JP5682805B1 - フェノール性水酸基含有化合物、フェノール樹脂、硬化性組成物、その硬化物、半導体封止材料、及びプリント配線基板 - Google Patents
フェノール性水酸基含有化合物、フェノール樹脂、硬化性組成物、その硬化物、半導体封止材料、及びプリント配線基板 Download PDFInfo
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- JP5682805B1 JP5682805B1 JP2014535833A JP2014535833A JP5682805B1 JP 5682805 B1 JP5682805 B1 JP 5682805B1 JP 2014535833 A JP2014535833 A JP 2014535833A JP 2014535833 A JP2014535833 A JP 2014535833A JP 5682805 B1 JP5682805 B1 JP 5682805B1
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 2
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- 150000001639 boron compounds Chemical class 0.000 description 2
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- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 2
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- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
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- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- RXPAJWPEYBDXOG-UHFFFAOYSA-N hydron;methyl 4-methoxypyridine-2-carboxylate;chloride Chemical compound Cl.COC(=O)C1=CC(OC)=CC=N1 RXPAJWPEYBDXOG-UHFFFAOYSA-N 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- YSRVJVDFHZYRPA-UHFFFAOYSA-N melem Chemical compound NC1=NC(N23)=NC(N)=NC2=NC(N)=NC3=N1 YSRVJVDFHZYRPA-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- 235000019837 monoammonium phosphate Nutrition 0.000 description 1
- 239000006012 monoammonium phosphate Substances 0.000 description 1
- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical group C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical group 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002990 phenothiazines Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000003009 phosphonic acids Chemical class 0.000 description 1
- VBQCHPIMZGQLAZ-UHFFFAOYSA-N phosphorane Chemical class [PH5] VBQCHPIMZGQLAZ-UHFFFAOYSA-N 0.000 description 1
- 150000003012 phosphoric acid amides Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 239000001205 polyphosphate Substances 0.000 description 1
- 235000011176 polyphosphates Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- FOZHTJJTSSSURD-UHFFFAOYSA-J titanium(4+);dicarbonate Chemical compound [Ti+4].[O-]C([O-])=O.[O-]C([O-])=O FOZHTJJTSSSURD-UHFFFAOYSA-J 0.000 description 1
