硫酸及び過硫酸カリウムをエポキシ樹脂試料に添加した。100℃の温度下で60分間消化させた後、モリブドバナジウム酸塩試薬で処理して消化させた試料溶液により、バナドモリブドリン酸を形成した。波長420nmにおける紫外可視吸収で試料を測定した。検量線からリン含有量を求め、質量%を単位とした。
・オキサゾリドン含有量(eq/kg):
オキサゾリドン環状構造は、エポキシ樹脂及びイソシアネートを合成したものである。したがって、オキサゾリドン含有量は、以下の式に示すとおり、エポキシ樹脂の消費量から換算して得た。
オキサゾリドン含有量
=((樹脂重量/EEW0)-(生成物重量/EEW1))/(生成物重量)×1000
EEW0:エポキシ反応物のエポキシ当量
EEW1:生成物のエポキシ当量
実施例3~5及び比較例1~4の硬化性化合物(リン含有エポキシ樹脂)をガラス繊維織物(GF-7628)に浸漬し、かつ、160℃で乾燥させて、プリプレグを形成した。5片のプリプレグを積層し、頂部及び底部それぞれに35μmの銅箔を1枚置いた。この構造物を温度210℃、圧力25kg/cm2でラミネートし、積層体を得た。得られた積層体には、リン含有エポキシ樹脂及びガラス繊維織物が含まれている。
・難燃性:
以下の表4に示す「UL94難燃性等級」に基づいて判定した。
・分解温度(Decomposition Temperature、Td、5%重量損失):
IPC-TM-650-2.3.40に基づき、熱重量分析装置(Thermogravimetric Analyzer、TGA)で測定した(走査速度:10℃/分)。
・難燃性(Ttotal)(秒)及び(Tmax)(秒):
UL94に基づいて測定した。
・ガラス転位温度Tg(DSC)(℃):
IPC-TM-650-2.4.25に基づき、示差走査熱量計(Differential Scanning Calorimetry、DSC)で測定した(走査速度:20℃/分)。
・ガラス転位温度Tg(DMA)(℃):
IPC-TM-650-2.44.4に基づき、動的機械分析(Dynamic Mechanical Analysis、DMA)で測定した(走査速度:2℃/分)。
・熱安定性(はんだ耐熱性)(S-288)(秒):
JIS-C-6481にしたがい、積層体を288℃のはんだ炉内に浸し、層の剥離時間を測定した。
・熱膨張係数(Coefficient of Thermal Expansion、CTE)(ppm/K):
IPC-TM-650-2.4.24に基づき、熱機械分析(Thermomechanical Analysis、TMA)で測定した。
α1:Tg前のCTE
α2:Tg後のCTE
・剥離強度(1oz銅)(kgf/cm):
IPC-TM-650-2.4.8に基づいて測定した。
・吸水率(wt%):
試料を100℃の水に入れ、2時間後に重量の増加(wt%)を測定した。
・誘電率(Dk)(1MHz)及び誘電正接(Df)(1MHz):
IPC-TM-650-2.5.5.9に基づいて測定した。
Claims (20)
- 式(I)の化合物:
aは、1~5の整数であり;
bは、0~5の整数であり;
R5は、C1~C10の非置換アルキル基、C1~C10の置換アルキル基、C1~C10の非置換アルコキシ基、C1~C10の置換アルコキシ基、C3~C10の非置換シクロアルキル基、C3~C10の置換シクロアルキル基及びAr3からなる群より独立して選択され、そのうちAr3は、下記からなる群より選択され;
R8は、存在しないか、又は、-CH2-、-(CH3)2C-、-CO-、-SO2-及び-O-からなる群より選択され;かつ
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~20の整数である。 - R5は、C1~C6の非置換アルキル基又はC1~C6の置換アルキル基である、請求項1に記載の化合物。
- Ar1及びAr2は、それぞれ独立して
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~4の整数である、請求項1に記載の化合物。 - R6は、水素であり、かつ、R9は、存在しない、請求項3に記載の化合物。
- Aは、
R6は、H、C1~C6の非置換アルキル基及びC1~C6の置換アルキル基からなる群より独立して選択される、請求項1に記載の化合物。 - R1、R2、R3及びR4は、出現毎に、H、C1~C4の非置換アルキル基及びC1~C4の置換アルキル基からなる群よりそれぞれ独立して選択される、請求項1に記載の化合物。
- リン含有量が、少なくとも3.5wt%である、請求項1に記載の化合物。
- オキサゾリドン(oxazolidone)含有量が、少なくとも0.4eq/kgである、請求項1に記載の化合物。
- 式(I)の化合物の調製方法であって、
式中、
aは、1~5の整数であり;
bは、0~5の整数であり;
R5は、C1~C10の非置換アルキル基、C1~C10の置換アルキル基、C1~C10の非置換アルコキシ基、C1~C10の置換アルコキシ基、C3~C10の非置換シクロアルキル基、C3~C10の置換シクロアルキル基及びAr3からなる群より独立して選択され、そのうちAr3は、下記からなる群より選択され;
R8は、存在しないか、又は、-CH2-、-(CH3)2C-、-CO-、-SO2-及び-O-からなる群より選択され;かつ
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~20の整数である、方法。 - R5は、C1~C6の非置換アルキル基又はC1~C6の置換アルキル基である、請求項9に記載の方法。
- Ar1及びAr2は、それぞれ独立して
R9は、存在しないか、又は、-(CH2)p-であり、そのうちpは、1~4の整数である、請求項9に記載の方法。 - Aは、
R6は、Hである、請求項9に記載の方法。 - 式(II)の化合物と式(III)の化合物との重量比は、20.0:1.0~5.0:1.0である、請求項9に記載の方法。
- 少なくとも1つの触媒が、イミダゾール(imidazole)を含み、かつ、
式(II)のリン含有ビスフェノール化合物と触媒との重量比は、500:1~50:1である、請求項9に記載の方法。 - 硬化性組成物を硬化させてなる硬化組成物であって、
前記硬化性組成物は、
a.少なくとも1つの請求項1に記載の化合物;
b.少なくとも1つの硬化剤;及び
c.少なくとも1つの触媒
を含む、硬化組成物。 - 前記硬化性組成物は、少なくとも1つの溶剤、少なくとも1つの添加剤又はこれらの組み合わせをさらに含む、請求項15に記載の硬化組成物。
- 示差走査熱量計(Differential Scanning Calorimetry、DSC)にて測定したガラス転位温度(Glass Transition Temperature、Tg)が180℃よりも高い、請求項15に記載の硬化組成物。
- 硬化性組成物を硬化させてなる硬化組成物であって、
前記硬化性組成物は、
a.少なくとも1つの請求項1に記載の化合物;
b.少なくとも1つの硬化剤;
c.少なくとも1つの触媒;
d.少なくとも1つの銅箔;及び
e.少なくとも1つの繊維布
を含む、硬化組成物。 - UL94(米国Underwriters Laboratories社公表のプラスチック材料燃焼性規格)に基づいて測定した、Ttotalが10秒未満であり、かつ、Tmaxが4秒未満である、請求項18に記載の硬化組成物。
- IPC-TM-650-2.5.5.9に基づいて測定した、誘電率(Dk)が4.8未満であり、かつ、誘電正接(Df)が0.020未満である、請求項18に記載の硬化組成物。
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