- 230000007704 transition Effects 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
- PZRXQXJGIQEYOG-UHFFFAOYSA-N zinc;oxido(oxo)borane Chemical compound [Zn+2].[O-]B=O.[O-]B=O PZRXQXJGIQEYOG-UHFFFAOYSA-N 0.000 description 1
Images
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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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
-
- 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
- C07C39/15—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 with all hydroxy groups on non-condensed rings, e.g. phenylphenol
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/62—Alcohols or phenols
- C08G59/621—Phenols
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
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- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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Abstract
Description
{式(x1)又は(x2)中、R1及びR2はそれぞれ炭素原子数1〜4のアルキル基、炭素原子数1〜4のアルコキシ基、アリール基又はアラルキル基の何れかであり、lは0〜3の整数、nは0〜4の整数である。lまたはnが2以上の場合、複数のR1又はR2は同一であっても良いし、それぞれ異なっていても良い。また、kは1〜3の整数、mは1又は2であり、Arは下記構造式(Ar1)
(式中、R3は炭素原子数1〜4のアルキル基、炭素原子数1〜4のアルコキシ基、アリール基又はアラルキル基の何れかであり、qは1〜4の整数である。qが2以上の場合、複数のR3は同一であっても良いし、それぞれ異なっていても良い。また、pは1又は2である。)
で表される構造部位である。k又はmが2以上の場合、複数のArは同一であっても良いし、それぞれ異なっていても良い。}
で表される構造部位である。]
で表される分子構造を有することを特徴とするフェノール性水酸基含有化合物に関する。
本発明のフェノール性水酸基含有化合物は、下記一般式(I)
{式(x1)又は(x2)中、R1及びR2はそれぞれ炭素原子数1〜4のアルキル基、炭素原子数1〜4のアルコキシ基、アリール基又はアラルキル基の何れかであり、lは0〜3の整数、nは0〜4の整数である。lまたはnが2以上の場合、複数のR1又はR2は同一であっても良いし、それぞれ異なっていても良い。また、kは1〜3の整数、mは1又は2であり、Arは下記構造式(Ar1)
(式中、R3は炭素原子数1〜4のアルキル基、炭素原子数1〜4のアルコキシ基、アリール基又はアラルキル基の何れかであり、qは1〜4の整数である。qが2以上の場合、複数のR3は同一であっても良いし、それぞれ異なっていても良い。また、pは1又は2である。)
で表される構造部位である。k又はmが2以上の場合、複数のArは同一であっても良いし、それぞれ異なっていても良い。}
で表される構造部位である。]
で表される分子構造を有することを特徴とする。
で表される化合物が挙げられ、具体的には、パラベンゾキノン、2−メチルベンゾキノン、2,3,5−トリメチル−ベンゾキノン、ナフトキノン等が挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。
で表される化合物が挙げられ、具体的には、オルソクレゾール、メタクレゾール、パラクレゾール、2,6−ジメチルフェノール、2,5−ジメチルフェノール、2,4−ジメチルフェノール、3,5−ジメチルフェノール、2,3,4−トリメチルフェノール、2,3,5−トリメチルフェノール、2,3,6−トリメチルフェノール、2,4,5−トリメチルフェノール、3,4,5−トリメチルフェノール、4−イソプロピルフェノール、4−tert−ブチルフェノール、2−メトキシフェノール、3−メトキシフェノール、4−メトキシフェノール、2‐メトキシ−4−メチルフェノール、2−tert−ブチル−4−メトキシフェノール、2,6−ジメトキシフェノール、3,5−ジメトキシフェノール、2−エトキシフェノール、3−エトキシフェノール、4−エトキシフェノール、2−フェニルフェノール、3−フェニルフェノール、4−フェニルフェノール、4−ベンジルフェノール等が挙げられる。これらはそれぞれ単独で用いても良いし、2種類以上を併用しても良い。
で表される構造部位である。k又はmが2以上の場合、複数のArは同一であっても良いし、それぞれ異なっていても良い。]
の何れかで表されるフェノール性水酸基含有化合物が挙げられる。
の何れか表される化合物が挙げられる。
<GPC測定条件>
測定装置 :東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.10」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8020モデルIIバージョン4.10」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
の何れかで表される化合物等が挙げられる。
[式中m、qはそれぞれ1または2であり、R4は炭素原子数1〜4のアルキル基、炭素原子数1〜4のアルコキシ基、アリール基又はアラルキル基の何れかであり、uは1〜4の整数である。uが2以上の場合、複数のR4は同一であっても良いし、それぞれ異なっていても良い。]
の何れかで表されるフェノール性水酸基含有化合物が挙げられる。
測定装置 :東ソー株式会社製「HLC−8220 GPC」、
カラム:東ソー株式会社製ガードカラム「HXL−L」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G2000HXL」
+東ソー株式会社製「TSK−GEL G3000HXL」
+東ソー株式会社製「TSK−GEL G4000HXL」
検出器: RI(示差屈折計)
データ処理:東ソー株式会社製「GPC−8020モデルIIバージョン4.10」
測定条件: カラム温度 40℃
展開溶媒 テトラヒドロフラン
流速 1.0ml/分
標準 : 前記「GPC−8020モデルIIバージョン4.10」の測定マニュアルに準拠して、分子量が既知の下記の単分散ポリスチレンを用いた。
(使用ポリスチレン)
東ソー株式会社製「A−500」
東ソー株式会社製「A−1000」
東ソー株式会社製「A−2500」
東ソー株式会社製「A−5000」
東ソー株式会社製「F−1」
東ソー株式会社製「F−2」
東ソー株式会社製「F−4」
東ソー株式会社製「F−10」
東ソー株式会社製「F−20」
東ソー株式会社製「F−40」
東ソー株式会社製「F−80」
東ソー株式会社製「F−128」
試料 : 樹脂固形分換算で1.0質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(50μl)。
装置:日本電子(株)製 AL−400
測定モード:SGNNE(NOE消去の1H完全デカップリング法)
溶媒 :ジメチルスルホキシド
パルス角度:45°パルス
試料濃度 :30wt%
積算回数 :10000回
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、オルソクレゾール649質量部(6.0モル)、パラベンゾキノン162質量部(1.5モル)、パラトルエンスルホン酸8質量部を仕込み、撹拌しながら室温から120℃まで昇温した。120℃に到達後、2時間攪拌した。反応終了後、析出した結晶物を渡別し、水200質量部で2回水洗した。その後加熱減圧条件下で乾燥してフェノール樹脂(1)117質量部得た。得られたフェノール樹脂(1)のGPCチャートを図1に、13CNMRスペクトルを図2、およびMSスペクトルを図3に示す。フェノール樹脂(1)の水酸基当量は81g/当量であり、MSスペクトルから下記構造式(a−1)で表される2核体化合物(x1)に相当する216のピーク、下記構造式(b−1)で表される3核体化合物(x2)に相当する322のピーク、下記構造式(c−1)で表される4核体化合物(x3)に相当する428のピークが検出された。GPCチャートから算出されるフェノール樹脂中の2核体化合物(x1)相当成分の含有量は4.6%、3核体化合物(x2)相当成分の含有量は88.0%、4核体化合物(x3)相当成分の含有量は5.1%であった。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、オルソクレゾール649質量部(6.0モル)、パラトルエンスルホン酸3質量部を仕込み、撹拌しながら室温から80℃まで昇温した。80℃に到達した後、パラベンゾキノン162質量部(1.5モル)を1時間要して添加し、その後更に130℃まで昇温し1時間攪拌して反応させた。反応終了後、減圧下乾燥し、フェノール樹脂(2)260質量部得た。得られたフェノール樹脂(2)のGPCチャートを図4に示す。フェノール樹脂(2)の水酸基当量は97g/当量であった。GPCチャートから算出されるフェノール樹脂中の2核体化合物(x1)相当成分の含有量は25.8%、3核体化合物(x2)相当成分の含有量は51.7%、4核体化合物(x3)相当成分の含有量は10.0%であった。
温度計、滴下ロート、冷却管、分留管、撹拌器を取り付けたフラスコに、2,6−ジメチルフェノール733質量部(6.0モル)、パラベンゾキノン216質量部(2.0モル)、パラトルエンスルホン酸9質量部を仕込み、撹拌しながら室温から120℃まで昇温した。120℃に到達後、2時間攪拌した。反応終了後、析出した結晶物を渡別し、水200質量部で2回水洗した。その後加熱減圧条件下で乾燥してフェノール樹脂(3)123質量部得た。得られたフェノール樹脂(3)のGPCチャートを図5に、MSスペクトルを図6に示す。フェノール樹脂(3)の水酸基当量は88g/当量であり、MSスペクトルから下記構造式(a−2)で表される化合物に相当する230のピーク、下記構造式(b−2)で表される化合物に相当する350のピーク、下記構造式(c−2)で表される化合物に相当する470のピークが検出された。GPCチャートから算出されるフェノール樹脂中の2核体化合物(x1)相当成分の含有量は8.0%、3核体化合物(x2)相当成分の含有量は87.8%、4核体化合物(x3)相当成分の含有量は1.6%であった。
先で得たフェノール樹脂(1)〜(3)及び比較対象用フェノール樹脂(1’)[トリフェニルメタン型フェノール樹脂(明和化成株式会社製「MEH−7500」水酸基当量98g/当量)]について、下記の要領で各種評価試験を行った。
1)評価サンプルの作成
前記フェノール樹脂(1)〜(3)、(1’)の何れかと、硬化剤としてナフタレン型エポキシ樹脂(DIC株式会社製「EXA−4750」エポキシ基当量188g/当量)、硬化促進剤としてトリフェニルホスフィン(以下「TPP」と略記する。)を用い、下記表2に示す組成で配合して硬化性組成物を得た。これを11cm×9cm×2.4mmの型枠に流し込み、プレスで150℃の温度で10分間成型した後、型枠から成型物を取り出し、次いで、175℃の温度で5時間後硬化させて評価サンプルを得た。
粘弾性測定装置(DMA:レオメトリック社製固体粘弾性測定装置RSAII、レクタンギュラーテンション法;周波数1Hz、昇温速度3℃/min)を用い、前記評価サンプルについて弾性率変化が最大となる(tanδ変化率が最も大きい)温度を測定し、これをガラス転移温度として評価した。結果を表1に示す。
1)評価サンプルの作成
前記フェノール樹脂(1)〜(3)、(1’)の何れかと、硬化剤としてナフタレン型エポキシ樹脂(DIC株式会社製「EXA−4750」エポキシ基当量188g/当量)、硬化促進剤としてトリフェニルホスフィン(以下「TPP」と略記する。)、無機充填材として球状シリカ(電気化学株式会社製「FB−5604」)、シランカップリング剤としてカップリング剤(信越化学株式会社製「KBM−403」)、カルナウバワックス(株式会社セラリカ野田製「PEARL WAX No.1−P」)、カーボンブラックを、下記表2に示す組成で配合し、2本ロールを用いて85℃の温度で5分間溶融混練して硬化性組成物を得た。得られた硬化性組成物を用い、トランスファー成形機にて幅12.7mm、長さ127mm、厚み1.6mm大のサンプルを175℃の温度で90秒成形した後、175℃の温度で5時間後硬化して評価用サンプルを得た。
先で得た厚さ1.6mmの評価用サンプル5本を用い、UL−94試験法に準拠して燃焼試験を行った。結果を表2に示す。
難燃試験クラス
*1:1回の接炎における最大燃焼時間(秒)
*2:試験片5本の合計燃焼時間(秒)
Claims (7)
- 下記一般式(I)
[式中Xは、下記構造式(x1)又は(x2)
で表される構造部位である。分子中の複数のArは同一であっても良いし、それぞれ異なっていても良い。}
で表される構造部位である。]
で表される分子構造を有し、前記一般式(I)においてk又はm+m’の値が1である2核体化合物(x1)と、前記一般式(I)においてk又はm+m’の値が2である3核体化合物(x2)とを含有するフェノール樹脂であって、フェノール樹脂中の前記2核体化合物(x1)の含有率がGPC測定における面積比率で2〜50%の範囲であり、かつ、前記3核体化合物(x2)の含有率がGPC測定における面積比率で10〜95%の範囲であることを特徴とするフェノール樹脂と、硬化剤とを必須成分とする硬化性組成物。 - 下記一般式(I)
[式中Xは、下記構造式(x1)又は(x2)
で表される構造部位である。分子中の複数のArは同一であっても良いし、それぞれ異なっていても良い。}
で表される構造部位である。]
で表される分子構造を有し、前記一般式(I)においてk又はm+m’の値が1である2核体化合物(x1)と、前記一般式(I)においてk又はm+m’の値が2である3核体化合物(x2)とを含有するフェノール樹脂であって、フェノール樹脂中の前記2核体化合物(x1)の含有率がGPC測定における面積比率で2〜50%の範囲であり、かつ、前記3核体化合物(x2)の含有率がGPC測定における面積比率で10〜95%の範囲であることを特徴とするフェノール樹脂と、エポキシ樹脂とを必須成分とする硬化性組成物。 - 前記フェノール樹脂が水酸基当量が70〜150g/当量の範囲にある請求項1〜3の何れかに記載の硬化性組成物。
- 請求項1又は2の何れかに記載の硬化性組成物を硬化反応させてなる硬化物。
- 請求項1又は2の何れかにに記載の硬化性組成物に加え、更に無機充填剤を含有する半導体封止材料。
- 請求項1又は2の何れかにに記載の硬化性組成物に有機溶剤を配合してワニス化した樹脂組成物を、補強基材に含浸し銅箔を重ねて加熱圧着させることにより得られたプリント配線基板。
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